The 99 Greatest Jay-Z Songs, Ranked

Thirty years in: the highs, the lows, the A-Rod numbers.

Art by DJ Short

This coming weekend, Jay-Z will play a trio of shows at Yankee Stadium, one celebrating the 30th anniversary of his beloved debut album, Reasonable Doubt, another dedicated to The Blueprint, his signature album from 2001 that was somehow not written out of history despite dropping on the bloodiest day in his hometown’s modern history. (The third was dubbed “Extra Innings.”) Later this summer he’s got gigs in Paris and Los Angeles; in March he sat for an expansive interview with Frazier Tharpe at GQ. There’s a docuseries coming to HBO in the fall. Maybe something—an album, a full tour slate, a Super Bowl performance—is in the works; maybe this is, in fact, simply a celebration to mark the passage of time.

In either case, we’re making the days leading up to those Yankee Stadium shows Jay-Z Week at POW. Later we’ll be publishing definitive essays on the two albums Jay will play in full this weekend; we’ll also be taking a look into the courtroom and ranking his solo LPs. Today, we present the 99 greatest Jay-Z songs, ranked and considered by some of the best critics alive today.

99. Empire State of Mind f/ Alicia Keys
prod. Al Shux, Janet Sewell, and Angela Hunte
The Blueprint 3 [2009]

Jay’s the “new Sinatra”? Yeah right. But this June, opening a season of mega-watt New York pride—Knicks victory, a historic rent freeze, DSA’s primary sweep—the people decided. Right after the clock ran out on Game 5, the song spread through the city’s streets fast as a final-second tap-in at the hand of God. It was neither “N.Y. State of Mind,” nor “New York State of Mind,” nor “New York, New York”—it was the schmaltzy big-apple platitudes of CONCRETE JUNGLE WHERE DREAMS ARE MADE OF THERE’S NOTHING YOU CAN’T DO that no New Yorker was above. I was in Von King Park in Bed-Stuy, about 10 blocks from Marcy Houses, and three different congregations of hundreds if not thousands of people were screaming BIG LIGHTS WILL INSPIRE YOU NOW YOU’RE IN NEW YORK in an adrenaline-fueled delirium (conveniently drowning out the song’s more embarrassing bars) like the city’s win depended on it. Jay didn’t craft that made-for-Broadway chorus—it was written in London by two native Brooklynites, Angela Hunte and Janet Sewell-Ulepic—but he took it to the top of the charts, and brought it home. —JENN PELLY

98. Blueprint (Momma Loves Me)
prod. Bink
The Blueprint [2001]

The extended block party that is “Izzo” aside, The Blueprint has always been, for me, a winter album, and that’s never felt more acutely than on its eerily intimate, downbeat closing song. For someone so practiced, by this point, at moving through pop song formats, it’s fascinating how Jay unspools toward the very end: pleas to two proteges to trust him a little bit longer, his mother’s love wielded like a revolver. But what it’s really about is the one line in the Jay-Z catalog placed at an artificial distance through a brief shock of Autotune: “I was brought up in pain, y’all can’t touch me.” —PAUL THOMPSON

97. Get Throwed
prod. Mr. Lee
Bun B’s Trill [2005]

In 2005, Jay-Z ascended to a corner office while Pimp C stayed stuck in a cell, Audemars Piguet partnerships toasting the newly minted Def Jam CEO as Sweet Jones counted the days on rosary beads.

Intersecting both worlds was J Prince. The Rap-A-Lot founder was tasked with steering solo careers for the incarcerated Mack and his partner, Bun B. Flying four hours to New York, Prince personally played Bun’s solo debut for the Purple Label poet laureate. “Pushin’” piqued Jay’s interest, but ultimately it was “Get Throwed,” a late-’90s UGK outtake salvaged from a hard drive by Mr. Lee, that landed the feature.

Reproduced on Lee’s laptop with aggro guitars, live drums, and a spaced-out soundscape, Southern rap’s rubric shifted for years to follow. The clock-in, pour-up posse cut solidified Bun’s solo start, broke Mike Dean disciple Z-Ro beyond an Ozone audience, and elevated an emergent Young Jeezy. More importantly, it built buzz for a soon-to-be-free Chad Butler, allowing President Carter the rare chance to touch soil and grip grain. —IAN STONEBROOK

96. Can I Live II f/ Memphis Bleek
prod. K-Rob
Reasonable Doubt reissue bonus track [1998]

On “Coming of Age,” Bleek plays his part perfectly. But in the ecosystem of Jay-Z albums, his identity became almost exclusively that of the archetypal protege, useful for the threat he allegedly posed, an extension of empire. So it’s a relief to hear him here, cutting loose, the strain in his voice misdirection for how comfortably he sits in the pocket. And to think he “knew all about a dope fiend before reading Donald Goines.” —PAUL THOMPSON

95. Blue Magic
prod. The Neptunes
American Gangster [2007]

I know what happened: Kingdom Come was Kingdom Come, Wayne blotted out the sun. People were rightfully a little leery of late-middle period Oliver Stone. But while Jay’s American Gangster was well received by critics and treated, in the last decade or so, to some light canonization, that rehabilitation did not extend as far as the album’s lead single, which was bizarrely shunted into bonus-track purgatory. In any event: “Blame Reagan for making me to a monster/Blame Oliver North and Iran-Contra/I ran contraband that they sponsored/Before this rhyming stuff, we was in concert.” —PAUL THOMPSON

94. Flip Flop Rock
prod. Big Boi and Mr. DJ
Outkast’s Speakerboxxx/The Love Below [2003]

This sneakily foreboding cut from deep into Big Boi’s half of the strangest Diamond-selling rap album finds Jay at wonderful tonal odds with the Atlantans. Where he has always been comfortable pulling from soul or Blaxploitation or the Panthers with a wink, Outkast seems ready to embody those or any other sociocultural factions in three-minute bursts. And so Jay’s “shout out to public housing” is made to seem just that much grimmer, a stubborn tether to objective reality. —PAUL THOMPSON

93. Seen It All
prod. Cardo
Jeezy’s Seen It All: The Autobiography [2014]

A year after Magna Carta Holy Grail was written off as safe and staid, Jeezy pushed Jay out of complacency, formally and substantively. Jay’s verse on “Seen It All” apparently brought the billionaire to tears as he wrote. It’s easy to see why. Confidants get locked up or shot, but Jay eludes both fates, the sole survivor of a fallen empire. “Now the Nets a stone throw from where I used to throw bricks/So it’s only right I’m still tossin’ ‘round Knicks,” he raps with evident pride. —JOSH SVETZ

92. Is That Yo Bitch f/ Missy Elliott and Twista
prod. Timbaland
Vol. 3... Life and Times of S. Carter [European edition] [1999]

Tempting as it may be to pair this with the portentous last line of the Nas verse on “Takeover” as solely a precursor to “Supa Ugly,” “Is That Yo Bitch” is in fact a dispatch from the outer reaches of Timbaland’s hip-hop vision, a song governed by a single musical idea: the catharsis of Missy saying the title phrase. The thunderous drums and rubberband-taut flows (Twista is a sincerely brilliant bit of stunt casting) are simply foreplay. —PAUL THOMPSON

91. Fallin’
prod. Jermaine Dupri and No I.D.
American Gangster [2007]

Whether it’s Tommy DeVito walking into that empty room or Tony Montana grimacing at his white-stained CCTV monitor, every classic gangster movie has a pivotal scene where the male protagonist finally realizes the jig is up. “Fallin” is that capitulation literalized and condensed. Staggered strings and Bilal’s bittersweet harmonies create a regal if slightly morose atmosphere, as Jay-Z toasts to a lifetime of lessons gleamed from the criminal underworld. “You see what that last run did to De Niro” he raps—with genuine sadness, as if it was his own flesh and blood that got clapped at the end of Heat. —THOMAS HOBBS

90. Crazy in Love
prod. Beyoncé and Rich Harrison
Beyoncé’s Dangerously in Love [2003]

For a song ostensibly about the psychic torture of infatuation, Jay and Bey sound utterly exultant on “Crazy In Love.” The bombastic, brassy follow up to their 2002 collaboration “03 Bonnie & Clyde” booms with the feverish exuberance of finally finding someone who matches your freak. Anchored by the nearly regal horns of the Chi-Lites’ “Are You My Woman (Tell Me So)” and Beyoncé’s universally singable “uh-oh” refrain, “Crazy In Love” is the sound of a power couple declaring their dominance: Bey, the counterintuitively sensitive diva; Jay, the casually confident muse. —ARIELLE GORDON

89. Breathe Easy (Lyrical Exercise)
prod. Just Blaze
The Blueprint [2001]

As someone whose interviews are hotter, I approve. —PAUL THOMPSON

88. Moment of Clarity
prod. Eminem & Luis Resto
The Black Album [2003]

Legacy and self-reference have always been twin obsessions of Jay-Z the writer; those concerns reached their zenith on the faux-retirement boasts and blues of The Black Album. “Moment of Clarity” embraces this duality with twisty name-drops of his entire pre-2003 discog and proselytizing for the Roc, in that Jay himself is the synecdochic nucleus of the label. The stiff melodrama of the extremely of-the-era Eminem beat makes perfect bedfellows with the regal record-setting—if this is the last time, it might as well be honest. Jay saves the rest of his regard for family, blood (forgiving his absentee father and recognizing the systemic causes) or chosen (mourning Beanie’s incarceration and the still-burning wound of Biggie’s passing). He’s a disciple of his own history, rarely more devout than here.—ALY ELEANOR

87. Best of Me, Part 2
prod. Trackmasters
DJ Clue?’s Backstage: A Hard Knock Life [2000]

On the surface, “Best of Me (Pt. 2)” is a quintessential if unremarkable R&B teamup plopped within yet another DJ Clue mixtape. With no offense to Mya, it lacks the crossover flirtatiousness of past and future Jay features on hits like “Heartbreaker,” “Crazy in Love,” “Drunk in Love,” and “Frontin.’” Yet none of those songs have Jay rapping with this much flair, force, and, oddly, annoyance. “Have an affair, act like an adult for once,” he huffs on his bravura second verse. That impatience even extends to the song itself; he’s almost pissed that he’s there to begin with: “High school crossover, waved away picks/Music is the same shit, gave away hits.” That unexpected tension–talking this reckless on a playful love song, overtures discarded for demands and dismissals–makes these two verses unforgettable. (Also unforgettable: Mya pioneering the jersey dress in the video). —JACKSON HOWARD

86. Money, Cash, Hoes f/ DMX
prod. Swizz Beatz
Vol. 2... Hard Knock Life [1998]

On most of these songs that comprise Jay and DMX’s on-wax rivalry, Jay steps into X’s lane, mustering his most aggressive rhymes. (This was before Jay vacationed with Gwenyth Paltrow and the guy from Coldplay.) “Money, Cash, Hoes” is the apotheosis of Jay’s durag-and-throwback jersey era, a bouquet of ignorance over a pounding Swizz Beatz production tailored to the 1999 Summer Jam stage. But DMX does not and cannot pantomime Jay-Z, so X’s verse is oblivious to the fact that this is a song about money and sex. In 2019, X told GQ that he did not make songs for the club. “You give me a beat that people can dance to? I’ll spit some shit that a motherfucker can beat somebody up to. It’s a good combination.” —EVAN NABAVIAN

85. Time to Build
prod. Irv Gotti
Mic Geronimo’s The Natural [1995]

There’s a lot to be written about Mic Geronimo specifically as a natural link between eras who has retroactively been made to sound unstuck in time. And on “Time To Build,” it’s particularly disorienting to hear Ja Rule sound as if he’s a rapper from 1991. But this is Babe Ruth calling his shot, an untreated schizophrenia-era Gucci Mane level of artist A&Ring. —PAUL THOMPSON

