The 50 Greatest 2Pac Songs

Only God can judge this list

Art by Evan Solano

50. Changes
prod. Big D the Impossible, co-prod. Trackmasters
Greatest Hits [1998]

Around the time that Ronald Reagan took his last nap in a cabinet meeting, Martin Luther King’s widow wrote an admiring letter to Bruce Hornsby, a 32-year old, accordion-wielding, white Virginia soft rocker and future touring member of the Grateful Dead. His anti-racist piano meditation, “The Way It Is,” had so profoundly moved Coretta Scott King that she wanted to use it at the King Center for Nonviolent Social Change in Atlanta.

During Hornsby’s initial ascent, Tupac Shakur was a sensitive Baltimore art school kid who rapped as MC New York, and clandestinely memorized songs from Sineád O’ Connor, U2, and presumably the diviner of “Mandolin Rain.” Before his senior year, he reunited with his mother in the Bay Area, where he eventually joined Digital Underground and recorded his catalytic debut, 2Pacalypse Now. “Changes” was initially made for that album—the one that most explicitly reflects the Shakurs’ Black Panther roots.

In the same sessions that birthed “Brenda’s Got a Baby,” the producer Big D The Impossible flipped Hornsby’s ballad for Pac to indict police brutality, the crack epidemic, the killing of Huey Newton, endemic racism, mass incarceration, and one of America’s many limited skirmishes in the Middle East. It’s understandable why Interscope kept “Changes” off the final tracklist. In contrast to Pac’s finest early work, the storytelling is elementary, the hook sounds like a Subaru ad, and the scarcely chopped loop would have seemed unimaginative in a pre-Bad Boy era.

But after Pac’s death, his vaults were ransacked. Every adolescent poem, notebook sketch, and unreleased demo was dissected like the Dead Sea Scrolls—if Suge Knight had dangled the Essenes off a balcony for royalties.

“Changes” was among the first and biggest posthumous hits, the lead single from a 1998 Greatest Hits that turned Makaveli into an internationally worshipped dorm room deity a la Bob Marley. All it took was martyrdom, a wax-and-polish remix from Poke of the Trackmasters, and a refurbished chorus crooned by a low-level R. Kelly protégé. Right on cue, “Changes” became his “One Love,” his “Imagine,” his “One.” A sanitized universalist anthem made to be adopted by political “change” candidates. It places 2Pac in a lineage of proud radicals, but Hornsby himself even appreciated the added positivity that his original lacked. Instead of “some things will never change,” a slightly more hopeful Pac insists that “things will never be the same.”

In my own personal ordering of the “Best 2Pac Songs,” “Changes” probably wouldn’t crack the top hundred. But it’s emblematic of his atomic emotional power, and arguably the greatest heat check of all-time. What other artist could have a Frankensteined B-side—written and discarded when he was a teenager—become a Top 40 hit in 18 countries? It’s still the only posthumous song ever nominated for a Best Rap Solo Performance Grammy (where it lost to Eminem, of course).

A few years after “Changes,” Shock G appeared in a 2Pac documentary to casually offer one of the sharpest-ever dissections of rap cadences. He describes his own nasal tone, how Nas raps from the back of his throat, how Biggie swung like a jazz musician. Then he distills Pac’s intangibles:

When people say Pac is the best rapper of all time, they don’t just mean he’s the best rapper, They just mean what he had to say was most potent…the most relevant.

In the next breath, the erstwhile Humpty Hump shows just how much Pac stole from MLK: the move-mountains diaphragm boom, the Baptist preacher syllable accentuation, the gift for transforming simple language into a vessel for our loftiest aspirations. “Changes” was a first draft revealing a second coming about to arrive—who would soon be condemned to the same tragic fate as his predecessors.

We have no evidence that Coretta Scott King ever heard the improved version of Hornsby’s original before her 2006 death. But when the Vatican launched their official Myspace page in ’09, “Changes” was on the playlist—which is about as close to canonization as you can get. —JEFF WEISS

49. Only God Can Judge Me f/ Rappin 4-Tay
prod. Doug Rasheed & Harold Scrap Freddie
All Eyez on Me [1996]

“Only God Can Judge Me” is peak paranoid Pac; much of the song is him reflecting, in unnerving detail, on the 1994 Quad Studios shooting and the post-traumatic stress he suffered in its aftermath. As a vital signs monitor beeps in the background of his second verse, he recounts “the doctor standing over me, screaming I can make it,” and waking up “strangling, dangling my bedsheets.” It’s harrowing. But what makes “Only God Can Judge Me” special is that the song is anything but bleak, at least in how it sounds (and especially in comparison to the desperate vengefulness of Don Killuminati): the instrumental here is full-bodied and even groovy, with a roving electric bassline and a mosquito-in-your-ear G-funk synth. The real reason, though, that a song about PTSD and death sounds this smooth is because of Rappin’ 4-Tay, the Bay Area shit talker who slides onto the song’s third verse to provide Pac counsel and support with cool confidence (“Pac, I feel ya, keep servin’ it on the realer,” he begins). Once he does, it’s as if Pac snaps out of it: “Now I’m bout to floss some boss player shit with 4-Tay,” he finishes the song, almost certainly smiling. —JACKSON HOWARD

48. Do For Love f/ Eric Williams
prod. Soulshock & Karlin
R U Still Down? (Remember Me) [1997]

For nearly 30 years, Bobby Caldwell’s “What You Won’t Do for Love” has been frequently sampled or covered (like, 176 times) as uncannily vibey blue eyed soul. In the last 12 months, two popular Nigerian artists, Adekunle Gold and Seyi Vibes, took their stabs at it back-to-back. Back in 1994, when 2Pac recorded his own entry in this mini-canon, he was relatively late to the Bobby party, as roughly the tenth to sample the original—but his rendition was and remains one of the smoothest. Sought-after Danish pop and R&B producers Soulshock & Karlin made it so silken, in fact, it almost masks the bitter romance Pac describes in customarily vivid detail. Pac had a charming way of freeing himself from machismo when he wanted to, and here, he admittedly simps, falling hard for jealous, lying, women who reduce him to a side piece and cheat on him too. Thugz cry indeed. —MANKAPRR CONTEH

47. Runnin’ from tha Police f/ The Notorious B.I.G., Dramacydal, Stretch, and Lil’ Vicious
prod. Easy Mo Bee
One Million Strong [1995]

In the comment section of the video embedded above, one user has commented “Nothing beats this 1994 version.” About 1,300 people liked the post, but it’s followed by more than 40 replies debating not only the relative merits of the various “Runnin’” incarnations, but the exact provenance and logic of this one—whether it was actually cut in ‘93, if Pac’s verse had been edited for creative reasons or due to corporate pressure from a nervous Interscope. What we know for sure is that the record started out as an Easy Mo Bee-helmed cornerstone for whatever Pac would make after Strictly 4 My N.I.G.G.A.Z… For a time, that was to be his third solo album; Pac shifted focus to the first Thug Life tape, but the label apparently balked at such an expressly anti-police song during the heyday of congressional probes into hip-hop and other cultural products’ link to real-world violence. What’s lost in all this—and in the saccharine remix Eminem helmed years later, and even in the famous Tunnel freestyle, which is pitched as a competition between the two late legends—is the way Pac and Biggie’s styles complement and enhance one another, the former serrated, the latter fluid and syncopated, each convinced he’s the devil on the other’s shoulder. —PAUL THOMPSON

46. All Eyez on Me
prod. Johnny “J”
All Eyez on Me [1996]

As an artist, 2Pac was often praised for the forcefulness of his personality, his relatable expression of raw emotion, and the musicality of his delivery. But for many years, you rarely heard Pac celebrated as a pure emcee. Among hip-hop diehards—backpackers, mostly—2Pac was never on the same plane as Nas, Biggie, Andre 3000, or even pre-Blueprint Jay-Z. If it pleases the court, may I introduce as evidence the first verse from “All Eyez On Me”? Cruising through the starry guitar strumming of Linda Clifford’s “Never Gonna Stop,” Pac pulls out every trick in the book: mashing plosives together, internal rhymes, clever similes, rapid-fire delivery. All respect to Big Syke, but that first verse is why you keep returning to “All Eyez On Me,” the most powerful demonstration of 2Pac’s rapping prowess, living life as a boss player until the day he died. —TAL ROSENBERG

