Tupac Shakur was an extraordinarily prolific artist. The late rapper recorded endlessly in his five year career. So how do you narrow down the 25 best songs ever when a rapper recorded such a massive amount of music? It ain't easy. But nothing about Pac ever was, really.

People love to classify Tupac as "complex" or a "contradiction"—and while it's accurate (after all, what human being is not complex?) the description doesn't fully embody who Pac was, or his work. Mostly, he was a person with passion—for his community, for his friends, for his life, though he talked so often about death.

Maybe therein lies the idea of extreme complexity and contradiction that's become so tied to his legacy. But even all of his talk of death was in line with his overall perspective, those ideas that found their way into the bulk of his work.

Pac was about not only exposing oppressive systems, but examining the way those systems worked in black communities— how the effects of systemic degradation lingered in the homes and minds of black folk like himself. Never did he remove himself from the equation. His musings were not those of an outlier. Instead, he injected himself and his own moral failings into his music— that raw vulnerability is part of what made him so relatable, and his narrative so powerful.

This is a list of 25 of his best songs, not the most important, not even the most impactful, though the songs listed here did play a significant role in defining his legacy. These are his best. Debate away.

  • 25

    "Against All Odds"

    2Pac was never one to hold his tongue and throughout his career found himself at odds with numerous rappers for a variety of reasons. While "Hit Em Up" is obviously one of the most scathing diss tracks of all-time, "Against All Odds," which takes aim at everyone from Nas to De La Soul, was more nuanced. Not quite as emotional as some of his other disses but just as passionate, Pac lays out his beef with Puffy, Nas, Mob Deep, Dr. Dre, and Jimmy Henchman, while claiming it's the "truest s--- I ever wrote." That's debatable but it's one of the standout songs on Don Killuminati: The 7 Day Theory, which is arguably among his best bodies of work.

  • 24

    "Who Do You Believe In?"

    One of the best offerings from Pac's posthumous releases, "Who Do Believe In?" shows up on 2002's Better Dayz. While a lot of the material released after his 1997 death is sketchy to say the least, mostly because it doesn't have his creative input, "Who Do You Believe In?" is a definite standout because of its content and delivery. This song embodies what Pac did best—offer an introspective view on his community and his place in it. On the first verse of the world weary song that finds him questioning and ultimately finding faith in God, he turns his eye outward, tackling the infiltration of CIA crack into the community and the lasting effects of systemic oppression:

    "I see mothers in black, cryin', brothers in packs dyin'/Plus everybody's high, too doped up to ask why... Asked my homie on the block why he strapped, he laughed/Pointed his pistol as the cop car passed, and blast..."

    On the second verse, he turns his conflicted reflection inward.

    "Can't close my eyes, ‘cause all I see is terror/I hate the man in the mirror/‘Cause his reflection makes the pain turn realer..." The song encompasses the best elements of Pac's lyricism, and stands as among the best in a massive catalog of music.

     

     

  • 23

    "Blasphemy"

    Pac's reflections on religion and its impact on black folk—how it swayed our ideas of morality and his own inner-turmoil of coming to terms with his faith despite his often violent reality make for some of his most interesting work, and directly influenced those that would come after him, including Kendrick Lamar, whose musings on faith, spirituality, mortality and morality have placed him in an elite league. Those themes are seen on 1996s "Blasphemy," one of the most haunting tracks from Don Killuminati: The 7 Day Theory.

  • 22

    "Never Had a Friend Like Me"

    Another gem from Pac's soundtrack appearances, "Never Had a Friend Like Me" appeared on the soundtrack for his film, Gridlock'd. Again, here he's paying homage to the homies, pledging to let him get the "last shot of Hennessy" because he's so loyal, and holding his homie down, even after he gets locked up.

  • 21

    "Bring the Pain"

    "Bring the Pain" is probably one of the best-produced tracks Pac appeared on, with Jodeci's DeVante handling the production on the haunting track which appeared on the double-album, All Eyez On Me. It's 2Pac at his most sinister. Pac's boastful lyricism is served well by the creeping, storytelling beat, making it easily one of the most notable songs on the entire project, and one of Pac's more memorable offerings.

  • 20

    "Picture Me Rollin'"

    This song is another standout from All Eyez On Me, an album that was probably Pac's messiest in terms of scope and perspective (though arguably best produced). "Picture Me Rollin" featuring Big Syke and CPO, found Pac in his element, as he celebrated being free, in spite of haters who he thought were trying to hold him down. "They got me under surveillance, that's what somebody be telling/Know there's dope being sold, but I ain't the one selling..." 

  • 19

    "White Man's World"

    There are few that could relay a message like 2Pac and "White Man's World" is one of those passionate tracks that displays the unbridled energy as he talks about what it's like being "born black in this white man's world." Affirming and insightful—"Help me raise my black nation, reparations are due...."—this song illustrates what Pac does best. From lamenting the industrial prison complex to shouting out  political prisoners like Geronimo Pratt and Mumia Abu Jamal (Pratt was released after serving more than 27 years in prison), Pac's freedom message was clear as ever here.

  • 18

    "Cradle to the Grave"

    A favorite from 1994's Thug Life Vol 1., "Cradle to the Grave" was one of the album's defining moments, largely because of a quotable, telling opening verse from Pac: "June 16, 1971, momma gave birth to a hell raisin', heavenly son.The rest of the crew is served well on the track, but it came to be a signature Pac song--and one of the best early examples of the fatalism that would come to define his persona after Me Against the World.