84. What More Can I Say
prod. The Buchanans
The Black Album [2003]

There’s nothing to say sometimes. You just have to listen to those drums: Bum ba bum ba buuuuum. And the melody in lockstep with the rhythm. And at the time, maybe he wasn’t ever going to say anything else ever again, although of course he always was. —WILL HAGLE

83. Blackout
prod. Swizz Beatz
DMX’s Flesh of My Flesh, Blood of My Blood [1998]

Though “Blackout” opens with a Platonic-ideal Jadakiss line (“I used to have bad luck”) and no one on the song is less than actually great, this belongs to Jay, the monster who sleeps whole winters, wakes up spits summers, the “ghetto n—— putting up Will Smith numbers.” What he takes from Kiss is the trick of using a switch in the rhyme scheme to give a verse forward momentum, as if each minute shift in what Elaine May would call the ecology of the thing is a cataclysmic event—because of course it is. —PAUL THOMPSON

82. December 4th
prod. Just Blaze
The Black Album [2003]

This is the rare Jay-Z song that’s not really about Jay-Z. That sounds insane—the first vocals are “Shawn Carter was born December 4th, weighing in at ten pounds, eight ounces.” But our protagonist, the diamond skyscraper emcee, suddenly feels so small here. He’s swaddled by the careful Gloria Carter and cries for the wayward Adnis Reeves. He’s a redshirt freshman under DeHaven Irby, then Spanish Jose. Bike and boombox become foreground. Just Blaze’s majestic Chi-Lites flip towers over the flow. All together, it’s a cufflinked sleight of hand that turns subject to object. It’s not the life he chose, but the life that chose him. —STEVEN LOUIS

81. Beware of the Boys (Remix)
prod. Panjabi MC
single [2003]

With “Beware of the Boys,” Jay-Z forever earned some goodwill with (and exasperation from) the 21^st century desi diaspora. It started in the late ’90s, when the England-born Panjabi MC roped folk singer Labh Janjua in to an innovative sonic cocktail: a loop of clattering dhols and a tumbi, fused with a rework of Busta Rhymes’ “Fire It Up” beat that turned the Knight Rider bassline all the way up. It was a combo so irresistible, so thumping, that it became a sleeper hit in dancefloors across Europe—including in Switzerland, where Jay-Z happened to hear the track. His remix singlehandedly brought Panjabi MC’s greatest hit into the States, complete with some corny Orientalism (“Move your body like a snake, Mama!”) and a bit of international consciousness (“We back home, screaming ‘Leave Iraq alone!’”). Decades later, you’ve probably heard it everywhere, from your college pal’s sangheet, to your favorite movie soundtrack, to some of the strangest TikToks on the web. —NITISH PAHWA

80. Heartbreaker
prod. Mariah Carey, DJ Clue?, and Ken “Duro” Ifill
Mariah Carey’s Rainbow [1999]

What a gift it was to Jay-Z when the English language osmosed the word jacuzzi. —PAUL THOMPSON

79. N——s in Paris
prod. Hit-Boy, co-prod. Mike Dean & Kanye West
Watch the Throne [2011]

Now that we’re well over a decade removed from its ubiquity, the thing that strikes me most about this song is that it’s one of the weirdest beats Jay has ever flowed on, and this is a guy who once rapped over a Cake sample, multiple M.I.A. songs, and whatever Timbaland’s beat for “Ghetto Techno” was. This one is all staccato minimalism, keys and whichever random non-musical samples the cocaine in Kanye’s brain told him to toss in there, with a completely unnecessary coda that finds Yeezy elbow-dropping the sub-bass button for damn near a minute. It was also probably the last time Jay was able to flow over something so futuristic and not come across as “How do you do, fellow kids?” style, yet he still felt like he needed to throw in a couple bars gesturing to how him being a billionaire is politically progressive, which Kanye quickly offsets by rapping about getting his dick sucked in a bathroom. If these guys weren’t on the same page, that’s fine, this is also a song that prominently features dialogue from the Will Ferrell/Napoleon Dynamite guy ice skating comedy Blades of Glory, which may have only been seen by Kanye when it first came out. It’s no “Otis,” but this song was a moment, countless memes to come embedded within it, and if Jay wasn’t 100 percent in on the joke, well, that was his role and he played it perfectly. —DREW MILLARD

78. Regrets
prod. Peter Panic
Reasonable Doubt [1996]

Jay-Z can seem cold and overly calculating—a billion dollars doesn’t come from being sentimental. But on the closing song from Reasonable Doubt, we hear him more pensive than ever before or since, yearning for a real life that isn’t measured in delusional rivals and night-time police raids. The first verse is a screed of his own bad deeds, a countenance of villainous behavior. He has never sounded more unguarded, even using a racial slur that’s shocking to hear now that he’s become a friend of Presidents and Prime Ministers. The second verse is an apology to his mother. Yet, it’s the third—one of my favorites of his career—that embodies the soul underneath the mystique. The veneer of respectability comes off when talking to the soul of a departed hustler that he looked up to (“When he was here, he was crazy nice with his, son”), claiming that a mutual friend of theirs is annoying Jay so much that he’s going to send him a roommate in hell. Before too long, though, he composes himself: “I’ve been talkin’ to your spirit a little too much.” And just like that, he’s gone. —JAYSON BUFORD

77. Ignorant Shit f/ Beanie Sigel
prod. Just Blaze
American Gangster [2007]

Even in Roc-A-Fella’s final years, as their collaborations grew less frequent, Jay and Beanie were always a perfect match. If Jay was the don, Beans was his most trusted capo. On “Ignorant Shit,” Just Blaze brilliantly reworks The Isley Brothers’s “Between the Sheets”—the same sample used to convey languid luxury on “Big Poppa”—in a way that suggests, counter to its original form and prior repurposings, confrontation and urgency.

The track doesn’t contain Jay’s best double entendres, and his defense of Kingdom Come on the intro feels even sillier two decades out, but “Ignorant Shit” is a testament to the power of great delivery. Bragging about hustling since CHiPS was on doesn’t make Jay sound like an old fogey, but a distinguished veteran. The uncharacteristically blunt threats of violence on the second verse feel real because you can hear the loathing in his voice. The same is true for Beanie, who dubs himself “the ‘07 Ice Cube.”

Does “Ignorant Shit” have tight internal logic or individually iconic bars? Not really, but it’s a great song from Jay and one of his most gifted proteges. It’s a record so good even Mixtape Lil Wayne couldn’t make the beat his own. —GRANT RINDNER

76. Bring It On f/ Big Jaz and Sauce Money
prod. DJ Premier
Reasonable Doubt [1996]

The least discussed Primo track on Reasonable Doubt; the one with the Fat Joe sample and mournful horns, where Big Jaz says “Fahrvergnügen.” Jay comes in on the word “mannerisms” and it’s almost suspenseful, opening the verse in that way: what is this word coming out of his mouth and where will the line go? He stutter-steps all over the place, taking unexpected pauses that culminate in his memorable pronouncement: “I am…two-point-two pounds.” The human kilogram is talking and wouldn’t expect any of us to understand this money—a recurring theme in his art and life. —ROSS SCARANO

75. American Dreamin’
prod. P. Diddy, Sean CLV, and Mario Winans
American Gangster [2007]

Jay handles a Marvin Gaye sample like the wheel of an S-Class Mercedes, capturing the sentiments of strivers everywhere. Opening with innocent, stoned dreams of glitz and glamor, the song takes on a cinematic narrative of its own, as Jay Christmas Carols us through getting into the drug game, moving up the ranks, and finally touching the success you craved, only to wind up in the back of a squad car. Anyone who thought Jay’s skills had atrophied for good after the mature-rap misfire of Kingdom Come only needed to hear the first three tracks of American Gangster to know that all he needed was the right muse. —GRANT RINDNER

74. 7 Minute Freestyle w/ Big L
prod. Mufi [Miilkbone’s “Keep It Real”]
From “The Stretch & Bobbito Show [1995]

Before his murder in 1999, the on-record persona Lamont “Big L” Coleman crafted confessed to crimes against humanity in such diabolically vivid detail that his only literary opponent was Stephen King. That was until L brought “the guy who ran with Kane and Jaz-O” to the sacred backpacker proving ground, The Stretch Armstrong & Bobitto Show. For the next seven minutes, L unleashed bars of hellfire and brimstone, freestyled and pre-recorded, while Jay used his air time to manipulate pockets at will. The clash of untapped titans was dubbed to cassette and bootlegged across the globe, lo-fi hiss and all, but wouldn't be appreciated by one of its creators for decades. “We were just happy to be on the radio.” —ANTHONY SEAMAN

73. Grammy Family Freestyle
prod. Kanye West, co-prod. Jon Brion [DJ Khaled’s “Grammy Family”]
From “The Funkmaster Flex Show” [2006]

Where the “Poppin’ Tags” beat is the apotheosis of Kanye West’s early production style, “Grammy Family” is the evolution: urgent, paranoid, would plausibly be at home on the era-defining LP he’d finish nearly five years after the fact. And still, Jay’s freestyle over it on Flex’s show (repurposed in a few different forms on subsequent mixtapes, never to the same effect) renders it mere scaffolding. In a career full of it, this piece is perhaps the most persuasive bit of self-mythologizing, precisely because it treats, on a syntactical level, the canonization as arbitrary, tenuous, human. The peers are ghosts and the IPOs are just rumors. —PAUL THOMPSON

72. In My Lifetime (Remix)
prod. Big Jaz
single [1994]

Camus said that the meaning of life is whatever keeps you from killing yourself. On the glitzy and motivational “In My Lifetime (Remix)” Jay-Z seems to derive that meaning from embracing groupies, firing off rounds from a black Mac-10, and sporting diamond-cut gold in the Tunnel. And when he raps “Is it just a mirage, all these girls? Is this world, my world?” in a skippy flow, it sounds like he’s genuinely pinching himself; consequently, the bars carry a refreshing humility, far from the Picassos that would come later. —THOMAS HOBBS

71. Show You How
prod. Just Blaze
The Blueprint 2: The Gift & The Curse [2002]

Speaking chronologically, this is the last time Jay betrayed such utter contempt on record—for those who drive BMWs instead of passing them to baby mothers, rap about the watches they hope to get, “eat off per diem on the low like a caesar,” sure, but most of all for Diesel Jeans. —PAUL THOMPSON

70. I Just Wanna Love U (Give It 2 Me)
prod. The Neptunes
The Dynasty: Roc La Familia [2000]

At the dawn of the millennium, Jay-Z was unparalleled in his ability to shape where hip-hop would go next, identifying rising producers and turning them into superstars. By the time he linked up with The Neptunes, they’d already helped NORE, Ol’ Dirty Bastard, and Mystikal transition from grimy to shiny. But it’s “I Just Wanna Love U (Give It 2 Me)” that turned the duo into pop’s hottest producers. It almost didn’t happen: Jay had planned to use “Parking Lot Pimpin’” as the lead single for the Dynasty album, but after a last-minute studio session with Chad and Pharrell, he scrapped those plans, pivoting the rollout to showcase their clipped guitars, shuffling drums, and falsetto hooks. The result? One of Jay’s sweatiest club bangers, kicking off an incredible early run of Neptunes classics. —SON RAW