45. Gotta Get Mine
prod. Warren G, Colin Wolfe, and MC Breed
MC Breed’s The New Breed [1993]

From one angle, you could ignore the headliner entirely and consider “Gotta Get Mine” as one of the earliest instances of Pac trying out the type of gummy, slinking beats that Warren G models here, which would become more familiar to him as he spent more time living and recording in Los Angeles. But this is truly one of the foundational records for Michigan rap, embodying everything Detroit and Flint excel at to this day: vulpine cunning, breathless interplay, fluency in codes of all kinds. It’s the sort of things that jigsaws tidily enough into radio playlists without compromising either MC’s idiosyncrasies—one of the state’s chief exports. —PAUL THOMPSON

44. Against All Odds
prod. Hurt-M-Badd, co-prod. 2Pac
The Don Killuminati: The 7 Day Theory [1996]

Though released after his death—and succeeded by a whole cottage industry of posthumous records—the Makaveli album is generally understood to be the final document of Pac’s musical life. And its finale is perhaps the most frenzied point of his catalog. You could say he was aggrieved: there are the shots at Mobb Deep, Dre, various unnamed New York rappers, and the repeated undressings of Nas, whose style dismissed as 2Pac fan fiction (it’s amusing that both he and Big clearly felt this way at the same time). But the two specters hanging over the furious record are the ones Pac clearly held as his great enemies, Puff and Haitian Jack. It’s astonishing to hear what sounds like unfiltered contempt and rage delivered so virtuosically; the cadences are, on first listen, rendered invisible, but reveal themselves to be passages of almost impossible technical precision. And for as much as this sounds like a final bloodletting, five years before Jay pledged to “keep things between me and you for now,” Pac knows to leave just a little something unsaid. “You can tell the people you roll with whatever you want,” he hisses to Puff. “But you and I know what’s going on.” —PAUL THOMPSON

43. Old School
prod. Soulshock, Jay-B, and Ezi Cut
Me Against the World [1995]

The last year-plus of Pac’s life was colored by the feud with Big and Puff, which was generalized (by the press, but also by the participants) as a war between America’s coasts. That, combined with Pac’s well-known love for his adopted home state, reduced in the minds of many his New York roots to a biographical quirk, a point of trivia. “Old School” reveals Pac’s birthplace to be an essential part of his being. It goes well beyond the litany of rappers which opens the song: we flash on images of young Tupac—well, “MC New York” as he wanted to be known—freestyling on the train, playing on cramped streets with neighborhood kids, fleeing the transit cops with a can of spray paint in his hand. The most endearing part of the track actually comes after the rapping is finished, when Pac starts rattling off memories of how Brooklynites would make their presence known at house parties, how stickball games had to be broken up for passing cars, the way the Italian Ices tasted on hot summer days. His voice speeds up, as if he needs to commit all of this to tape before it floats away. —PAUL THOMPSON

42. Reincarnation f/ Lemika, Kastro, E.D.I. Mean, and Hussein Fatal
prod. Johnny “J”
unreleased

Over a misleadingly patient bit of Johnny “J” swing, Pac frets about the shadow lives of his core beliefs. “Many promises broken,” he raps, “as if it’s useless to hope.” For once smoking weed is conceded as a vice; the friends he raps about so lovingly, and so defensively, don’t know him, and his beloved California is only mentioned in an aside about how these cops in particular want him bloodied or killed. That he expects, upon his death, to be “a mystery to many, but a legend to some” is delivered in an eerily dispassionate number—Pac saves his ruefulness for the following line: “I’ve been a man for many women, but husband for none,” the unencumbered scamp from “I Get Around” rendered lonely, unneeded. What this opening verse actually is is a skeleton key, made to unlock in the Pac obsessive’s mind the nagging fears that underlie even his most swaggering late-period songs. —PAUL THOMPSON

41. Thug Luv
prod. DJ U-Neek
Bone Thugs-N-Harmony’s The Art of War [1997]

Few rap trivia points strike an eerier note: Bone Thugs-N-Harmony worked with both 2Pac and Biggie near the very end of their respective lives, and stood alone as the only group to collaborate with those two and Eazy-E the genre’s first three marquee losses.

And despite revisionist takes, no rap group loomed larger in the ’90s. Bone dominated—culturally and commercially. Coming off the success of “Notorious Thugs,” their showstopper on Life After Death, the Clevelanders’ momentum was at its peak when a posthumous 2Pac collaboration was announced for their third album, The Art of War. The record became a key selling point for a group already riding the number-one hit “Tha Crossroads” and the four-times-platinum E. 1999 Eternal. “Thug Luv” delivered, and while it didn’t quite match the impact of “Notorious Thugs,” it helped push The Art of War to four million copies and secured its place in the canon.

But the backstory is even better. Years later, it emerged that “Thug Luv” began as a Bizzy Bone solo track. In summer ’96, with both Bizzy and Pac at their respective peaks, fellow Ruthless artist Sylk-E-Fyne (of “Romeo & Juliet” fame) helped spark the collaboration. By the time it dropped, her verse was gone—replaced by the full group. Now, thanks to time—and YouTube—the original version finally tells the whole story. —ANDREW BARBER

40. Starin’ Through My Rearview f/ Outlawz
prod. 2Pac, co-prod. Hurt-M-Badd
Gang Related — The Soundtrack [1997]

One of Pac’s greatest talents was his ability to project unshakeable confidence and extreme vulnerability in the same song, highlighting both the uncertainty inherent in street life and the high of escaping its clutches. Likely owing to the cost of clearing its Phil Collins sample, “Starin’ Through My Rearview” was initially left on the cutting room floor before being added to the Death Row-helmed Gang Related soundtrack, post-mortem. But it’s far from a throwaway, capturing Pac at his most paranoid and also his most hopeful, as he pivots from murdered kids to self-actualization in the space of a single verse. It’s also among the very best Outlaw tracks, with E.D.I Mean and Yaki Khadafi tagging in just long enough for Pac to catch his breath and roar back onto the mic with a balance of biographic specificity and universal emotion. This gets at the heart of what makes Pac’s music so powerful and beloved decades later: the personal experience rendered in terms so frank and explicit that young men from the U.S to the Middle East, from Africa to Latin America saw their own lives reflected in this singular American superstar’s challenges. —SON RAW

39. Same Song
prod. Shock G
Digital Underground’s This Is an EP Release [1991]

In January of 1990, 2Pac had his first brushes with the industry as a dancer and roadie for Digital Underground. The Bay Area funk-rap troupe embarked on an arena tour with 3rd Bass and Big Daddy Kane. 3rd Bass had just put out “The Gas Face” featuring a showstopping debut verse by KMD’s Zev Love X. On tour, Zev and Pac hung out a lot behind the scenes, plotting how they could step out of the shadows and, one day, become the main acts.

Exactly a year later, on January 3rd, 1991, Pac had his own “Gas Face” moment, when Digital Underground dropped “Same Song.” Allegedly, Dan Aykroyd had seen Digital Underground perform “The Humpty Dance” and asked them to record basically “the same song” for his—not great—directorial debut, Nothing but Trouble (co-starring Demi Moore, Chevy Chase, and John Candy). The video to the song has arguably aged even worse than the film. Shock G (as Humpty Hump) appears in caricatures of Native Americans, Arabs, and Asians, while Money B cosplayed an Orthodox Jew, all interlaced with random scenes from the movie.

While admittedly derivative of everything that made the band great, the song itself still works as a P-funk-loaded party starter—especially when Shock G subs in Pac with an alley-oop: “2Pac go ‘head and rock this.” With only eight bars, Pac used the mainstream stage to introduce himself with intricate rhymes about his inevitable fame, and how it changed his game with the ladies. “Now I clown around when I hang around with the underground” became a line he revisited frequently. Shortly after, he scored a solo deal with Interscope. Ten months later, 2pacalypse Now was released. —JULIAN BRIMMERS

38. How Do U Want It f/ K-Ci & JoJo
prod. Johnny “J”
All Eyez on Me [1996]

It’s not really a question. Politics and passion trace 2Pac’s entire output, but the choice between the two is as often both-and as it is either-or. Mounted on a mechanical bull, “How Do U Want It” barrels through his psycho-sexual, vaguely Ballardian pursuits before detouring headlong into a gallery of familiar critics. The quick pivot doesn’t work just because it’s what we expect of Pac. His honesty and charisma are often working together, even when they’re in tension. After dispatching C. Delores Tucker with a blunt-force “motherfucker,” he instead pats “Mr. Bob Dole” on the head—reducing another panicked politician to a goofy background character.