69. Dear Summer
prod. Just Blaze
Memphis Bleek’s 534 [2005]

This elegiac, post-“retirement” letter to the rap game fits so perfectly over Just Blaze’s chipmunk sound that it’s easy to forget “Dear Summer” never started there. New York first heard these bars in a Hot 97 freestyle, accompanied by extra disses and Funk Flex bombs, before Blaze pushed Jay to put it on wax. Sure, El Presidente already sounded like a tired veteran (“I ain't none of these half-assed newcomers”), but there was still a hunger, that broiling desire to show and prove (“You gon’ make that boy Hov put your name in a song/If you that hungry for fame, motherfucker, c'mon”). In retrospect, Shawn Carter could never have left it all behind for corporate America; he was too spiteful, too competitive, too eager to steal the show. But if “Dear Summer” had indeed been his coda, his legacy would have stayed assured. —NITISH PAHWA

68. Jigga My N——
prod. Swizz Beatz
Vol. 3... Life and Times of S. Carter [1999]

In 1998, DMX changed New York’s temperature, depicting the streets without glamour or sentiment. Caravaggio by way of Yonkers. Jay-Z asked Ruff Ryders bosses Waah and Dee for Dame Grease, who produced much of X’s debut. They sent over their nephew instead. Jay initially balked at working with young Kasseem, who produced as Swizz Beatz, but their session yielded a suite of songs including “Jigga My N——,” a muscular anthem unique to late 90s New York where Jay briefly entered the Ruff Ryders universe, allowing us to imagine an alternate reality where he leads a phalanx of ATVs and motorbikes down the Bruckner Expressway. —EVAN NABAVIAN

67. 4:44
prod. No I.D.
4:44 [2017]

The howled, yearning anguish of the vocal sample, chopped into stuttering uncertainty by No I.D., carries the principal sorrow of “4:44.” UK vocalist Hannah Williams’s looped mourning—fittingly also embodying a cheater’s regret—is a pure distillation, whereas Jay’s bars are couched in caveats and shrunken defense. Raps about guilty ménages à trois, missing out on vacations, and how it took his children’s birth to “understand” women show the limited depth of Jay’s soul-searching, though fortunately, vulnerability carries the majority of the lyrics. The desperation of his pre-mogul lifetime still fuels his lamentation. Poetry blooms in the sidewalk cracks of his typical bravado, making a startling switch off autopilot on 4:44 and “4:44.” —ALY ELEANOR

66. Only a Customer
prod. Irv Gotti
Streets Is Watching OST [1998]

One imagines this was deemed a little too glittery for the studio albums, a relic of the days when Jay, Dame, and Biggs were trying to get “In My Lifetime” to pop. But the lushness makes Jay sound younger, all while he’s getting all wizened and promising to shoot through the city “like a rumor.” Ironically, is there a more specific way to refer to a Lexus’s paint job than “grayish bluish”? —PAUL THOMPSON

65. Reservoir Dogs f/ The LOX, Beanie Sigel, and Sauce Money
prod. Erick Sermon, co-prod. Rockwilder and Darold “Pop” Trotter
Vol. 2... Hard Knock Life [1998]

I mean, the polo shirt is right there on the cover: Jay’s whole thing was being unbothered. But “Reservoir Dogs” is unique in that it finds Jay the most animated, staccato rapper on the track—an effect best captured in the headfake “Locked in the slammer? Nope, popped up in Atlanta,” where the little hesitations do not quite add up to a measure-long syncopation, but still have the effect of making each detail feel like a discrete aside. Smooth and delightfully jagged at once. —PAUL THOMPSON

64. Who You Wit II
prod. Ski
In My Lifetime, Vol. 1 [1997]

Two years later, the Waffle House reference on “Do It Again” would retroactively make the handwave dismissal of Denny’s here seem like Logan Roy bit of corporate maneuvering. What a joy to see America’s business minds at work. —PAUL THOMPSON

63. La-La-La (Excuse Me Again)
prod. The Neptunes
Blueprint 2.1 [2003]

Before Justin Timberlake made your ears bleed in the name of Trolls, before every C-quality movie assembled a grab bag of C-list rappers for forgettable posse cuts, we used to get songs like this on movie soundtracks. And goddamn was Bad Boys II lucky: flowing effortlessly in the pocket over one of the Neptunes’ greatest beats (fight me), Jay channels Mike Lowery’s Miami in its cigar smoking, money flaunting, bottle popping, jet skiing glory, while also managing to riff off Big Daddy Kane. The main event—The Black Album—arrived seven months later. Luckily he already had music for the afterparty. —JACKSON HOWARD

62. 99 Problems
prod. Rick Rubin
The Black Album [2003]

There’s a well-documented phenomenon where, as musicians age, many of them drift toward the styles that were popular in their formative years. So for what was marketed as his final music video (complete with a bullet-riddled corpse that gets qualified by a PSA at the clip’s end from an unharmed star), it’s fitting that Jay got a little Reaganish. The sparring with his critics over how he particularly and Black artists generally are read in bad faith, which began in earnest on “Money, Cash, Hoes” and continued through “Come and Get Me,” “Renegade,” and so on, bookends “99 Problems.” But the song is really a vehicle for its second verse, where Jay voices (like Biggie on “Warning”) both sides of a conversation between himself and the cop who pulled him over. The 4th Amendment gets waved around like a bottle of Cris. —PAUL THOMPSON

61. Brooklyn’s Finest f/ The Notorious B.I.G.
prod. Clark Kent, co-prod. Dame Dash
Reasonable Doubt [1996]

Forget, for a moment, the long-raging debates over Jay-Z’s penchant for reusing Biggie’s bars; forget, if you can, the fallout from the infamous “two … Pacs?” quip; forget, even, about Puff’s forced presence. Take a few minutes, instead, to bask in the joy and glory of “Brooklyn’s Finest,” an accidental meeting of the two MCs who could lay claim to that title, a friendly toe-to-toe escalated to ecstasy over the Ohio Players’ rambunctious pianos. B.I.G. still runs away with it, his malicious, delicious flow conveying the most vivid mob cosplay you’ve ever heard (“The M.A.F.I.A. keep cannons in they Marc Buchanans!”). Yet Jay still holds his own, riding off his compadre to run up and stunt silly while assuming the hustler image he’d sport all the way to superstardom. —NITISH PAHWA

60. People Talking
prod. Ski
Jay-Z: Unplugged [2001]

There’s a conflation, here on the lone studio track hidden at the end of Jay’s superb live album, between poise and fatigue. The song’s magic trick is that from line to line, it’s never quite clear which he’s trying to project and which is creeping out from under the surface. —PAUL THOMPSON

59. What We Do
prod. Just Blaze
Freeway’s Philadelphia Freeway [2003]

Memphis Bleek might have been the rapper who Jay had planned on handing the dynasty to once he hung it up, but Beanie Sigel ended up being the guy who did the most to keep the Roc alive as more than a Jay-Z vanity label, both through his excellent albums The Truth and The Reason as well as through forging a Philly-to-the-Roc pipeline that would give us the mighty, mighty State Property and its associated members/sub-groups (this is not the time to litigate the Young Chris flow allegations). By the late ‘90s, Jay might have been sitting atop the mountain and a full-on commercial juggernaut who could sleepwalk his way through pop hits if he’d wanted to, but one can only assume that having a crew of scrappy, hungry Philly kids nipping at his heels gave him reason to keep his sword razor-sharp, not only for personal pride but to justify the brand of rap he was releasing under his imprimatur. The finest example of the Roc-A-Fella/Philly connection comes on Freeway’s “What We Do,” which unites Free, Beans, and Jay with an urgent, beatific Just Blaze beat that makes everything sound frantic and bittersweet. Though Freeway takes the song with the verse of his life, Jay comes away with the best line on the track with, “Gotta kill witnesses because Free’s beard’s stickin’ out.” Thus began a chain of events which led to Eminem rapping about hiding in Freeway’s beard and then Freeway sampling that line and making an entire song about his beard. This, we can all agree, is the God MC’s ultimate legacy. —DREW MILLARD

58. Murder to Excellence
prod. Swizz Beatz and S1
Watch the Throne [2011]

If Watch the Throne is but a gold-plated monument to rap’s two biggest egos, then we might consider “Murder to Excellence” a posse cut for its inclusion of the superego and id. To describe the conceptual cut as among Jay-Z’s most overtly political songs is not to suggest that its politics are coherent as much as it is to say that they are his. Consider “Murder to Excellence” a sort of ideological roadmap charting the course of the mind that birthed Reasonable Doubt as it transformed into the one responsible for “The Story of O.J.” And yet, at the risk of sacrificing evenhandedness: it is hard, upon hearing Fred Hampton’s self-appointed successor espouse a Black excellence not of free lunches but of Maybachs, to shake the sense that the FBI won. —OCK SPORTELLO

57. My 1st Song
prod. Aqua and Joe “3H” Weinberger
The Black Album [2003]

In conception and in naming, “My 1st Song” is overdetermined and on-the-nose: it’s the last song on his last album (get it?) and tells the story of Jay’s life in the rapid fire flow of his early years. Yet the obvious scaffolding of The Black Album’s closing track never gets in the way of the magic. As much as we see Jay’s wheels turning, “My 1st Song” is far more than the sum of its parts. The determination, the careful swagger, the gratitude: it’s all here, over a wistful guitar sample from the 1960s Chilean band Los Angeles Negros (“My 1st Song” is the only track produced by a previously known producer on the album, in this case Nicholas “Aqua” McCarrrell), Jay comes to terms with “second major breakup” of his life. The cherry on top is the outro, where Jay sounds earnestly unburdened, and thanks everyone who helped along the way. —JACKSON HOWARD

56. Otis
prod. Kanye West
Watch the Throne [2011]

Hidden a little deeper into the comment section of the official music video for “Otis” on YouTube is my favorite line from Funkmaster Flex’s infamous premiere rant: “THEIR MONEY IS YOUR MONEY AS OF RIGHT NOW.” What tickles me every time I hear that part of the rant, one uttered in a fit of euphoria and excitement, is how much Jay and Kanye would categorically disagree with that notion (at least out of context). In the museum of Watch The Throne, one filled with various opulent and gaudy displays of musicality, the piece adorned with Otis Redding’s wails and bounding organ crashes is among its most stunning. Everything that the old friends boasted about felt purposely unattainable, delivered with an air of certainty that you would never reach their levels. Yet when Jay momentarily lowers the intensity of his first verse to muse about rolling through the city with his arm out the window, you’re flooded with the foolish belief that you can do this too— a sliver of a Jay’s old allure that was becoming a faded memory. —MATTHEW RITCHIE

55. One Minute Man (Remix)
prod. Timbaland, co-prod. Big Hank and Missy Elliott
Missy Elliott’s Miss E... So Addictive [2001]

It’s not the version you think of, but it’s the one you need. —ANDREA DOMANICK

54. Marcy Me
prod. No I.D.
4:44 [2017]

On his 13th studio album, Hov auto-crucified, finally shedding his impenetrable, bulletproof persona, as exemplified on the opening track “Kill Jay-Z.” He emerged simply as Shawn Carter, presenting a figure as close to an everyman as a billionaire hip-hop legend can attempt to be. “Marcy Me” is an extension of that ethos, reflecting on the days before Jay and the Marcy projects that a young hustler once called home. He pays attention to the man behind the curtain, and is better for it.—DJ SHORT

53. Hey Papi f/ Amil and Memphis Bleek
prod. Timbaland
Nutty Professor II: The Klumps OST [2000]

En route to undercut Sherman Klump’s nine-figure youth serum sale, Buddy Love exits a cab playing “Hey Papi” as he leaves a ten-cent tip. For the first half hour of The Nutty Professor II, Love’s id possesses Professor Klump at every attempt to be vulnerably triumphant while courting commitment.

It’s this same Iceberg Slim chauvinism Shawn Carter confronts on “Hey Papi,” the Timbaland-produced plea for forgiving a life of shrewd fuckboy behavior in favor of being the Jiggaman’s lone mami. It’s the epilogue to “Big Pimpin’,” perhaps a promise to Beyonce, and a key cog in one million soundtracks sold. Whether righting his own wrongs or writing from the perspectives of Foxy Brown, Bugs Bunny, or Buddy Love, Jay juggles characters with Eddie Murphy’s malleability. —IAN STONEBROOK

52. NYMP
prod. Rockwilder
Vol. 3... Life and Times of S. Carter [1999]

Throughout the first four albums, Jay-Z retraces his steps, returning to familiar names, places, ideas: “Can I Live,” “Coming of Age,” “Who You Wit,” the Too $hort features, Jaz-O before the beef. “NYMP” concludes a trilogy begun by “Where I’m From” and “You Must Love Me”, where the Marcy Projects loom as a breathing “ghost-like” spirit brought to life by the crack epidemic, a presence that warped and devoured your ambitions.

“You could smell it in the hallways,” he would tell Bob Simon in a 2002 interview with 60 Minutes. “You was doing it, or you was moving it.”

In the same segment, Simon dubbed him “the son of Marcy” bringing “hip-hop to the heartland,” a conduit for “white suburban teenagers getting jiggy wit it.” Before he went national, global, federal, political: Jay couldn't leave Marcy. —GUS TURNER

51. Guess Who’s Back
prod. Kanye West
Scarface’s The Fix [2002]

“Guess Who’s Back” is Scarface’s song, but really it’s a showcase of when Roc-A-Fella operated as rap’s pre-eminent perpetual motion machine. Jay shit-talks his way through the intro and delivers a scorching opening verse, Kanye does some brilliant manipulation of The Originals’ “Sunrise” and handles hook duty for the legends, and a young Beanie Sigel proves he can bring home a track with verses from two of hip-hop’s best.

Jay’s verse is a showcase of varied styles, from stupidly brilliant one-liners (“I’m on the block like I’m eight feet tall”) to emotional appeals (“You can blame my old earth/For the shit she instilled in me, still with me, pain plus work/Shit, she made me milk this game for all it’s worth”) to vivid visuals (“Came from the dirt /I emerged from it all without a stain on my shirt”). —GRANT RINDNER

50. Pressure
prod. Prolyfic
Lupe Fiasco’s Food & Liquor [2006]

They met in 2002 at the Peninsula Hotel. Before the mixtapes, the deals, Jay-Z just wanted to see if Lupe Fiasco could rap: “You’re nice,” he said. From there, Lupe briefly resided in Jay’s orbit: Free Gucci pants, AF1s, and S Dots—eventually, an offer for a $50,000 advance and a Roc-A-Fella deal. He declined, ultimately deciding to build 1st & 15th with Chilly, before industry tectonics pushed the three back together for a possible reunion at Atlantic.

Instead, L.A. Reid made Jay a Godfather offer at Def Jam. No hard feelings: Jay exec-produced Food & Liquor, even as a leak forced Lupe to revisit his material—ultimately to the benefit of "Pressure." Eventually, they sent the beat to Jay, who liked it, but offered one suggestion. Somewhere, between the free shoes, the de facto mentorship, Lupe must’ve forgotten: “Yo, man, you know I do hooks, too?” —GUS TURNER

49. Encore
prod. Kanye West
The Black Album [2003]

When Jay-Z raps near the end of his third lengthy verse on “Encore”—the early continuation of an effortless skill to wrap up his soliloquies in a neat bow without feeling trite or corny—that he’s in the midst of a victory lap before his eventual exit from the game, there’s a tinge devilish glee. At least a part of him clearly believed it, as though he can’t wait to grant himself a respite from the game. But the sigh at the beginning of the second verse, buoyed by a legion of trumpets that capture the vigor of a live marching band, before Jay spits, “Look what you made me do/Look what I made for you,” betrays his true urges. He knows that he can’t walk away. Not when it feels like immortality is within his grasp, with the crowd chanting his name after nimbly blistering through another 16 bars with ease: he might as well make them beg for more. —MATTHEW RITCHIE

48. It’s Like That f/ Kid Capri
prod. Kid Capri
Vol. 2... Hard Knock Life [1998]

For all the examples, throughout his catalog, of the outright sorrow Jay’s endured, few songs strike such a spiritual minor key as this one, furnished by the legendary DJ Kid Capri. Maybe it’s the way the substances (base for the fiends, chasers for Hennessy) are first presented as salves for an impossible world, then consumed as a show of force or abandon—as Pyrrhic a victory as you can score in front of bottle girls. —PAUL THOMPSON

47. Diamonds From Sierra Leone (Remix)
prod. Kanye West, Jon Brion, and Devo Springsteen
Kanye West’s Late Registration [2005]

No Jay guest verse wields the simple power of his presence like this one, released during the disintegration of Roc-A-Fella. With Dame Dash and Jay on the outs, the world wondered how the allegiances would shake out; as West parrots the public speculation on those events, a commanding voice interrupts him. “I got it from here, Ye, damn.” From there through “I’m not a businessman/I’m a business, man!,” Jay makes the obstacles in his past and present seem monumental, but his conquering them a mere fact of nature, like the sun rising. When he declared the Dynasty would weather the storm, it was as if it had never been in doubt in the first place. —JOSH SVETZ

46. Some How Some Way f/ Beanie Sigel and Scarface
prod. Just Blaze
The Blueprint 2: The Gift & The Curse [2002]

The superior sequel to “This Can’t Be Life” doesn’t have a superior Jay-Z performance, but every other aspect of the track one-ups the original. Beanie Sigel and Scarface’s verses are lights out, among their very best. Kanye’s insane beat, a sped-up sample of Jermaine Jackson’s “Castles of Sand,” is a sterling reminder of his pre-nitrous creative genius. And the song’s hopeful purview is a more natural posture for Jay-Z than the fabricated cynicism of his pre-Blueprint persona. Few cuts demonstrate the mastery of Roc-A-Fella’s peak as this one. —TAL ROSENBERG

45. U Don’t Know / U Don’t Know (Remix) f/ M.O.P.
prod. Just Blaze
The Blueprint [2001] / The Blueprint 2: The Gift & The Curse [2002]

Around the turn of the century, Just Blaze seemed to be in a space race all alone, competing with himself in an effort to break from orbit and alchemize old LPs into pure, uncut exultance. It would be unthinkable, from October 2001 to October 2002, that his beat for “U Don’t Know” would eventually seem tame—but when he gives himself room to let the sample breathe before it builds to its climax on the remix, the combustion is something to behold. Though M.O.P. would later denigrate Jay’s treatment of them at Roc-A-Fella (or at least compare him unfavorably to 50 Cent, who would also never get around to releasing an album of theirs), the creative synergy is undeniable, three rappers unshakeable at two different registers. —PAUL THOMPSON

44. Shiny Suit Theory
prod. Jay Electronica
Jay Electronica’s A Written Testimony [2020]

Released as a promotional and then on two different albums over a decade and a half, “Shiny Suit Theory” still sounds futuristic, a dispatch from a future where drums are passe and the notion of an America where even one Black artist could become an industry titan is once again mere fantasy. While the other Jay also rips off a near-career best verse (“We built a mighty high ladder, let me see you climb up”), Hov’s ventriloquizing of a therapist who says things like “Boy, you must be off your rocker if you think you’ll make it off the strip before they ‘Pac ya” is in many ways the thesis of his entire career. —PAUL THOMPSON

43. Song Cry
prod. Just Blaze
The Blueprint [2001]

The way that Bobby Glenn’s pitched-up voice opens the curtains, telling everyone that it really does “sound like a love song,” almost completes the trick of fully turning a player into a tender poet. The window dressing was certainly there, with Jay rapping over an especially sparse Just Blaze beat, fusing a driving drumbeat to sample’s falsetto runs. But what makes “Song Cry” more enthralling than a standard romantic deviation on The Blueprint—which exists almost as an endless stream of dominating bars from a self-assured titan—is the fact that it seems like Jay can never fully commit to the sensitive veneer he’s putting on. He oscillates between exasperated and contrite, rapping himself in circles trying to figure out where to place the blame for failed relationship after failed relationship. It’s a love letter born out of spite and frustration, smudged with teardrops, no matter how much Jay tries to convince us otherwise. —MATTHEW RITCHIE

42. It’s Hot (Some Like It Hot)
prod. Timbaland
Vol. 3… Life and Times of S. Carter [1999]

“WHAT THE FUCK IS 50 CENTS?” —PAUL THOMPSON

41. Public Service Announcement
prod. Just Blaze
The Black Album [2003]

Every person of a certain age—that is, any elder millennial politician or dweeb starting an email newsletter—has one: a post that says “ALLOW ME TO REINTRODUCE MYSELF,” tethered to an announcement that has since been forgotten. What the later memefication tends to lose about Jay’s original line is that this song is, actually, a great introduction. Here’s Jay-Z boiled down to his essence: he used to move snowflakes by the O-Z, he checks cheddar like a food inspector, he’s got the hottest chick in the game wearing his chain. Twenty years on, Jay may be better known for leaning into his Che Guevara with bling on side, but, as a wise man once said, you are who you are, player, and here he’s the guy who makes every bar iconic. —KYLE KRAMER

40. Izzo
prod. Kanye West
The Blueprint [2001]

The Jackson 5 sample is so obvious as to be itself a provocation. This single, which despite “This Can’t Be Life” a year earlier was the real cementing of Jay’s working relationship with Kanye, is still tethered to the Un Rivera case, a fact that seems wholly beside the point when Jay starts conjuring the smokers out back, selling their mothers’ sofas. To put Jay back on the analyst’s couch for a second, it’s fascinating to hear overcharging on behalf of the Cold Crush rationale for his business maneuvers—fair, beautifully punitive, and possibly true, but a justification nonetheless. Rarely does a pop hit have such athletic rapping or multidimensional writing; there are genuine dialectical tensions here. —PAUL THOMPSON

39. Poppin Tags f/ Killer Mike, Big Boi & Twista
prod. Kanye West
The Blueprint 2: The Gift & The Curse [2002]

“Poppin’ Tags” features Sleepy Brown, Twista, Killer Mike, and Big Boi over a classically soulful Kanye beat, but it doesn’t invite a “Renegade”esque debate. These are all natural collaborators and legends of their locales, the pinnacles of New York, Chicago, and Atlanta in 2002, unified by a hook that could define the era anywhere. Each lyricist is so charismatically distinct, it almost feels antiquated that they make such divergent stylistic choices over the same production. But it’s timeless, even if you forget it from time to time. —WILL HAGLE

38. Can’t Knock the Hustle f/ Mary J. Blige
prod. Knobody, co-prod. Sean Cane and Dahoud
Reasonable Doubt [1996]

Jay-Z and Dame Dash positioned “Can’t Knock the Hustle” as Jay’s introduction to the mainstream, dropping the track at the beginning of Reasonable Doubt and famously (and contentiously) wrangling legit R&B star Mary J. Blige for the chorus. The lyrics, full of double meanings and clever metaphors, exude bravado and strongman menace. But for someone trying to come off as a tough guy, “Can’t Knock the Hustle” sounds surprisingly wistful. That’s what makes it the perfect opening scene for Reasonable Doubt, an album all about a sensitive artist pretending he always wanted to lead a life of crime. —TAL ROSENBERG

37. Hova Song
prod. K-Rob
Vol. 3… Life and Times of S. Carter [1999]

Why Vol. 3 Jay is the coolest, in a couplet: “And I come with durags to your so-called awards /T-shirt with my chain out like fuck y’all all.” While the Knowles-Carter family has spent years simultaneously scolding and courting the mummifying voters of the Recording Academy, culminating in the preordained Album of the Year win for Cowboy Carter, there was once a time when a sneering dismissal was, correctly, all the time and energy Jay mustered for the proceedings.—ROSS SCARANO