As always with Pac, it’s not just what he says, either—it’s how he says it, often gravitating toward language’s stress and cadence as much as its meaning. You don’t, for example, move your hips—you activate them. Clothing isn’t removed, you’re alleviated of it. Every syllable punches the air in hydraulic sequence. Even the song’s “clean” version finds surprising, seemingly unnecessary tweaks: “I’m just a fool in lust/coming to get you on the bus/It’s so ironic, exotic/on the verge of erotic.” The obsession to detail provokes a question you can find in Quincy Jones’ “Body Heat,” as much a precursor to “How Do U Want It” as it is source material: “Why can’t I control my passion?” —GUS TURNER

37. Me & My Homies
prod. Soopafly
Nate Dogg’s G-Funk Classics, Vol. 1 & 2 [1998]

After Pac’s murder in 1996 and Suge Knight’s incarceration the year after, Death Row Records went into free fall. The once-behemoth label was in complete disarray, and no one suffered more than the second wave of artists who had been patiently waiting for their moment to drop: The Lady of Rage, Danny Boy, LBC Crew, OFTB, and MC Hammer found themselves stuck in purgatory, unsure whether they would ever receive an official release date.

But none were more anticipated than the label’s secret weapon and hook god himself, Nate Dogg. Nate’s solo debut, G-Funk Classics, had been advertised for nearly four years before finally receiving a release date in January ’97. After the turmoil at the label, however, the album was shelved indefinitely.

Undeterred, Nate secured his release and signed with the relatively unknown Breakaway Entertainment, where he finally released G-Funk Classics, Vol. 1 & 2 in July the following year. He combined his existing Death Row project with a newly recorded one and packaged them together as a double album.

Despite scoring a Top 40 hit with the Warren G-assisted “Nobody Does It Better,” the double disc largely fell on deaf ears. Without the Interscope machine behind it and with public interest in Death Row fading, many fans had simply moved on. However, interest in 2Pac was still at an all-time high. With the recent leaks of the Makaveli bootlegs—where hundreds of Pac songs suddenly appeared on CD—many rare and previously unheard tracks found new life, including “Me & My Homies.” This feel-good ode to friendship was further proof that Nate and Pac never missed when they collaborated—and what better way to prove that than on a song about never turning your back on your people? —ANDREW BARBER

36. Lost Souls f/ Outlawz
prod. QDIII, co-prod. Sean “Barney” Thomas
Gang Related — The Soundtrack [1997]

The shootouts, the helicopters, the suggestion of liquor as a River Styx pumped straight to one’s stomach is all little more than the setup for one of the slyest and most haunting things 2Pac would ever commit to record: this song’s outro, where he flips the famous lines from “La-Di-Da-Di” (“For all of y’all, keeping y’all in health”) by changing their final word to “hell.” For all the discussion about the supposed shift in Pac’s focus, tenor, or on-record political priorities, the real dialectical tension in his music is between hope and hopelessness. Even here, the warped Slick Rick couplet is delivered so urgently as to suggest there’s something worth seeking on the other side. —PAUL THOMPSON

35. Holler If Ya Hear Me
prod. Stretch
Strictly 4 My N.I.G.G.A.Z… [1993]

“Holler If Ya Hear Me” kicks off 2Pac’s second album like a brick hurled through a squad car window—the kind you throw after watching your stepfather Mutulu dragged through federal court as a “domestic terrorist” and your godfather Geronimo Pratt railroaded by COINTELPRO, after the cops have kicked in enough doors in your neighborhood that every siren feels like a family matter. It’s also the moment where he stops sounding like a promising young rapper and starts sounding like a broadcast from a besieged nation. Over a siren-bright loop, he’s less storyteller than town crier, rattling off police beatings, acute hunger, and surveillance that feel sadly contemporary. The hook isn’t just a chant, it’s a call to arms: if you feel this, you’re drafted. What’s wild is how composed the fury is. Each bar is pitched somewhere between Panther rally and corner argument, the politics braided so tightly into the cadence that the slogans swing a surprising depth. As an album opener, it doesn’t ease you into anything; it sets the terms of engagement, making the rest of the record feel less like a collection of songs than the fallout. —DONALD MORRISON

34. Heartz of Men
prod. DJ Quik
All Eyez on Me [1996]

“Heartz of Men” is a sermon forged in fire. “Hey Suge, what I tell you?” Pac says, addressing his hostile new war-time capo in the song’s intro. It finds the rapper entirely unconcerned with his increasingly dire circumstances: His combat boots are resting on a desk as he smokes a blunt the size of a cigar in a windowless command center, surrounded by piles of banded bills, fondling a grenade, playing with the pin.

It’s one of DJ Quik’s greatest beats, less for its well-worn samples than what he’s able to wring out of them. He finds an odd, droning interlude near the end of “Darling Nicki” and repurposes it as an introductory effect that places the listener in Pac’s churning mind. He takes the same Maceo Parker riff Easy Mo Bee accented “Machine Gun Funk” with and renders it martial, blaring horns as the Carthaginians approach the gates of Rome. He fills the negative space with a Greek choir of Richard Pryor snippets, the skinny dickhead iconoclast trickster freebased and on fire. “I was in every gang” Pryor says, smirking during one of the hookless instrumental breaks. “There was bout five and I was in all of them. Whichever one was winning.”

Pac writing is no less tormented than on Me Against the World, but what has changed is the tenor. What had been an endpoint had become a villain origin story, drained of all fear and depression at the prospect of his demise. He’s too busy to ruminate—he has to lay out tactics for his imagined troops, assess the warring camps on a battlefield, and scan a hellscape full of would-be assassins. It’s hard to resist the urge to dive headfirst into the foxhole with him. —ABE BEAME

33. Life’s So Hard (original version)
prod. Stretch, co-prod. Assassin
unreleased

In Staci Robinson’s authorized 2023 biography of Tupac Shakur, she reveals he used to enjoy smoking weed while zoning out to the Cocteau Twins with school friends. In jail, Pac listened to Eric Clapton to get him through long periods of solitary confinement, while other classic rock acts, including The Cure and Led Zeppelin, taught him about pacing, three-act musical structure, and how songs that deal with pain tend to be the ones that burn eternal. When Pac was on his death bed in 1996, loved ones played Don McClean’s “Vincent” on a loop to try to spark some life.

It’s Zeppelin who producers Stretch and Assassin sample so prominently on the original version of “Life’s So Hard,” the opening guitar licks from “Ten Years Gone” injecting this song with a hypnotic, ghostly riff that’s of a piece with how Pac reduces his ethos: “I’d rather die young than old and broke/That’s why I stay drunk and I constantly smoke!” Released officially in 1997 on the Gang Related soundtrack with fewer verses, a Snoop Dogg cameo, and a bass-driven hyphy beat, the masses may remember a very different “Life’s So Hard.” But among those who can make distinctions between the various Makaveli bootleg tapes, it’s this unreleased version that remains definitive. —THOMAS HOBBS

32. Temptations
prod. Easy Mo Bee
Me Against the World [1995]

There are more overt expressions of emotional distress on 2Pac’s paranoid masterpiece Me Against the World, but I’d argue it’s “Temptations” that delivers the clearest vision of an artist on the verge of a breakdown. The song is a 90s sex jam, which Pac’s peers (and Pac himself) generally in the parlance of flirtatious teasing, horny warmth, and lust framed as romance. From its layered, downbeat opening notes—Easy Mo Bee delivered the instrumental to Pac on the set of Above the Rim in Harlem—it’s clear “Temptations” is operating in a different register entirely.

By the fourth bar, he’s confessed to a would-be paramour that his life is hell, and goes on to paint a picture in which sex is yet another prison, another pressure from within that he must wrestle with on a daily basis. He claims he wants to “be an honest man” and asks himself, “Will I cheat or will I be committed?” The text becomes biblical, the temptation less “sex” than “a hallucination being offered by a dark apparition in the desert in exchange for your immortal soul.” When you consider Pac’s circumstances at the time of the recording—the substance abuse, the legal troubles, the fraying personal reliationships—this framing, these stakes, make tragic sense.