36. Feelin’ It f/ Angela “Mecca” Scott
prod. Ski Beatz
Reasonable Doubt [1996]

Producer Ski Beatz holds Reasonable Doubt together, adding haunting samples and loops that make Jay’s debut sound contemplative. “Feelin’ It” hinges on filling a champagne flute, Jay playing with clean end rhymes and midline assonance—“rugged / crutches” for the former and “since diapers had nothing to live for like them lifers” for the latter. I’d argue that Jay’s straining to not sound strained, the sought-after blend of elegance and aspiration on “Feelin’ It” would be the key to his early career. Decades later, when Jay’s contemporary and fellow pop superstar Alicia Keys dropped the song’s piano intro on a video and smiled, we all were transported back in time to when Jay-Z sounded truly young. —EVAN MCGARVEY

35. Flux Capacitor
prod. Jay Electronica
Jay Electronica’s A Written Testimony [2020]

The esoteric, taster’s choice “Run This Town,” a quasi-posse cut with a disorienting beat and some of the best rapping Jay’s done all decade. It can be annoying when someone simply quotes lines from a song as evidence of its greatness, as if you haven’t listened yourself, but, like: “The slave that shook hands and humbled the duke of oil / The spook that spoke sterling silver and pearls twirled, tumbled out my nappy coils / Visions of sugar plums for all the boys and girls.” Jay fashions the rhyme out of the last word by resorting to an old-world Brooklyn accent, like he was just a knife-sharpener from some shtetl. —ROSS SCARANO

34. Can I Get A… f/ Ja Rul & Amil
prod. Irv Gotti & Lil Rob
Vol. 2… Hard Knock Life [1998]

Ah, 1998—those halcyon last days of a mainstream music industry blissfully unaware of the Napster maelstrom to come, when Carson Daly was the high priest of monoculture and Def Jam soundtracks to Chris Tucker-Jackie Chan buddy copy franchises were kingmakers. Such was the landscape that delivered “Can I Get A…,” the record that helped usher Jay from respected Brooklyn rapper to mainstream star. For Millennials and Gen Xs of a certain age, it was the first time a lot of people heard Jay Z, and almost certainly the first time most encountered an upstart MC then going by the name of JAH and the still-unsung prowess of Amil. Bouncy, synthetic, and just crude enough around the edges, the Irv Gotti and Lil’ Rob-produced track marked Jay’s first Top 20 hit as a lead artist and apparently his first song to make the TRL countdown, whetting pop’s collective palette for the forthcoming reign of “Hard Knock Life” and the Murder Inc. crossover formula that would rule much of the early ’00s. It’s not Jay’s best or deepest song—though there is something to be said for the proto-“No Scrubs” energy between him and Amil—but with its radio hook, collab chemistry, and major label luster, it captured the moment he figured out how to make street rap function as pop infrastructure. —ANDREA DOMANICK

33. A Week Ago f/ Too $hort
prod. J-Runnah
Vol. 2… Hard Knock Life [1998]

Vol. 2 is basically unconcerned with history: there are fewer autobiographical asides, almost no lifelines to bygone eras of rap. Save for “A Week Ago,” the sort of moral-instruction-on-immoral-subject that has been a cornerstone of hip-hop since its beginnings. The faux humility with which he compares himself to his unscrupulous ex-partner was, in 1998, his default tonal mode, and here it’s used to ice-cold ends. —PAUL THOMPSON

32. Allure
prod. The Neptunes
The Black Album [2003]

When a giddy Pharrell called up Jay-Z (captured in this documentary footage) he promised a new beat that would instantly make the rapper feel like the ending of Carlito’s Way. “It is like you are taking one last job before making it out!”

And few would disagree with this description of “Allure,” which remains the most cinematic moment of Jay-Z’s supposed swansong. Built around contrasting minor and major 7^th chords, which emit a warm, smoky elegance, the beat is a delicate little thing, with strings slicker than an orchestra conducted by Bernard Herrmann in the 1940s and gunshot percussion that sullies up the Neptunes’ groove. It all means you feel paranoid despite being paradise-bound.

From Jimmy Hoffa to James Dean, Jay-Z examines the shortcomings that plagued all of our most flawed American heroes, while making the distinction that he’s too many steps ahead to ever crumble like they did. “I’m living proof that crime do pay!” he beams. But the way Jay-Z later questions this trademark self-belief also results in a profound observation about the human condition that proves why the Brooklyn artist deserves all those songwriting awards. Maybe we’re all just “moths addicted to the floss.” Sounds about right to me. —THOMAS HOBBS

31. Come and Get Me
prod. Timbaland
Vol. 3… Life and Times of S. Carter [1999]

There’s a palpable difference between the music Jay released before and after his arrest for the stabbing of Lance “Un” Rivera at the Kit Kat Club (and his subsequent probation). There’s more weariness around violence, whether he’s invoking it as a tool or as a reporter would. But before “Chains is cool to cop but more important is lawyer fees,” there was “I got pride—I’m a nigga first/I got to cock back and pull the trigger first.” “Come and Get Me” is who Jay was pre-Un: a swaggering, dominant, former drug trafficker and gun-toter afraid he’s going to be a criminal forever. Over Timbaland’s funky yet-street Blaxtploitation beat—that is, before the switch into something futuristic; Timbaland was Jay’s greatest collaborator —he lays down bars about representing Black culture in the mainstream only to be hurt by all of the disrespect he gets in spite of it. Jay rarely sounds ahead of time: a testament to his emotional intelligence and business savvy, perhaps—but here, he sounds almost exactly like 2003 50 Cent, a startlingly paranoid dude out for justice and respect, not necessarily in that order. —JAYSON BUFORD

30. The Story of OJ
prod. No I.D.
4:44 [2017]

A late-career reflection and exemplar of Jay-Z as business, mannnnn. Backed by No I.D.’s gorgeous stitch-up of Nina Simone’s “Four Women,” and accompanied by one of Mark Romanek’s best music videos—a Bamboozled-like animated stroll through America’s ugliest racism—“The Story of OJ” is Mr. Carter’s pitch that his capitalist successes are also Black America’s. No, he won’t forget where he’s from, but he won’t pretend he isn’t a moneymaker at his core, or that he doesn’t believe accumulation is the best route to redistribution. In between therapy sessions over his whiffed DUMBO investment and hectoring, wince-worthy lectures on how Jewish Americans make investments instead of strip-club rain, Jay sounds astonishingly vulnerable and insistent in his self-made worldview: that joining the nouveau riche is, in itself, collective empowerment. Likely, you don’t find that too persuasive. But it’s hard to deny the man when his verbal challenges remain sharp as ever. (“Y’all on the gram holding money to your ear?/There’s a disconnect, we don’t call that money over here.”) —NITISH PAHWA

29. 1-900-Hustler f/ Beanie Sigel, Memphis Bleek & Freeway
prod. Bink!
The Dynasty: Roc La Familia [2000]

Jay’s verse ends with an invoice. For a grand total of 42 seconds of finessing consultation—one that, for what it’s worth, sketches out three distinct avenues to a come-up—our caller is billed for $800. Adjusting for inflation, that same audience would have cost our aspiring hustler $1,556 in 2026. Let’s say the average dinner runs two hours. Divide those 7,200 seconds by 42, and you establish the 2026 market rate for a two-hour sit-down with Hov at no less than $266,698. So, a suggestion of how you could finesse the age-old debate: take the $500k, spend roughly half of it on dinner, and use the rest to seed an empire. —OCK SPORTELLO

28. Politics As Usual
prod. Ski Beatz
Reasonable Doubt [1996]

Before he made any royalties from rapping into a microphone, Jay-Z’s money was profoundly unclean. Tales of wishing for mink coats, gambling on Tyson’s opponents, and leaving his family for the streets are all over “Politics As Usual,” where the lush Stylistics sample oozes and he explains not the core tenets of hustling, but its seemingly incidental details. Where other rappers are local, Jay here is national, likening himself to the real-life mafiosos. At times, Reasonable Doubt plays like Jay is splayed on a psychiatrist’s couch; this is when you nibble around the edges with a new therapist, still wondering if they’ll think you’re cool. —JAYSON BUFORD

27. Dirt Off Your Shoulder
prod. Timbaland
The Black Album [2003]

Though it became familiar through its initial ubiquity and seemingly endless half-life, this is one of Timbaland’s greatest beats precisely because it’s one of his most alien. That sounds so superficially abrasive could be harnessed into a pop format continues to defy physics; that too-clever lines like “52 cards went out—I’m through dealing now” could be made to sound so causal does, too. One of Jay’s great gifts as a vocalist is his ability to take the useful textures from bothered or hurried speech without ever actually being either of those things. Here, he scales and rappels down huge emotional cliffs without his heart rate changing a beat. —PAUL THOMPSON

26. Friend or Foe
prod. DJ Premier
Reasonable Doubt [1996]

A masterpiece of character writing from, canonically, rap’s greatest memoirist, “Friend or Foe” sees Jay use a top-notch DJ Premier blaxploitation setpiece for a downright Scorseseian monologue. In just over a minute and a half, he encounters an out-of-town dealer and points him back to Kansas with charisma and a dash of paternal resolve. But rather than the superhuman (over)confidence that guides the lion’s share of Jay-Z songs, the protagonist of “Friend or Foe” is anxious, jumpy, neurotic; speaking in a conversational, somewhat nervous tone which recalls Annie Hall more than Carlito’s Way. In addition to being an indicator of Jay’s strengths as a stylist, “Friend or Foe” strays pretty far afield from the Mythology of Hov while simultaneously fitting perfectly alongside his best work; a fascinating loose thread. —DOUGLAS MARTIN

25. Pump It Up (Freestyle)
prod. Just Blaze [Joe Budden’s “Pump It Up”]
The S. Carter Collection [2003]

For all its utility as journalism, its capacities for joy and menace, its serving as a canvas for brilliant writing in innumerable styles, and its ability to organize and galvanize toward revolutionary political ends, rap likes to remind you that sometimes all you need to do to operate at an elite level is think someone is a really terrible hang. —PAUL THOMPSON

24. Threat
prod. 9th Wonder & Jay-Z
The Black Album [2003]

“You came highly recommended by Ahmir.” It was Saturday, September 20, 2003—seven months after Little Brother’s debut, The Listening. Young Guru was a fan, but he wasn’t sure: Was 9th Wonder the guy, or was he just the guy in front of the real guy? After Questlove gave a good word, 9th found himself and his Justus League associate, Sean Don, auditioning for Guru, Memphis Bleek, and Jay-Z in Baseline Studios. He shuffled through 20-odd beats, then replayed a handful. Jay asked for the tape and told him to come back Monday.

“That was my shot,” he recalled. “It could’ve made me or broke me.”

On Monday, Jay handed him a blank CD. “A Woman’s Threat” was burned onto it. “See what you can do with it,” he said, before leaving the room. Just Blaze was in and out, Clark Kent, Freeway, Cedric the Entertainer. Twenty-five minutes went by. Jay came back, listened to the sample chop, and hit the booth to cut the ad-libs: “You n——s must got nine lives… 9th Wonder.” Sean Don shook his head in disbelief. 9th’s eyes widened. Years later, he remembered: It was the first time he’d ever seen a Roc-A-Fella chain up close. —GUS TURNER

23. Welcome to New York City
prod. Just Blaze
Cam’ron’s Come Home with Me [2002]

A story I swear I once watched Juelz Santana tell in an interview circa 2011, which I will not be fact-checking, goes as follows: Jay and Cam’ron had never recorded a song together, and considering Cam was on Roc-A-Fella at the time, this was a thing the streets needed rectified yesterday. However, Jay and Cam just didn’t get along: Dame Dash was the guy who brought Dipset into the fold, and Cam felt Jay didn’t give him the requisite resources or respect and left him in a position of having to do stuff like turning a closet in the Roc HQ into his office. So when it came time to cut a track together, Jay went in the booth and started doing his parts off top, like really leaning into it in a show-off kind of way, to the point that he even shouts out his “hand that don’t write” in the verses. In response, Cam—famously the most detached, unbothered guy in whichever room he’s in—got flustered at the thought of getting killed on his own shit and decided to try harder than he’d ever tried in his entire life, turning what was supposed to be an “Empire State of Mind” precursor where they listed a bunch of random crap about “New York City” into an exercise in passive-aggressive one-upsmanship, the pair going at each other using the patina of Concrete Jungle Wet Dream Tomato as cover. It’s not like they diss each other directly—though after Jay asks Cam if they’re both from New York City and Cam responds, “You’re damn right” his voice is positively dripping with sarcasm—as much as it sounds like they each know they’re the best rapper in New York City, and now that they’re recording with the only plausible competition, this is their chance to prove it. The whole thing got recorded at such a frenetic pace that Juelz, who was originally slated to rap on the third verse, never got a chance to do more than rap the chorus, and dear God are we lucky that Suno didn’t exist back then because Just Blaze absolutely would have AI’d some sample instead of singing the phrase “Welcome to New York City” himself. —DREW MILLARD

22. I Love the Dough
prod. Easy Mo Bee
The Notorious B.I.G.’s Life After Death [1997]

This would admittedly rank a bit higher on a list of the greatest Biggie songs, his final verse here being among the most perfect passages in a slew of them. But Jay acquits himself beautifully; the “place yourself in the shoes of two felons” hypothetical would become an organizing idea for the second two-thirds of his career. Bending the pronunciation of Mike Tyson’s name to fit that rhyme scheme should be such a hacky choice, but the swagger and gravity more than sells it—I guess that’s how you say it now, you think. —PAUL THOMPSON

21. Do It Again (Put Ya Hands Up) f/ Amil & Beanie Sigel
prod. Rockwilder
Vol. 3… Life and Times of S. Carter [1999]

The lead single from Vol. 3, Jay-Z’s most outward-facing album, “Do It Again” hits like a finale for the people and the persona he’d leave behind. How ancient does the idea of Shawn Carter starting a fight in the club feel? Jay’s verse is good—love the Big Daddy Kane references—but Beanie Sigel walks away with the song. Funny that for an artist whose career has been a study in perpetual Napoleonic self-crowning, Jay allowed himself to be one-upped on wax so often: Biggie on “I Love the Dough”; Scarface on “Guess Who’s Back”; Beanie here. Call it noblesse oblige for features. —EVAN MCGARVEY

20. N—— What N——Who f/ Big Jaz and Amil
prod. Timbaland
Vol. 2… Hard Knock Life [1998]

Hell of a way to end a partnership. Just before Jaz walked away from Roc-A-Fella, Jay-Z brought his mentor back for a sequel to “The Originators,” the goofy, sax-inflected tongue-twister that helped bring the now-ubiquitous triplet flow to hip-hop’s mainstream. “‘The Originators’ was the first song I was on,” Jay-Z wrote in the Vol. 2 liner notes. “We was using that fast style that everybody seems to be using now.” So here was a reminder, for their new audience, that Jay and Jaz weren’t just the first to do it—they were still the unrivaled best.

The duo’s last pre-beef collab remains an electrifying, intoxicating performance. Reshaped and restaged for Shawn Carter’s new image, the street corners and striped tees giving way to galactic club lights and shiny leather jackets, the near-30-year-old impresario raps and macks with a sharp sense of rhythm, crisp diction, and keen verbal dexterity that still wows the listener all these years later. (“So all I do is rap and sex, imagine how I stroke/ see how I was flowin’ on my last cassette?/Rapid-fire like I’m blastin’ a Tec, never jam though.”) After holding it down for three verses over Timbaland’s eclectic drums, Jigga then passes it off to Jaz, who adapts himself for the times: “You fly-by-nights stop chirpin’, b/Heavyweight’s light work for me/For the time, in this motherfucker ain’t nobody hurtin’ me.” For a bright, beautiful moment before their too-long feud, Jay and Jaz lorded over it all in a well-earned moment of triumph, throwin’ it back, switchin’ flows, and gettin’ dough.—NITISH PAHWA

19. Renegade f/ Eminem
prod. Eminem
The Blueprint [2001]

There are countless ways to illustrate the top-to-bottom excellence of The Blueprint, but among the most compelling: “Renegade,” Jay’s first collaboration with Eminem at a moment when the pair practically ran a duopoly over mainstream hip-hop, is a relative deep cut. On the surface, it’s a song clearly set up for Em to shine, with its focus on pearl-clutching critics and the two MCs’ status as lyrical iconoclasts.

And sure, Jay’s verses don’t have the uber personal charge of Eminem’s, but he’s also taking on a more challenging role, defending not just himself but rap on the whole. He makes an indisputable case for the vitality of the genre in a fractured nation, rapping “I bring you through the ghetto without ridin’ ‘round/Hidin’ down, duckin’ strays from frustrated youths stuck in they ways.” His flow is measured, but passionate, like a moving congressional testimony, making points that C. Dolores Tucker, Tipper Gore, and Ben Shapiro would struggle to refute.

“Renegade” found its way into the iconic Jay-Z and Nas beef, thanks to “Ether”’s potent “Eminem murdered you on your own shit” barb, but Jay had the harder job and handled it with grace and savvy, all while tackling a beat unlike anything he’d rapped on before. —GRANT RINDNER

18. Hard Knock Life (Ghetto Anthem)
prod. The 45 King
Vol. 2… Hard Knock Life [1998]

While we may never get to read Hov’s letter about a (fictional) seventh-grade trip to see Annie on Broadway, as detailed in his plea to the rightsholders that convinced them to clear the famous sample, we get to enjoy the 18-year runoff of his commercial breakthrough single. Rapping over showtunes wouldn’t faze anyone younger than Jay-Z (even if Big Daddy Kane and Method Man beat him to the idea of invoking musicals), but in 1998, the novelty could propel you onto the Hot 100. It’s amusing to imagine Jay looking in the mirror and recasting himself as the protagonist of an 1880s poem/‘20s cartoon strip/‘70s musical/‘80s movie—somehow it captured lightning in a bottle. The lyrics are refined and freewheeling, if not familiar, making an oddly compelling pair with a pitched-up Annie. “Musical theater rap” used to mean watching an ascendant Jay-Z skate over clomping pianos and children’s choirs; now, there’s Hamilton and Twenty One Pilots. —ALY ELEANOR

17. You Must Love Me
prod. Nashiem Myrick
In My Lifetime, Vol. 1 [1997]

At the start of his career, Jay-Z was propelled into stardom by songs that sublimated his traumas as both a victim and perpetuator of the crack epidemic into a slick yet world-weary bravado. In that context, the final track of his sophomore record can be understood as a much-needed bloodletting, the sort of confessional that permits an artist to exorcise the demons of one hustle in order to freely commit himself to a practice. “You Must Love Me” is neither Jay’s only song soaked in regret, nor is it his only explicit musical apology. But “You Must Love Me” is perhaps mischaracterized as a confessional. Where one expects to hear pleas for forgiveness—from his mother and the Mothers he served, from his brother Eric who he shot when he was twelve, from his ex he sent to smuggle cocaine on a flight—one instead finds a deeply felt meditation on the act of accepting forgiveness. Taken against a career of demands-in-titles’-clothing—“Come and Get Me,” “Do It Again,” “Change Clothes”—it’s easy to misread this one. “You Must Love Me” is an awestruck marvel, a mercy, the sort of revelation that grants the courage and grace to walk into the hospital room despite the circumstances under which you’ve been summoned. —OCK SPORTELLO

16. The Watcher 2 f/ Dr. Dre, Rakim, and Truth Hurts
prod. Dr. Dre & Scott Storch
The Blueprint 2: The Gift & The Curse [2002]

The Rakim feature is inspired, not only as a verse (though “My neighborhood is never sunny” and the closing pledge to “die with my eyes open” might make it his post-Eric B. best) but as a chess move, enlisting Nas’s idol at the height of that beef. But what elevated Jay’s extended opening turn here in my mind was seeing Kevin Gates rap bars from it so passionately. Jay is occasionally a victim of his own cool, the steady center of gravity underselling runs of impossible technical and linguistic imagination. But even the slightest bit of renewed scrutiny reveals someone animated by fury, indignation, and a memory that simply doesn’t flag. —PAUL THOMPSON

15. Intro (The Dynasty)
prod. Just Blaze
The Dynasty: Roc La Familia [2000]

This is, undoubtedly, one of the hardest beats of all time, even when stacked against Jay’s corpus of extremely hard-ass intros. For over a minute, he lets Just Blaze’s instrumental ride, peacocking like a fighter shadowboxing on his way to the ring, building anticipation for what will assuredly be a crazy first couplet to set up this, the opening of the most momentous of posse records, a line Jay thinks is going to blow people away so definitively that he even does a fake-out like he’s about to start rapping and then keeps chilling. WHAT ARE YOU GOING TO RAP FIRST, HOV? The answer, unfortunately, is “The theme song to The Sopranos/plays in the key of life on my mental piano.” This shit is a clunker, dude, made even worse because the theme song to The Sopranos, while iconic, is goofy as hell to imagine Jay rapping over, especially when we’ve spent over a minute imagining Jay rapping over that Kleeer flip, only to get, once again, “The theme song to The Sopranos /plays in the key of life on my mental piano.” Given this song’s prominent placement on this list, you can probably tell that these opening lines are more endearing than anything else, because you can really only go up from bars like that, and ascend he does, jerking the plane out of autopilot and doing lyrical barrel rolls just as he reaches cruising altitude. As he sets out dropping a verse thick with knotty, free-associative bars and references so canny they’d have sent listeners running to Wikipedia if it had existed in the year 2000, all is forgiven. By the time he’s dropped, “Trying to be calm but I’m gon’ get richer/through any means with that thing that Malcolm palmed in the picture/Never read the Qu’ran or Islamic scriptures/Only Psalms I read was on the arms of my n——s,” you’re so hooked in that you almost wonder if Jay starting out his raps by engendering negative goodwill was somehow a canny artistic choice, maybe even a metaphor for Jay-as-hustler’s ability to start at nothing and rise to glory. I mean, it definitely wasn’t, but such is the brilliance on display here—it makes you think that anything is possible. —DREW MILLARD

14. Heart of the City (Ain’t No Love) [Unplugged]
prod. Kanye West
Jay-Z: Unplugged[2001]

By the time “Heart of the City” dropped, Jay had already made the city and the rap game his. But with the crown came vultures and doubters, “young fucks spittin’ at me,” “sensitive thugs” who all need hugs, and a creeping sense of isolation and paranoia even within his hometown. The studio version of the song—the centerpiece of The Blueprint—is bitter in its recriminations as a way of self-protection; on a song that literally asks where the love is, Jay is nonetheless as guarded as ever. The live take, though, from his endlessly replayable MTV Unplugged album, lets the real feeling bleed through: the exhaustion and woundedness, the triumph and cheekiness and genuine soul searching.