I like to imagine the video was a fun shoot. An all-star cast of friends and collaborators gathered at the Hotel Alexandria in downtown Los Angeles to celebrate Pac’s success and this tremendous album. Coolio plays a bellhop captured on fisheye lens, traveling through the halls of a den of iniquity, full of celebrities and video vixens partying, throwing stacks of fake bills, pouring champagne, enjoying the spoils of Pac’ fame and wealth. But the artist himself was not present. He was serving a year in jail on the other side of the country, in upstate New York, convicted of committing sexual assault, in a hotel. —ABE BEAME

31. Million Dollar Spot
prod. Mike Mosley, co-prod. Femi Ojetunde
E-40’s Tha Hall of Game [1996]

Bay Pac is the best Pac. He’s an American rapper—he ain’t from nowhere, he’s a byproduct of America. He’s from everywhere, and he loved everywhere. But only in the Bay is he hella fun. Being that he’s the son of a Black Panther, and the Panthers are from there, the Bay was able to contain 2Pac’s madness. That place got real, real, real, real revolutionary, real serious. But it also learned to be the funnest place in the fucking world. It did all the woke shit first, and it did all the militant shit first. It’s the only place that can counterbalance the energies. If you listen to “Million Dollar Spot,” it’s a funk bop, they’re talking about getting bread. It starts off with E-40 and he’s telling a story about how he gets down. And the beat is fun! Off top, there’s no way it can get dark. But when Pac comes on, it kind of does. He starts painting this picture: “It was more than just a dream for me.” Then B-Legit anchors it with this braggadocio. Pac ain’t even the star of that shit. Bay Pac is an alive Pac. —ALL CITY JIMMY

30. Made N----z f/ Outlawz
prod. 2Pac, co-prod. Johnny “J”
Gang Related — The Soundtrack [1997]

After Pac’s passing, his unreleased songs were treated like gold dust. If Pac was on it, people were buying—simple as that. The famous Jadakiss line, “You know dead rappers get better promotion,” was likely written about the posthumous run Death Row put together, where nearly every release leaned heavily on unheard material from the label’s departed flagship artist. From the Gridlock’d soundtrack to his own Greatest Hits compilation, the promise of “new” Pac had fans lining up every time.

But the real treasure trove arrived with 1997’s Gang Related soundtrack, which included four previously unheard Pac tracks. And unlike much of Pac’s posthumous catalog, the Gang Related material was top-tier—and “Made N----z” stood out immediately, even among that bumper crop. Pac opens and closes the track with two blistering verses, while the Outlawz hold their own in between. The 360-degree, selfie-style video became hip-hop lore, but the song’s legacy got another boost in 2024 when Kendrick Lamar reworked it into “reincarnated” on gnx. A generational record, twice over. —ANDREW BARBER

29. Krazy f/ Bad Azz
prod. Darryl “Big D” Harper
The Don Killuminati: The 7 Day Theory [1996]

2pac was always acutely aware of how rap was covered, scrutinized, and vilified, and “Krazy” is a metatextual masterpiece. “They say my ghetto instrumental detrimental to kids/As if they can’t see the misery in which they live,” he raps on the opening verse. A highlight of Don Killuminati’s quieter second half, “Krazy” sees Pac at his philosopher-poet peak. In five minutes, he thoughtfully and vulnerably explores his relationship with his mother, the numbing powers of drugs, and the hope and struggle of the underprivileged. Sprinkled with lyrical references that connect to other poignant Pac songs like ”Life Goes On” and “Dear Mama,” “Krazy” exudes this eerie, tragic sense of calm in the face of mortality, like the Seventh Seal chess match.Anchored by a career-making, unflinching verse from Bad Azz, “Krazy” is one of those songs that shows the best of what rap can be. —GRANT RINDNER

28. Bury Me a G f/ Natasha Walker
prod. Thug Music
Thug Life, Volume I [1994]

By the time he started releasing music, 2Pac had already figured out that doubling his vocals could give his already-powerful tenor a unique quality, as if those hyperpersonal verses had become disembodied and simply existed outside of time, place, biography. It could be threatening or invigorating, but it was unshakeably authoritative. “Bury Me a G,” the wistful opener to Thug Life, Volume I found him zagging back for something else. Though dubbed, Pac’s opening verse is unmistakably anchored by a single take—and then buried unusually low in the mix. The effect is to make him sound as if he’s drowning. So when he raps, twice, in the chorus that it’s important he stay focused on money even in the face of death, it sounds for once like he’s trying and failing to convince himself. —PAUL THOMPSON

27. Hellrazor f/ Stretch & Val Young
prod. QDIII
R U Still Down? (Remember Me) [1997]

A blitzkrieg of thunderous, serrated vocals, “Hellrazor” is the sound of a righteous anger that can move mountains. “It’s like a motherfucking trap, and they wonder why it’s hard being Black!” 2Pac rants, more mirror than mortal. His stretched vocals are nearly always on the verge of capitulation and display clear wear and tear from the Newports he’d recently begun chain-smoking. But you’re never quite sure how much Pac believes in what he’s preaching. Although 2Pac pleads with God to “come save the youth” and even references a conventional Christian faith system, a memory of 15-year-old Latasha Harlins being murdered at a Vermont Vista convenience store (“Her little body couldn’t take it/It shook and dropped”) back in 1992 reminds him that this life is all a big nothing, after all.

He ends this song sighing, perhaps in exhaustion or—as it’s tempting to suspect—in relief at the inevitability of being martyred. America might feel like one big trap door, especially if you’re not born into privilege, but 2Pac knows that shouldn’t stop the less fortunate from going down swinging. —THOMAS HOBBS

26. Jealous Got Me Strapped
prod. Blackjack
Spice 1’s AmeriKKKa’s Nightmare [1994]

Nowadays, Jive Records is best remembered as the home of ’90s pop royalty like Britney Spears, NSYNC, and Backstreet Boys. Often overlooked, though, is its role in that decade’s Bay Area rap scene, when its roster included heavyweights such as Too $hort, E-40, Souls of Mischief, and Spice 1.

Another detail that’s largely faded from memory is just how popular Spice 1 was at his peak. His breakthrough came in 1993 with 187 He Wrote, which debuted at No. 1 on Billboard’s Rap/R&B chart. For the follow-up, AmeriKKKa’s Nightmare, he scaled up, enlisting Method Man, E-40, and close friend Tupac Shakur. The Pac-assisted “Jealous Got Me Strapped” quickly became a fan favorite.

Pac also appeared in Spice’s videos for “Strap On the Side” and “Trigga Gots No Heart”—the latter remembered for an on-set altercation between Pac and Hughes Brothers after they fired him from Menace II Society.

Unfortunately, Spice spent much of the recording of All Eyez on Me in county jail, missing out on a potentially career-defining cameo. He and Pac recorded several tracks—many released posthumously—but none matched the chemistry of “Jealous Got Me Strapped,” a song that perfectly reflects the intensity of Pac’s interior life at that moment. —ANDREW BARBER

25. Str8 Ballin
prod. Easy Mo Bee
Thug Life, Volume I [1994]

The origins of Thug Life were confusing at first. We’d heard 2Pac say it, seen the stomach tattoo—but when the Above the Rim soundtrack dropped in March 1994, “Pour Out a Little Liquor” appeared under the Thug Life name… even though it was just a Pac solo track. Without the internet or endless interviews, it felt murky. In reality, it was early promo for a group project Pac planned to release through his Out Da Gutta Records via Interscope and Atlantic Records.

Thug Life, Volume I arrived later that year under a cloud of controversy: censorship battles, corporate pushback, and sample clearance issues. It’s a minor miracle it hit shelves at all. Still, with Pac’s rising notoriety, the album sold despite minimal promotion and bare-bones packaging.