When he raps “I told you ‘96 that I came to take this shit and I did!,” we hear his pride in the delivery; when he tells us that “I gotta buy bigger plates, and more baggies,” we smile alongside him as he holds in a giggle. But the x factor in “Heart of the City” isn’t Jay himself, but rather The Roots and Jaguar Wright, the latter of whom (before she became a conspiracy theorist and a recent joke between Jay and Questlove) takes things to church on the jaw-dropping final chorus the way Kanye likely intended when he produced the song originally for DMX. We feel the love, and we feel Jay feel the love. It’s transcendent. —JACKSON HOWARD

13. Streets Is Watching
prod. Ski Beatz
In My Lifetime, Vol. 1 [1997]

Diamonds, whether GIA-certified or made by setting open hands with palms out next to one another, could only be forged by surviving immense pressure. The last song B.I.G. ever heard from his dear friend Jay-Z was a distillation of Hov’s own survival, as a ghetto superstar and internationally recognizable come-up waiting to get got, “Streets Is Watching.” He’d play the record back five times, uninterrupted, awed by how Hov toed the line of dismissive and anxiously detailed. With repeated listens other nuances revealed themselves; the temperature motif corralling the second verse, how only a few words could describe an enemies desires and weaknesses, and the hook overlapping with the final bars of a verse serving as a reminder of proximity the anonymous “they” remains in waiting to pounce. With all eyes on you, will you crack or shine? —ANTHONY SEAMAN

12. D’Evils
prod. DJ Premier
Reasonable Doubt [1996]

About halfway through the greatest film about male friendship ever made, Mikey and Nicky have found themselves standing over Nicky’s mother’s tombstone in the middle of the Philadelphia night. There are signs that Nicky knows that his lifelong best friend is feeding information about his whereabouts to the jilted mob boss who wants him dead; either way, he’s feeling a melancholic nostalgia. “I think that’s the reason we’re such good friends,” Nicky posits, “because we remember each other from when we were kids. Things that happened when we were kids that no one else knows about but us. It’s in our heads! That’s how we know they really happened.” Mikey’s guilt curdles: “What are you talking about? I know what really happened when I was a kid.”

Great writing is the accumulation of a series of small decisions. One moment, the host of “D’Evils” stands on the precipice of manhood learning how to use a condom with his best friend; the next, he has the tear-streaked mother of that friend’s child kidnapped in order to kill him over a drug feud. With one verse on his first album, Jay-Z wrote the sort of story that others spend entire careers chasing: a tale of betrayal rendered authentically enough to support the cosmological theory of evil for which it stands. —OCK SPORTELLO

11. Takeover
prod. Kanye West
The Blueprint [2001]

We used to have to hold the lore in our brains. We either knew or didn’t know about the Summer Jam freestyle. We used to have to hear “The Takeover” on a CD. For months, we lived in a society where “Ether” wasn’t out yet, and this was. But now, it’s ubiquitous, totalizing: Prodigy is forgiven, but Jay-Z vs. Nas is eternal. In 2001 as now, the talking points: same. Every rap fan is liable to morph into Stephen A. Smith or Skip Bayless and defend one side or the other through fun yet fruitless rehashed arguments. It’s a debate that’s not really. Even Jay liked Illmatic. But the ratio: undeniable. Nas made hot lines, Jay made hot songs. I made a ranked list of 50 Jay-Z tracks, and I forgot “Poppin Tags.”

We’ve been told that beef is not what Jay said to Nas. It could just be a list of names who are running this rap shit. Jay was insultingly incisive on a personal level without explicating the messiest personal details. No hidden children, just you-know-who doing you-know-what with you-know-who, kept between the two alleged Kings of New York—and thus, per the times, the world. —WILL HAGLE

10. This Can’t Be Life f/ Beanie Sigel & Scarface
prod. Kanye West
The Dynasty: Roc La Familia [2000]

Aside from his excellent taste, Jay-Z’s greatest gift is his permeability. He can borrow from seemingly any style and voice in rap history. Here, on the anchor of The Dynasty: Roc La Familia, Jay grapples with loss on the most intimate levels.

While in the studio with Jay and Kanye and Beanie, readying himself to record his verse, Scarface heard about the death of a close friend’s child. He then submerged himself in the booth, transforming his song-closing verse into a meditation on God and pain and the self: “I could’ve rapped about my hard times on this song/But Heaven knows I would have been wrong.” His verse closes the song—nothing else could follow it.

Jay has the impossible task of opening the record. He chooses to offer his own pain: a stillborn child he’s forced himself to forget. He slows his cadence to the pace of a confession, matching the existential searching of ‘Face’s verse and the surprising anxiety of Beanie Sigel’s. The trio made two more classics together, “Guess Who’s Back” on Scarface’s The Fix and “Some How Some Way” on Jay’s Blueprint 2: The Gift and The Curse.

In 2000, Jay-Z was rap’s public face: If someone knew one rapper, it was Jay-Z. In the literary world in 2000, if someone knew one poet, it was Nobel winner Seamus Heaney, another artist whose craft moves along intersections of personal life and historical violence and myth. Heaney had just published his translation of Beowulf. Across that epic we encounter the old Anglo-Saxon word “thole,” which means to endure or to suffer. Heaney later wrote that that word became his way into the epic. On “This Can’t Be Life,” Jay-Z creates space for suffering in a way he’d never do again, letting us hear the burden underneath his own will-to-power: “Baby came out stillborn, still I gotta move on / Though my heart still torn.” —EVAN MCGARVEY

9. A Million and One Questions/Rhyme No More
prod. DJ Premier
In My Lifetime, Vol. 1 [1997]

A brief peek behind the curtain: When we solicited ballots for this list, a number of voters campaigned for the remix, which extends the beat from the “A Million and One Questions” portion of the song. Yet I’ve always been a proponent of “Rhyme No More”—not only for the contrast its legato brings to the hairpin turns on “Million,” but for its own hint of melancholy. The giant pendant Jay wore during the photoshoot for “Hawaiian Sophie” promotion was a statement, sure, and one Jay was certainly proud of at the time, but the way he invokes it here makes it sound more than a bit like an albatross. Even the comic image of Jay and his crew returning to a block they shot up to play Diana Ross from their car weighs heavily. Then there are the little idiosyncrasies, like the Satchel Paige hesitation when he says that he “picked the mailbox lock/’Cause I ain’t have/no key.” It’s sad, ecstatic, threatening, and self-deprecating at once; maybe it’s fitting that when the catalog was transferred to DSPs, they threw their hands up and called it “Medley.” —PAUL THOMPSON

8. Lucifer
prod. Kanye West
The Black Album [2003]

By 2003, Jay had proved himself over beats from virtually every crevice of rap; the few times he’d sounded out of place or out of sorts (the “Ha” remix, for instance) simply made him come back more fluid, more intricate, more protean than before. While “Lucifer” is not usually talked about as a virtuoso song—people more commonly cite the Kanye beat and the gripping and the materially chilling third verse—there is not a song Jay has made that is stuffed with more rhythmic ideas. Nearly every couplet is delivered differently than the last: with a new flourish, on a new part of the drums, in a new accent or syntax. It’s as if he needed to exorcise not only his demons, but his inspirations as well.

Which makes sense, because “Lucifer” sounds like the end of the world, “I gotta get my soul right” being very obviously a reaction to some ticking clock just out of frame. When he gets to that third verse—delivered as if he’s still half-asleep—Jay’s countering nightmares with a fantasy of his own, the eerily deliberate reversal of a real-world tragedy. And then, at the song’s very end, after all this spiritual reckoning, the tug-of-war between fear of God and fear for man, he essentially shrugs: take me or leave me. —PAUL THOMPSON

7. Imaginary Players
prod. Daven “Prestige” Vanderpool
In My Lifetime, Vol. 1 [1997]

Jay was playing in the face of the Fates when he tapped the Bad Boy mafia to co-produce his second album mere months after the passing of The Notorious B.I.G. But nobody listens to Hov for his modesty. Letting his hubris guide him would be repaid by taking two beats from a lesser known member of The Hitmen, Devan “Prestige” Vanderpool. On the one hand he’d be given a karmic punishment; “Sunshine” and its jiggy, yellow-suited buffoonery. On the other he’d be rewarded handsomely; “Imaginary Players,” a shit talking opus where that same ungovernable ego and penchant for disrespect ran amok.

Backdropped by “Imaginary Playmates” slowed to a haunting cruise, Jay unlocks infinite ways to make his opponent shrink to a crumb on the sidewalk, stealing their confidence while buffing his own. He’s the all seeing eye of the block yet your Hummer is nowhere to be found. You have money for a 12 pack while he could drop everything and go on vacation for 12 months. You couldn’t even spring for a manicurist on your flight? You might as well be in coach. His imagination knows no bounds and yet you being his equal is a laughing matter. Keep hustling playboy, that extra 30 grand will come along one of these days. —ANTHONY SEAMAN

6. Big Pimpin’ f/ UGK
prod. Timbaland
Vol. 3… Life and Times of S. Carter [1999]

The 2Pac picture did not approve. Pimp C was pretty sure about it. At each of his homes, the UGK rapper/producer hung a framed photo of his patron saint, occasionally turning to it for a séance during moments of self-doubt. In this case, it was hard for Chad Butler to imagine that the late Makaveli’s fuck-the-world revenant would endorse a collaboration with his erstwhile rival, “Jay-Z of Hawaiian Sophie fame.” And even if he did, he wouldn’t want him rapping over such a…“funny beat.”

Initially, no one wanted the most exotic slab of cybernetic funk that Timbaland ever stole from the souk. Built off an orchestral sample of luxurious late-‘50s Egyptian belly dance pop, the “Big Pimpin’” instrumental sounded like what ancient astronauts bumped while building the great pyramids of Giza. At first, even Jigga needed to be convinced that it should soundtrack their Superfly Goes Boating anthem. But he trusted Roc-A-Fella A&R Kyambo “Hip-Hop” Joshua,” who rightfully insisted that Timbo’s beat was a form of futuristic hieroglyphics that needed time to be precisely decoded.

When most people still thought that PAT was an SNL reference, Jay-Z was a massive UGK fan—even shouting them out in The Source cover story that dropped with Vol. 2 (the same quote also co-signed Sarah McLachlan and Jewel). The first Underground King signed on immediately. Shortly after hearing it, Bun B flew to New York, toured the Roc, and unleashed a hyper-technical 16 that doubled as the greatest pro-literacy advertisement in rap history. At conception, each rapper was supposed to have their own hook; but after Bun laid his down, everyone agreed that it couldn’t be topped.

Pimp C was a different challenge. Hov tried to enlist him for “A Week Ago,” but both sides refused to travel to record it in person. His second attempt didn’t fare better. Beyond the lingering feud with 2Pac—who Pimp C had never actually met—there was a misheard line about Jay-Z’s automotive sexploits. In Jonathan Abrams’s The Come Up, Hip-Hop recounted the confusion in full:

“Yo, I can’t be on a record with another man talking about playing with himself,” [Pimp C said]. I was like, “What you talking about, man?” He said, “This man is talking, playing with himself in the truck.” I’m like, “Nah, he says, ‘Let her play with it in the truck.’” He says, “Oh, okay, now that’s understandable. I understand that right there. So shit, I’ma check the record again and see what I can do.”

The Iceberg Slim themes may have been vintage UGK, but the beat was galaxies away from the riding-dirty soul that Pimp himself produced. For months, Bun kept trying to explain that this could be their commercial breakthrough, but that only made his partner more determined to throttle the idea. He didn’t want the group’s first mass impression to come via a Top 40 crossover track that theoretically could have been on The Mummy soundtrack. Eventually, Pimp agreed to do only 8 bars, provided that Big Gipp gave him his blessing to steal his “did it done it run it” mutant levitation flow.