“Str8 Ballin” was not a single, just a closing cut—but it became a cult classic. You heard it everywhere: basketball courts, car stereos, school hallways where kids shouted Pac’s opening bars between classes (“I’m up before the sunrise first to hit the block/Little bad mother fucker with a pocket full of rocks”). Years later, an alternate version (“I’m Getting Money”) surfaced on R U Still Down? (Remember Me), but nothing matched the Easy Mo Bee-produced original. —ANDREW BARBER

24. Brenda’s Got a Baby
prod. Big D the Impossible
2Pacalypse Now [1991]

Bookended by mournful choruses and inspired by a real report out of New York, 2Pac’s story of a 12 year-old girl neglected by her drug-addicted single father and impregnated by an abusive older cousin with whom she thinks she is in love could have very well been a movie he starred in. In fact, Pac wrote the song in the midst of filming a seminal entry in his filmography, Juice. In Sheldon Pearce’s oral history, Changes, Pac’s friend and personal assistant Kendrick Wells remembers the rapper walking into a bathroom (the same place the fictional Brenda delivered her infant unaccompanied) with a cigarette and leaving with most of the song in concept and cadence.

At a time where socioeconomic rap had mostly lost its cache, according to those in Pearce’s book, the sensitivity of “Brenda’s Got a Baby” was disruptive and divisive. In fact, the song “pissed off” Pudgee tha Phat Bastard, a rapper friend of Pac’s. “You do ‘Same Song’ and you’re rhyming with this ill, almost New York flow and then come back with ‘Brenda’s Got a Baby?’ It was a disconnect for me,” he said. Yet for many more, particularly women and our allies, it became an important portrait of Pac’s capacity for conscious storytelling. “Brenda’s Got a Baby” lies at the intersection of two of 2Pac’s core identities: the intuitively gifted theatre kid and the Black Panther progeny. —MANKAPRR CONTEH

23. Can’t C Me f/ George Clinton
prod. Dr. Dre
All Eyez on Me [1996]

The best G-funk beats—Above the Law’s “Black Superman,” Warren G’s “Regulate,” DJ Quik’s “Born and Raised in Compton”—have such a natural groove you almost don’t want them to have vocals. Dr. Dre’s gargantuan instrumental for “Can’t C Me” is one of those tracks, and 99 percent of MCs would be swallowed up by its squealing synths and pounding drums. Pac, in one of his most ferocious vocal performances, tames it like he’s breaking a bronco. He matches the urgency and aggression of the production and the cosmic braggadocio of George Clinton. When he comes in with “Give me my money in stacks,” you feel like you should open your wallet. When he warns “You should’ve never put my rhymes with Dre,” it feels like a genuine threat. It’s the sort of track Pac never could have made before he joined Death Row, and it’s maybe the single strongest argument for what that troubled union added to his artistry. —GRANT RINDNER

22. Trapped
prod. Pee-Wee
2Pacalypse Now [1991]

“Trapped” really does sound like it was recorded inside a prison. The rattle and clank of the drums, the bluesy sorrow of the organ, the sense of claustrophobia that emanates from the slow, probing bassline—it all suggests the concrete and steel depicted in the song’s video, 2Pac’s first as a solo artist. “Even a smooth criminal one day must get caught,” he raps, desperately. “Shot up or shot down with the bullet that he bought.” “Trapped” is full of desperate ruminations that run through the caged mind.

The song began as discarded Ray Luv lyrics that Pac rescued from a trash can and used as a jumping-off point to denounce police harassment and brutality. In one particularly ugly scene, 2Pac describes being hassled by a couple of cops for ID before being thrown against a wall, cuffed, and dropped to the concrete. Like so much of 2Pac’s writing, it would prove prescient. The young artist would later be assaulted by two officers in an eerily similar fashion for the alleged crime of jaywalking. The timing of the attack was particularly tragic: When the premier of the video for “Trapped” was flickering across an MTV screen, its star was nursing his wounds inside a very real cell. —DEAN VAN NGUYEN

21. Smile
prod. Scarface, Mike Dean, and Tone Capone
Scarface’s The Untouchable [1997]

When Pac raps, in the second half of his opening verse—he was always opening songs, even when they weren’t his—of Scarface’s “Smile,” that he has “a message to the newborns waitin’ to breathe: If you believe, then you can achieve,” it has the sting of acidity. He clearly believes, at the very least, in the animating power of hope. But listen to the couplets before it: Pac laments “selling his soul” for material things, but he wishes for a kind of immortalization that seems nearly as stifling as a Faustian Porsche deal. This, of course, is sleight of hand; he’s not trying to dole out advice for others less evolved than himself. He knows he’s the case study. —PAUL THOMPSON

20. Me Against the World
prod. Soulshock & Karlin
Me Against the World [1995]

2Pac moved through 1995 feeling literally hunted, betrayed, and hemmed in by the courts, the streets, and the very industry that sold his pain. “Me Against the World,” built on Isaac Hayes and Minnie Riperton’s lush ‘70s soul and flipped by Soulshock & Karlin, moves with a mournful drift that amplifies the paranoia, isolation, and raw vulnerability in Pac’s opening verse. “Hard-headed bastard,” he raps about himself. “Maybe he’ll listen in his casket—the aftermath.”

What makes “Me Against the World” so quintessential is the it takes in the final verse, when that hopelessness bends toward something like redemption. Pac reminds himself, and us, that the world is less lonely if you participate in it, if you let people in. It’s sobering to hear from a man still nursing five bullet wounds. “They punish the people that ask questions, and those that possess steal from the ones without possessions/The message I stress: to make it stop, study your lessons, don’t settle for less, even the genius asks his questions.” In hindsight, it’s some of the most hopeful writing we got from Pac at this stage of his life, less than two years away finally receiving the serene freedom he could never seem to find during his brief stint on earth. —DONALD MORRISON

19. Ambitionz az a Ridah
prod. Daz Dillinger
All Eyez on Me [1996]

One of the first utterances on All Eyez on Me is awash in paranoia and caked in hellfire, yet delivered with an eerie calmness: “You don’t wanna fuck with me.” It’s indicative of the barely-controlled fury powering “Ambitionz az a Ridah,” an enumeration of 2Pac’s seemingly infinite stressors at the time. “Ambitionz” presages the Makaveli album with its spite-fueled ramblings over the nursery rhyme beat that had been twisted into a deliriously sinister shape. Laughs spill over the ends of lines in which he hints at the possibility of going broke due to legal fees, while in the next breath he almost welcomes the spectre of death as a necessary evil if he wants to move forward in the manner he’s determined to. What makes it a quintessential Pac song is the way in which this fucked up path feels preordained. Even though the raps are tinted a morbid shade, the ease of his recollections belie a sort of joy in the macabre. When Pac spits, “ I’m ready to die right here tonight and motherfuck they life,” you imagine a taut smile plastered on his grill, changing out of his county blues, ready to feel the sun on his face again as he goes after all who have stood against him. —MATTHEW RITCHIE

18. So Many Tears
prod. Shock G, co-prod. Stretch
Me Against the World [1995]

There’s the studio version: somber, contemplative, soulful. Then there’s the way you hear him perform the track live, during the final year of his life, onstage at SNL and the House of Blues: tortured, aggressive, desperate. You hear it in the legendary West Hollywood concert, the emphasis he adds to “Fuck the world ’cause I’m cursed/I’m havin’ visions of leavin’ here in a hearse,” before switching back to the first verse (“I’m not livin’ in the past, you wanna last?”) as his voice gives out. You also see it when Pac cocks his eyebrow and waves his finger near his head at NBC studios in New York, spitting about his time behind bars as his trademark growl crescendoes (“ain’t livin’ well/ I know my destiny is hell, where did I fail?”). The immortal power of “So Many Tears” is that it works in all these forms: as haunting, bracing, and introspective on the album’s iteration as it is during Pac’s last-ever live shows, where he signed off with a roar. Backed on the boards by Shock G—who expertly flipped two of Quincy Jones’ and Stevie Wonder’s most buoyant jams into mournful synth and sax echoes—Pac is the modern American bluesman, a young soldier-poet sending off his dead homies while frankly considering his own demise. It’s not an easy listen in any context. But for anyone wishing to understand who Tupac Shakur really was, it’s an essential one. —NITISH PAHWA

17. Troublesome ‘96
prod. Johnny “J”
Greatest Hits [1998]

By 1996, 2Pac had developed a habit of snatching beats from his rivals and reclaiming them as his own. “Hit ’Em Up” flipped the same sample as Junior M.A.F.I.A.’s “Get Money (Remix)”; “Toss It Up” borrowed from Blackstreet’s “No Diggity.” And with Nas in his crosshairs, Pac reworked the Whodini “Friends” sample that powered “If I Ruled the World.” He debuted the track at his infamous July 4, 1996 show at the House of Blues on the Sunset Strip—two days after It Was Written hit shelves.

“Troublesome ‘96” would later appear on Death Row’s official Greatest Hits release, but not before circulating widely on Makaveli bootlegs that began surfacing in independent record stores in late 1997. As I remember it, this was one of the most popular leaked 2Pac tracks—showing up on nearly every Makaveli CD I picked up. Raw and refined at once, it’s the sound of someone who knew how to pull everyone, and everything, into his orbit. —ANDREW BARBER

16. Pour Out a Little Liquor
prod. Johnny “J”
Thug Life’s Thug Life, Volume I [1994]

Johnny “J” was raised Catholic in Los Angeles. His high-school classmate Candyman, who had a hit with the J-produced “Knockin’ Boots” in 1990, called him “probably the funkiest Mexican you ever met in your life,” and by all accounts Tupac Shakur trusted him.

When he worked with J, Candyman said they could make six songs in a single day, and that pace suited Pac’s breakneck recording style. During their first session, they made the bittersweet “Pour Out a Little Liquor,” which appeared on the Above the Rim soundtrack and the first and only Thug Life album. No other artform celebrates brotherhood like hip-hop, and though the song mourns the dead and incarcerated, the strength of those friendships—and J’s beatmaking—keep the material buoyant. It’s almost like sleight of hand.

Johnny is “the heart” of All Eyez on Me, said Candyman, and during those sessions J learned that he had been adopted. The news shook him. He confided in his friend and Pac responded that he didn’t know his father either. They kept working.

Johnny died in 2008, when he was 39 years old, while serving a sentence at the Los Angeles County Jail for a DWI. Weeks before he began his bid, he called an old collaborator and said he had 80 unreleased songs with Tupac. Other friends of his said his mental health had not been the same since Pac died. He jumped to his death from an upper level at the jail.

A friend of Johnny’s told MTV that “if we could have just 10 minutes to talk, I think the outcome could have been different.” —ROSS SCARANO

15. Me and My Girlfriend
prod. 2Pac, Darryl “Big D” Harper, and Hurt-M-Badd
The Don Killuminati: The 7 Day Theory [1996]

Pac sure made 1996 tough for Nas, who almost certainly had “Street Dreams” in the chamber when he heard the title track from All Eyez on Me vivisect the same Linda Clifford sample. And by Nas’s own admission, after recording “I Gave You Power,” here he personifies a gun, he lost his nerve, explicating the song’s premise in the opening ad-libs as if anyone could possibly miss the point. “Me and My Girlfriend” forgoes the Preemo strings for a little Spanish guitar and scoffs at the notion that this should be a party trick: Pac wants you to know the woman is a gun and the gun is a woman. The lust is palpable, practically dripping off the song, the libinal drive toward death and destruction made eternal: “We’re closer than the hands of time,” weapon and possesser remind one another.

“Me and My Girlfriend” is also the apex of Pac’s virtually unparalleled ability to use his voice as a song’s most interesting percussive element. It’s not even the pocket he finds per se, or the flow—it’s the way he has the hard consonant sounds snap against the drums, the places he decides to slow down or speed up words. It means that, when he notes “We all soldiers in God’s eyes,” it’s delivered with the startling certainty of a cosmic truth. —PAUL THOMPSON

14. Death Around the Corner
prod. Johnny “J”
Me Against the World [1995]

“Death Around The Corner” came to me as a song when I was in my mid-20s. I had just lost a friend to a mass shooting and was distraught with emotions I hadn’t experienced before. Simultaneously with the murder of my friend, several other people I’d known since childhood passed in rapid succession. I got into boxing, punching a bag for hours until I sobbed or lost the ability to breathe, sometimes both. It was around this time that “Death Around the Corner” came up on shuffle. I stopped boxing for a moment and imagined a world where my friend was still alive, and then I imagined what his killer looked like (I purposefully have never seen the face of the killer), then I punched the bag hard as 2Pac rapped about what it’s like to lose so many people that everything feels unsafe; to his credit, they did kill him. He was right to feel unsafe. In the same way, after my friend’s murder, the world only became more dangerous for trans people but especially in this country. 2Pac’s excellence with this song is he brilliantly captures the emotional essence of being aware of the threat of violence while processing insane levels of compound grief and fighting the desire to survive combined with the reality of the violence of surviving in this world. I’ll forever be grateful for this song. —ERIN TAYLOR

13. Never Had a Friend Like Me
prod. Johnny “J”
Gridlock’d — The Soundtrack [1997]

The first verse is tectonically powerful, if uncomplicated: Pac pledges his undying loyalty to a friend who’s just been sentenced to life-plus. (“And you wonder if these white judges like us,” he sneers.) But the chorus is flipped on its head late in the second verse, when he invokes the then-President, who Pac imagines “smoking weed, bumpin’ this beat.” This is an artist who grew up among radicals, saw his mother tossed aside by the liberal intelligentsia when she became passe, and had seen he and his contemporaries held up by government leaders as a corruptive force that needed to be eradicated from society. Pac—who clearly got a kick out of his correctional facility being named Clinton—understood how valuable a foil he was to these people, how their careers, their power was derived in large part from demonizing him. “You ain’t ever had a friend like me.” —PAUL THOMPSON

12. Hit ‘Em Up f/ Outlawz
prod. Johnny “J”
single [1996]

2Pac wasn’t the first artist to bring pure glee and gaiety to a diss track (real nursery rhyme heads will remember “Yankee Doodle”), but 20 years on from his scathing Biggie condemnation, “Hit ‘Em Up” still feels like a culture shift. You know the history: Incensed over “Who Shot Ya?” which Pac reasonably interpreted as an admission of involvement in the Quad Studios, Pac brought his “superhuman” fury into the Can-Am studios with Dramacydal, deploying it like napalm over a Temptations flip and cutesy “Take money” sample swiped from Bad Boy and sunny enough for a school dance. The contrast only makes Pac’s no-shit threats of violence more caustic; in context, “fuck peace” goes far beyond Kendrick’s Superbowl smile. And it can be difficult to hear two men who died too young goad one other to blows. But it’s also an instruction on the border between hip-hop and pop, and the new frontiers of commercialization that created the very concept of a “Taylor Swift diss track.” We savor beef that’s public, cruel, and complete with a piping-hot chorus—Pac codified our taste for it. —HATTIE LINDERT

11. Picture Me Rollin f/ Danny Boy, Skye, and CPO
prod. Johnny “J”
All Eyez on Me [1996]

“Picture Me Rollin” should have been the final song on All Eyez on Me. 2pac’s life was a rolling from one place to the next, from New York to Baltimore to California. Even after death, Tupac kept moving; his ashes found their final resting place in Soweto. The melody samples Kool & the Gang’s “Winter Sadness” and that song’s elegiac tone puts a note of tragedy behind Tupac’s lines: “Any time y’all wanna see me again / Rewind this track right here, close your eyes.” The song is explicitly about Shakur’s 1994 trial that sent him to prison, but Pac’s genius is that the specifics of his life become mirrors for our own. There’s rarely been a better song to play when leaving a complicated hometown, a shit job, or any other chapter of pain that deserves a middle finger and a beatific smile. —EVAN MCGARVEY

10. To Live and Die in L.A.
prod. QDIII
The Don Killuminati: The 7 Day Theory [1996]

On an album that functions, with bone-chilling prescience and scorched-earth fatalism, as perhaps the most unnerving send-off to mortal life ever recorded, nothing sounds as much like the afterlife to me on Makaveli’s Don Killuminati than “To Live and Die in L.A.” It’s the only ostensibly happy-sounding song on the album; the Spanish guitar-laden “Me and My Girlfriend,” famously flipped a few years later into Jay-Z and Beyonce’s first hit single together, is more a death pact than pledge of commitment. But here, over a sped-up sample of Prince’s “Do Me Baby” produced by Quincy Jones’s son QDIII (how’s that for a liner note flex?) Pac is all smiles, jokes, and gratitude. The result is one of the greatest songs ever written about a city, and a eulogy for everything Pac loves—not sent from the fiery pits of whatever hell he delivers “Bomb First” from, but a heavenly place: a convertible doing 90 on the 405, the Santa Anas ripping by, Power 106 or KDAY turned as loud as possible. —JACKSON HOWARD