A quarter-century later, it’s tempting to glimpse “Big Pimpin’” as manifest destiny. But this was the fourth single. It only became a hit because none of Volume 3’s previous punches landed, and at the apex of the pre-9/11 Fortune 500 rap era, the major labels still had a million bucks to throw to Hype Williams to commandeer a yacht and film at Carnival in Trinidad. And then after Pimp no-showed, they were willing to foot the bill for a second shoot in Miami—going so far as to ship Pimp’s brand-new Mercedes 600 to Florida because he insisted that it had to be pristine for the video. When he finally pulled up on set with Gloria Velez in tow, Pimp immediately went into a trailer, took off his shirt, and slipped on a mink coat. It was over 90 degrees and a bewildered Jay asked if he wasn’t going to get a little hot. To which Pimp uttered the best one-liner that Oscar Wilde never said: TV ain’t got no temperature.

The video is inseparable from the song. It is an opulent and over-indulgent masterpiece, an artifact of the time when the sun never set on the American expense account. No one has ever had more fun on a video shoot than Dame Dash, who eclipsed all previous levels of CEOs all in the video dancing. In its shameless misogyny, it’s a sibling to “Ain’t No Fun,” a document of its time, which both Jay and Dame later apologized for (in Decoded, Jay re-litigated the lyrics and himself asked “what kind of animal would say this thing.”)

But as far as the sonics, Jay glimpsed the future. If the “Ha” remix was popular but slightly awkward, this was the first immortal north-meets-south collaboration of the new century, foreshadowing not just the nascent rise of Atlanta, Miami, and Houston, but the globalization of hip-hop itself. If the word classic has become a tired cliché, this is the rare occasion where few other adjectives suffice. This is exactly what being young and alive in the year 2000 felt like. A triple-platinum certified track that you can now put on any night at any party all over the world, and everyone will know every word—even if they don’t speak English, let alone know what “buck” means. Afterwards, even the notoriously impossible-to-please Pimp had no regrets. It’s unclear what the ghost of 2Pac thought, but he probably would’ve loved it too. After all, this was the next millennium version of “I Get Around.” —JEFF WEISS

5. So Ghetto
prod. DJ Premier
Vol. 3… Life and Times of S. Carter [1999]

1999: It’s the night before Y2K, and Hov and his entourage walk out onto the TRL New Year’s Eve stage like they’re coming out of a clown car. Nobody knows what will happen when the clock strikes midnight, but there’s a clarifying effect to DJ Premier’s swaggering flip of Ennio Morricone’s piano keys and guitar plucks. Whatever the new millenium will bring, goes the announcement from Times Square to the televised world, Jay-Z will always be ghetto.

“So Ghetto” is a great Jay-Z song because it’s the sort of song that only Jay could make; it’s a coup that explains how Jay became king. What “So Ghetto” purports to say is that Jay-Z will not change himself to fit into popular culture; what it augurs is that he can bend popular culture to his whims. Consider: a sea of predominantly white hands and gelled heads of hair bobbing in transfixion, a pregnant pause, a shit-eating grin, the money shot. “Furthermore, ma! We tote guns to the Grammys, pop bottles on the White House lawn, I guess I’m just the same old Shawn.”

2016: It’s August 5^th, and Mr. and Mrs. Shawn Carter are at the White House to celebrate Barack Obama’s 55^th birthday. It’s not the first time they’ve been invited—nor, for that matter, is it the first time they’ve attended a White House birthday party, the 2011 iteration of which having been spitefully dubbed the “Hip Hop Barbecue.” Over the past eight years, Jay has become a sort of patron saint of what feels like a liberal Pax Americana brought about by the nation’s first Black president. What was once a nose-thumbing flex revealed itself as prophesy, and nobody knows that it’s about to end.

2026: It’s June 14^th, and the South Lawn of the White House has been transformed into a garish octagon. The nation, fittingly, has evidently elected to celebrate its two hundred and fiftieth birthday with a low-rent display of bloodsport. It is in this way alone that “So Ghetto” feels dated: the White House lawn has become, in the language of iconography, a place no longer worth despoiling. The attendant, month-long celebration includes a state fair too low rent for any rapper of note, to say nothing of Shawn Carter. The organizers settle for Flo Rida. —OCK SPORTELLO

4. Can I Live
prod. Irv Gotti
Reasonable Doubt [1996]

Irv Gotti pulled the car over in Manhattan so that Jay could hear the beat properly. What he’d done to Isaac Hayes was take apart the first couple minutes of “The Look of Love” in a bid for greatness: This song would epitomize the ambition, stress, and decadence of the Hustler; it couldn’t sound like anything else on Reasonable Doubt and it would be Gotti’s only placement on the album. He separated the atmospheric opening into two sections (one with the flute, one with flute plus the horn stabs); he grabbed the strings and rhythm section; and the climactic bit where the horns returned—that would be the chorus.

Much of Jay’s language comes back to vision and perception. Are you getting an eyeful? What can you really glean from four fiends away, his immaculate description of street distance? Picture Jay at the bar, laughing. He’s made it right? “Happy to be escapin’ poverty, however brief.” Rayful Edmond, the D.C. hustler name-checked in the first verse, dropped out of school to sell more drugs and his run lasted until he was but 24 years old. Valleys and peaks. Edmond got life and died in a halfway house at 60.

The lines are stacked with beautiful turns of phrase: “Convenient amnesia.” “I’d rather die enormous than live dormant.” And then a bit of deadpan restraint to cap off the first verse: “We can have a pleasant time, sipping margaritas.” No sense of life and death. A pleasant time.

In October 1995, the Hughes brothers epic follow-up to Menace II Society, Dead Presidents, entered theaters and there’s a scene where “The Look of Love” plays as three of the characters plot a robbery from the interior of a rolling black Continental. It’s seductive and utterly doomed. I’ve always wondered if Gotti got the idea for the sample watching the movie in some Manhattan movie theater. Gotti’s dead now, age 54, and no one can ask. —ROSS SCARANO

3. Never Change
prod. Kanye West
The Blueprint [2001]

No song captures the generational chemistry between Jay-Z and Kanye West better than “Never Change.” Built around the anguished baritone of David Ruffin’s “Common Man,” a soul staple about making peace with one’s working-class roots, it’s a document of the push and pull between old-school righteousness and concrete hustle cunning, where the latter ultimately wins out.

Jay’s China white raw reflections excavate one memory where he was robbed of nearly $100,000 worth of product—but had so much respect in the street, he was ultimately able to find a way to get it back. He name-checks old friends (Big Ran) who got locked up and so didn’t share in the Roc-A-Fella’ spoils. By referencing non-rappers never invoked before, it all feels unnervingly real, and like you’re privy to a handwritten letter between friends. All of this presents as autobiography, but the social comment is just under the surface. If former coke dealers from the Marcy Projects can become mini Warren Buffetts without rearranging their processes or philosophies, what does that say about America?

Beyond the Dickensian business juxtapositions, “Never Change” is extraordinary for all the new literary techniques Jay finds to describe scenarios that had calcified into genre conventions. Get paid becomes the money that’s untouched so long it starts to smell “moffy,” Don’t snitch gets embodied in the family dog, mute but endlessly loyal. He bleeds magic from the banal, maybe never as effectively as: “We all fish, better teach your folk/Give him money to eat, the next week he’s broke,” as if the fish Jesus found were really coded references to fishscale. —THOMAS HOBBS

2. Dead Presidents / Dead Presidents II
prod. Ski
single / Reasonable Doubt [1996]

As the saying goes, rap music is folk music, and is there anything in rap closer to establishing the legend of John Henry’s hammer than the two versions of “Dead Presidents”? Spending money from two presidential terms ago. The Lexus GS300, a symbol of being hood rich rather than formally rich (for reference: the Bentley Azure from the Vol. 2… Hard Knock Life cover, the repeated allusions to Maybachs). Drinking Cristal by the magnum, the first of a few trends Jay popularized only to kill years later (see also: throwback jerseys). The Nas vocal sample, serving as one of the bricks that built the greatest blockbuster rap battle of the 21st Century.

Lore is only a part of it. The bridge between the “Dead Presidents” single and its sequel—a Reasonable Doubt album cut that also got plenty of airplay—is one that reflects the duality of Jay-Z as an artist. On the former, over Ski’s pensive and haunting piano sample, Jay raps as though he still has one foot in the streets; for all we know, he might have. Although there’s plenty of boasting about being knee-deep in snow and running to the Diamond District, the looming threat of RICO trials and state’s witnesses linger in Jay’s thoughts. He enjoys the fruits of his labor, but as the song progresses, Jay frequently looks over his shoulder for snitches, shooters, and precinct stations.

To counter, the setbacks on “Dead Presidents II” are frontloaded: hospital visits, visions of the sidewalk dampening with quarts of his blood, the spiritual heft of killing a man. By the time the concept of divine intervention is introduced at the end of the first verse, Jay is already down in Vegas (or Reno, who actually knows?), drinking Mai Tais with Ty Ty. From there, it becomes a tour de force of Jay flaunts and taunts. Wannabe thugs ain’t got no plug like the famous MTV series, their bank accounts described as confetti, wearing iguana so fresh it might still be alive. And even with a prodigiously dexterous flow, he still has the mental acuity to be his own accountant.

Staking his entire career between the balance of embodying aspirational wealth beyond his wildest dreams and the nightmares he had to suffer in order to get there, the five verses split between the two versions of “Dead Presidents” puts up the first mile marker in Jay’s lifelong exploration between the spoils and pratfalls of a hustler’s life. To think, he gave away the core thesis of his most profound insights in his second-ever single: “I’m here to tell niggas it ain’t all swell/It’s heaven, then it’s hell, niggas.” —DOUGLAS MARTIN

1. Where I’m From
prod. Ron “Amen-Ra” Lawrence & Deric “D-Dot” Angelettie
In My Lifetime, Vol. 1 [1997]

“How real is this?” The first note of Amen-Ra’s titanic beat sounds like The Big Bang on wax, a fitting table setter for the tale of how rap’s greatest hustler came to be. Leave it to Jay-Z to start his most authentic song amidst a sea of real-life raps with a rhetorical question—this is the realest shit Jigga has ever written/

Up until this point, Jay-Z was something of a cipher: elite lyricist, gifted songwriter, nascent hitmaker, but ultimately shrouded in mystery give or take a “Regrets.” At the buzzer on his second album, that starts to change with one of the most self-lacerating, raw tracks he’d ever record but right before that, he sets the stage with a song explaining what kind of environment births such a person in the first place. And in the process, visions of home brought out the best in him.

Four four-and-a-half minutes, Jay stops flossing and starts explaining himself; in his hands a square mile becomes the center of the universe. You want autobiography? Here it is, as promised: no more finely-tailored mafioso three-piece suits, just a different, more crucial type of vest. Storytelling? Allow Jay to go full Act 1 Henry Hill, with bars that illuminate Marcy vividly enough to create your own Scorsese tracking shot in your head. Dizzying turns of phrase? Wrap your head around “Where the drugs czars evolve, and thugs are at odds/At each other’s throats for the love of foreign cars.” Niche drug-dealing details too specific to be fabricated? Enjoy Kevin Gates’s dissertation on the virtue of selling weight wet.

The quotables are endless: “A block away from Hell,” “praying to God so long that they atheist,” and of course “Where you can’t put your vest away/and say you’ll wear it tomorrow/Cause the day after we’ll be saying/”Damn, I was just with him yesterday.” Maybe it was it a sneak in 1997 to put himself in the mix of corner debates alongside Biggie and Nas, but after listening to this, it’s more like foreshadowing. Despite the dozens of bigger, wider-reaching, genuinely great songs elsewhere on this list, incidentally Jay-Z connected deepest, locked in the hardest, when he mentally went back to the blocks that for better or worse, put him up against the immeasurable odds he’d go on to conquer. How real is that? —FRAZIER THARPE