9. Keep Ya Head Up f/ Dave Hollister
prod. DJ Daryl
Strictly 4 My N.I.G.G.A.Z… [1993]

Consider the gaping hole in Tupac Shakur’s legacy if the righteous spirit had not struck on the day he wrote “Keep Ya Head Up.” The song is one of the pillars of his reputation as a socially conscious prophet; a declaration of solidarity with women, the poor, and the anti-war movement, forever held up as evidence of an innate morality and wisdom. His messages are facilitated by producer DJ Daryl, who identified in the song “Be Alright” by funk-freaksters Zapp the sound of classic civil rights soul. Taking his cues from the original, Pac tunes his voice to a sweeter, more melodic croon; his vocals are appropriately low in the mix, further softening their edges. The final piece of magic is Dave Hollister’s interpretation of “O-o-h Child” by The Five Stairsteps, a song Pac had long loved. This message of hope as a renewable resource surely inspired the rapper to look deep within for something equally sanguine. He voices his support for Black women as they face the everyday problems of a misogynist, patriarchal society, taking the opportunity to declare his pro-choice position (“And since a man can’t make one/He has no right to tell a woman when and where to create one”). It’s a moment that’s rightly celebrated because of how rare such assertions have been in popular music before and since. —DEAN VAN NGUYEN

8. Hail Mary f/ Outlawz
prod. Hurt-M-Badd
The Don Killuminati: The 7 Day Theory [1996]

Hail Mary has a special place for me because when my father was dying, it was on a CD that my aunt Janice gave me. I was into everything, but I was really into rock music before my father got sick. “Hail Mary” had the angst that shit like the Smashing Pumpkins and Alice in Chains had. It had the emotion that I needed to relate to for what was going on in my life as a troubled teen in a school for fucked-up kids next to the fucking prison in Vacaville. This darkness that I needed. It was goth as fuck. The production is slow and bluesy; ain’t no chorus like that ever in hip-hop til this day. I might karaoke that motherfucker one day. —ALL CITY JIMMY

7. I Ain’t Mad at Cha f/ Danny Boy
prod. Daz Dillinger
All Eyez on Me [1996]

2Pac wrote prolifically his entire life and his time in state prison at Clinton Correctional Facility, from February to October of 1995, was no different. Inmate no. 95A1140. No alcohol, no weed, no sex. Instead, reading, exercise, and acts of imagination. Books became a reliable outlet for his roving mind, and letters too. He flirted in correspondence, responding to unsolicited notes from women he didn’t know who mailed him naked photos. Some of those women visited, though sex was impossible. He wrote poems. A treatment for a semiautobiographical movie. Album and song concepts. He turned 24 inside. He thought about Ayanna Jackson and the shooting at Quad Studios. He reevaluated friendships and family ties inside the paranoia-stoking pressure of the H Block cell walls. The place stank. His thinking was sharp, sharper than it had been in years.

There are conflicting accounts of the first recordings for All Eyez on Me. In the authorized biography by Staci Robinson, the title track is finished first. According to Jeff Pearlman’s biography, “Ambitionz Az a Ridah” emerges before the rest. But within the first couple sessions—and this was wind sprints, not a marathon—he cut “I Ain’t Mad At Cha,” a song that sounds like the resigned clarity of incarceration. Produced by Daz Dillinger and built around a piano line from DeBarge, the beat grabbed Pac immediately and he was impatient to record. Kurupt remembers him yelling at the engineer.

Reflecting on friends and family, he composed three verses about three different relationships. The writing is specific, capacious, deadpan (“Oh, you a Muslim now?”). Prison concerns pop up explicitly and subtly—ruminations from a cell; unsated sexual desire—but what stands out is how nonchalant he sounds. All Eyez on Me appears to contain Pac’s entire world and it sounds like everything is on fire. “I Ain’t Mad At Cha” is the cool center, a moment of peace that perhaps prefigures the great reward of death: peace. —ROSS SCARANO

6. California Love/California Love remix f/ Dr. Dre and Roger Troutman
both versions prod. Dr. Dre
single-only/All Eyez on Me [1996]

Be thankful the internet was still young: had “California Love,” the quintessential event single, dropped today, you couldn’t escape the takes. Out on bail, fresh out of jail, and signed to Death Row, 2Pac’s Joe Cocker-sampling, Roger Troutman-featuring, Mad Max Thunderdome-inspired Hype Williams video ode to Cali was originally meant for Dr. Dre’s earliest versions of The Chronic II. Instead it got swept up in Pac’s whirlwind ‘96 recording sessions, morphing from party track to statement of purpose in the process. Featuring enough transplant Californian pride to make the Chili Peppers blush, the single version dominated MTV and BET, fueling ongoing coastal tensions through its existence alone, with Pac’s bravado leaving his perceived rivals with little option but to take this ode to the west as a slight to the East.

Dre’s J Flex-penned opening verse sets the stage, all sunshine, women, good weather and weed, but it serves mostly as a vehicle to get us to talk-box legend Troutman’s all-time chorus, a hook as sticky as the bud circulating in the studio sessions. As soon as Pac gets on the mic, though? All pretenses that this is an equal collaboration go out the window. He lays down the blueprint for every subsequent rapper’s first-day-out track, turns regional footwear preferences into a badge of honor, and cements khakis and locs as the west coast apparel of choice for generations to come (word to GTA San Andreas). Even a lesser album version and Pac disavowing the song (along with “gay ass” Dre) a few months later wasn’t enough to tarnish its spot in the culture, and it remains the definitive ode to the sunshine state, relegating The Beach Boys’ and Eagles’ quaint visions of suburbia and beaches to the dustbins of boomer nostalgia. —SON RAW

5. Pain f/ Stretch
prod. Stretch
Above the Rim — The Soundtrack [1994]

About two minutes into Above the Rim, our main character, Shep, awakens from a recurring nightmare. Whatever passion and potential he once had in his life has been crushed by tragedy, replaced with a weary stare. “Pain,” the song that plays during those opening credits, is about the normalization of sorrow in the hood. In the first verse, Pac seems to rap from the omnipresent perspective of an entity who watches over the community, sensing all the violence that occurs on the streets at once. Or maybe it’s Pac rapping as Shep, the big brother seeing the blocks and faces around him decay, letting those details bleed into the abstract. In the final verse, he drills down deeper: slipping into the first person, a boy in the streets, carrying his gun on the side while he awaits for trouble that is surely coming—always coming. One might take this as Pac embodying Birdie, his character in the film. Even without that context, the portrait is rendered in all its gaudy excess: a lost soul turned cartoon villain, as cold as ice cubes in the summer time. —JAYSON BUFORD

4. 2 of Amerikaz Most Wanted f/ Snoop Doggy Dogg
prod. Daz Dillinger
All Eyez on Me [1996]

Few of 2Pac’s collaborators brought out his joyful side like Snoop Doggy Dogg. Amid the turmoil of the post-prison Death Row era—the warmongering, melancholy, and paranoia that colored Pac’s final months on Earth—it seemed like the very presence of Long Beach’s own could reinvigorate the hardened rapper’s love of life, accentuate his sense of brotherly affection, remind him to reap the spoils of his success. You see it in the video from the Westwood parking ramp, surreptitiously filmed on the day Snoop beat his murder charges. Dancing away their legal blues while blasting Pac’s just-released All Eyez on Me from the Rolls-Royce, the duo’s elation is as infectious as ever. It’s pure freedom, dangerous to express in a world that seems dedicated to bringing you down, yet all the more cathartic for it.

It’s also what animates “2 of Amerikaz Most Wanted.” Here’s Pac partying on top of the world, joined by his slickest comrade in arms, two-stepping over Daz Dillinger’s sparse yet locomotive production (sharpened by a crisp mixing job courtesy of DJ Quik). He and Snoop trade off in seamless, rapid-fire bursts, faithful to their distinct styles while celebrating and uplifting the others. Pac, hungry and rabid as ever (“Now follow as we RIIIIIDE/ motherfuck the rest, two of the best from the Westside!”). Snoop, cool and cunning as you imagined, paying tribute to Melle Mel, M.C. Fosty, and Lovin’ C through his drawl (“It’s like Cuh-Blood gannng-bangin’/ everybody in the party doin’ dooope-slangin’ ”). Ain’t nothin’ but a mothafuckin’ gangsta party.

Of course, the song remains inextricable from the tragedy that followed. The music video, released just months before Pac’s murder, features a lengthy opening scene where he stages some Scarface-style retribution against Puff and Biggie. The darkness was never far behind for Pac. That’s also why his most joyous moments were essential. —NITISH PAHWA

3. I Get Around f/ Shock G & Money-B
prod. The D-Flow Production Squad
Strictly 4 My N.I.G.G.A.Z… [1993]

Conscious thug, sensitive sonneteer, revolutionary outlaw—the mythos of Tupac Shakur was and is malleable to the demands of our often cursed world. But back in the 1990s, it was difficult to build a rap icon solely on the greyscale dispatches of his debut album 2Pacalypse Now. The most basic requirement was hits—hot joints that spill out of car windows and kindle barbecues. And so Pac called upon his former Digital Underground skipper Shock G to bestow on him the kind of beat that would transform a radical scholar into someone people would want to have a beer with. Shock duly obliged, serving up an addictive concoction that makes “I Get Around” such a glorious encapsulation of his humpty-hump creed.

Guest spots from Money-B and Shock himself don’t just bring a sense of D.U. continuity to the young star’s advancing career—they’re necessary party mixers. But Pac is indeed the star here, exuding charisma and locating the right early-‘90s balance of flirtatious playfulness. He boasts about the great burden of promiscuity: “She tell me that she needs me, cries when she leaves me/And every time she sees me, she squeeze me—lady, take it easy!” Considered within historical context, “I Get Around” was a crucial proof of concept: Brenda and Bishop could exist alongside a rapper with A-list pop appeal, and this ball of energy could be harnessed into joyful music. —DEAN VAN NGUYEN

2. Dear Mama
prod. Tony Pizarro
Me Against the World [1995]

Memory is a curatorial practice; “Dear Mama” is a journey through the museum of 2Pac’s tumultuous youth. We see his mother, Afeni Shakur, immortalized as a “crack fiend,” and a “Black queen.” There she is, making Thanksgiving miracles from nothing—and later, when all her “whoopin’” couldn’t set him straight, she’s still there, hugging him through prison bars while he served time for a sexual abuse conviction in 1995.

But selection is also omission: We don’t hear about the Afeni’s 1969 arrest, along with twenty other Black Panthers, on charges of conspiracy to bomb the NYPD. We don’t see her standing trial, representing herself in court, while pregnant with her first and only son; we don’t learn that she was acquitted just a month before 2Pac’s birth. Perhaps “Dear Mama” couldn’t have been 2Pac’s first song to crack Billboard’s Top 10 any other way. Perhaps these details would get in the way of its surprising universality. A disarming and subtly feminist tearjerker on a record otherwise concerned with the daily struggle to stay alive, “Dear Mama” is 2Pac at his humblest, a portrait of a hard-fought family dynamic that’s still soft enough to put on a Mother’s Day mixtape. —ARIELLE GORDON

1. How Long Will They Mourn Me? (f/ Big Syke, The Rated R, Macadoshis, and Nate Dogg)
prod. Warren G
Thug Life, Volume I [1994]

In April of 1993, the members of Thug Life rushed to an Atwater Village studio to tell 2Pac about a murder. It was long past midnight and word had just reached Los Angeles about the death of Big Kato, the best friend and financial backer of Thug Life’s Big Syke. Kato had been carjacked and killed in Detroit for his lowrider and its $2,500 Dayton rims. Gone at 23. According to the streets, the shooter was just 13.

Unable to get immediate revenge, 2Pac and his crew responded with one of the most powerful laments ever written—a mourner’s Kaddish where you can feel the fresh wounds, spiraling rage, and heart-caving agony. “How Long Will You Mourn Me” is not just an elegiac tribute for a loved one who might have otherwise been forgotten to senseless wars, but it also doubles as its own eulogy for 2Pac and the timeless legacy left behind.

No “best” or “greatest” 2Pac song exists. Anything in the Top 20 could be a viable contender for the title. The first pick is a matter of which Pac you value the most. In this case, the final negotiation boiled down to a criteria of what Pac song hits the hardest and most accurately captured the themes omnipresent in his sprawling catalogue.

You can argue that only a 2Pac solo song should top the list. But if you run through his body of work, many of his most indelible anthems feature at least one collaborator. People usually only reference the first 16 bars and outro of “Hit ‘Em Up,” ignoring that the song is mostly the Outlawz. The same with “Hail Mary.” Only about a quarter of the tracks on All Eyez On Me feature Pac solo. This is no accident: one of 2Pac’s central missions was fostering brotherhood.

Raised as Panther royalty, Pac once said that “Black power was like a lullaby when I was a kid.” In his brief adulthood, he aimed to forge the sense of community that had been shattered —whether it was attempting to unite the Bloods and Crips after the ’92 Riots or building his own collectives, Thug Life and the Outlawz. He never had a brother. His biological father was largely absent. His stepfather, Mutulu Shakur was on the FBI’s Most Wanted List and spent decades in prison. So did his godfather, Geronimo Pratt. His allegiance to Death Row was partially rooted in this fraternal desire and intense loyalty. Even the events that led to his death in Las Vegas stemmed from the need to retaliate for a friend who had been robbed months prior.

The prophetic and eerie mortality of “How Long Will They Mourn Me” went far deeper than the circumstances that sparked it. 2Pac spoke to his own lineage and sense of personal loss while simultaneously illustrating the tragically short lifespans of Black men in America. In a deposition given only two years after this song was recorded, Pac told his inquisitors: “In my family, every Black male with the last name of Shakur that ever passed the age of fifteen has either been killed or put in jail. There are no Shakur’s—Black male Shakurs –out right now, free, breathing, without bullet holes in them, or cuffs on his hands. None.”

2Pac was a vessel for pain and struggle—whether it was his ancestors or his kindred spirits on earth. About an hour before “How Long Will You Mourn Me” was recorded, 2Pac and Warren G made “Definition of a Thug N----” The earlier song was conceived after 2Pac first asked Dr. Dre’s younger half-brother about his frustrations, fears, and rage at being left off the Death Row roster. Within the hour, Pac had heat transferred all the fatalism and minor details onto the beat– right down to the .45 on Warren G’s hip.

When the Outlawz broke the news about Kato’s slaying, 2Pac asked for another instrumental. Within minutes, 2Pac painted the picture of their grief: the tears, blunt smoke, and liquor; the fantasy of bringing back the dead by enacting more violence; the need to be strong for those suffering even more. Syke, Macadoshis, and Double R act as aggrieved pallbearers, reminiscing on a friend who never made it back home from an out of state hustling trip. It is a wake recorded live, over an embalming table of sad One Way funk and a teardrop Nate Dogg hook that tunnels so long through hell that it somehow finds its way to heaven.

If you listen closely to Pac’s discography, Kato is everywhere. He’s namechecked on “So Many Tearz,” “Only Fear of Death,” “Where Do We Go From Here,” “Ballad of a Dead Soulja,” “Life Goes On,” and “White Man’s World.” He functions almost as a guardian angel watching from above—similar to Ill Will in Nas’ work or Lil Money in 03 Greedo’s. The one who died before he got a chance to escape, whose memory must be eternally preserved.

From this alchemy of personal sorrow and anguish, 2Pac created a funeral song that offers an ineffable consolation and universal sense of purpose. It speaks to something we all tacitly understand: we never know when God is going to turn the lights out, and all we can do is move with a sense of purpose, love those close to us, and honor the memory of those who preceded us to the crossroads.

Over three decades later, none of the five artists featured on “How Long Will You Mourn Me” would be close to social security age. But only one of them (Macadoshis) is alive and free. Double R is serving a life sentence for murder. The others are now long in the grave. But this song will last forever. It will serve as comfort for the otherwise inconsolable and a reminder to try to cherish our remaining seconds left. 2Pac’s physical form was turned to ashes only halfway through his 24^th year, but three years earlier, he wrote his own requiem. —JEFF WEISS