  • 17

    "If I Die 2Nite"

    People like to say that Pac was all passion, but wasn't very lyrical. This is one of the songs that proves he had bars when he opens with, "They say pussy and paper is poetry power and pistols...A memorable moment on his super introspective album, Me Against the World, Pac's lyrics are why he remains one of the hip-hop's greats.

  • 16

    "Holler If Ya Hear Me"

    From 1993's Strictly 4 My N.I.G.G.A.Z., "Holler If You Hear Me" is another song that embodies Pac's philosophy, the same ideology that propelled him to legend status and has an entirely new generation quoting his lyrics, inspired by his passion. Recorded in the aftermath of the 1992 L.A. riots, you can hear the anger in what sounds like a rallying cry:

    "To my brothers on the block better stay strapped, black/And accept no substitutes/I bring truth to the youth tear the roof off the whole school/Oh no, I won't turn the other cheek/In case ya can't see, that's why we burned the other week..."

  • 15

    "Starin' Through My Rearview"

    "Starin' Through My Rearview" is another gem on the Gang Related soundtrack, where he teams with The Outlawz. The soundtrack was released in 1997, after his death, and maybe shows a little bit about the direction Pac was going in. The beat is a little slicker, the delivery a bit cleaner, while 2Pac offers his signature ghetto weary rhymes.

    "Now, I was raised as a young black male

    In order to get paid, forced to make crack sales/

    Caught a nigga so they send me to these overpacked jails/

    In the cell, countin' days in this livin' black hell," he raps in a message that feels as relevant today as it did back then.

  • 14

    "Me Against The World"

    The song from the album of the same name helped set the theme for what's often argued as 2Pac's best work alongside The 7 Day Theory. While the track is upbeat, even though much of the album veers into heavier, melancholy territory, "Me Against the World" is a song about the block. Pac again singles out police terrorism ("Stress in the city, the cops is on top of me") and wonders if black folks will make it out of oppression and the ills it's born before turning it back to himself, and where he stands in the midst of everything that's happening.

    "The question is, will I live? No one in the world loves me... Don't wanna make excuses/'Cause this is how it is; what's the use?/Unless we're shootin', no one notices the youth..."

  • 13

    "Brenda's Got A Baby"

    The standout on 1991's 2Pacalypse Now, "Brenda's..." caught hip-hop fans' attentions because it was still rare to hear the sort of empathy and compassion 2Pac expressed so well as he told the story of a tragic teenaged mother.

    "Now Brenda really never knew her moms and her dad was a junkie--puttin' death to his arms/It's sad 'cause I bet Brenda doesn't even know/Just 'cause your in the ghetto doesn't mean you can't grow..."

  • 12

    "It Ain't Easy"

    Capturing the same vibe as "Me Against the World," the upbeat track and Pac's calm delivery counteracts the layered message he's relaying on "It Ain't Easy." Pac spent a lot of this album talking about prison—evading it, its affects on the community, and why so many black men end up there. On this track, he's telling a day-in-the-life story about how and why his life "ain't easy," and it's among the best on the album.

  • 11

    "Krazy"

    Most Pac fans won't name "Krazy" as their favorite from Pac's haunting Makaveli album, Don Kuliminatti: 7 Day Theory, but in its subtlety it becomes one of the defining tracks on the project. Pac reflects on his life here, while always being aware of how outside realities have both inspired and deterred him from his path. That reflection makes him feel "crazy." Basically, he's as relatable as ever on the song—both assured and vulnerable as he talks about his life and the space he occupies.

    "Last year was a hard one, but life goes on/Bumpin' my head against the wall, learnin' right from wrong//They say my ghetto instrumental detrimental to kids/As if they can't see the misery in which they live," he spits on the opening verse.

    By the end of the first verse, he's crying, moved by a letter from his sister: "Dear Mama, don't worry; I'ma watch for snakes/Tell Setchu that I love her, but it's hard today/I got the letter that she sent me, and I cried for weeks/This what came out when I tried to speak."

  • 10

    "Temptations"

    One of the singles from Me Against the World, the classic, star-studded video for "Temptations" was released while Pac was in jail. The song is simple—as he raps about trying to stay true and not give in to temptation but with memorable production from Easy Mo Bee, this track is easily one of Pac's best releases.

    And the video was proof that--despite the divisive reputation that Pac would earn in the following year, he was a highly respected figure in the game--as evidenced by the numerous cameos from stars Ice-T, Pac's old friend Jada Pinkett, Coolio, Salt-N-Pepa, comedian Bill Bellamy, Isaac Hayes, Treach of Naughty By Nature and others.

  • 9

    "Hell Razor"

    This track showed up on the posthumous album, R U Still Down? and is arguably one of the best songs Pac ever recorded. The production sounds untampered with, as Pac rages against the beat, rapping with exasperation and passion, and with anger that teeters on desperation. He pounds along through the song, rapping about oppressive traps set for young black men, ensnared by a system sworn to protect, and the heartbreak of having a loved one in prison and what's it's like to have to lie to them about what's happening in the outside world so that they're able to maintain their sanity. In one chilling moment, he cries out for Latasha Harlin, the 15 year-old girl who was shot in the head by a Korean shop owner:

    "Dear Lord if ya hear me, tell me why, little girl like LaTasha, had to die?/She never got to see the bullet, just heard the shot/Her little body couldn't take it, it shook and dropped/And when I saw it on the news how she bucked the girl, killed Latasha/Now I'm screamin' f--- the world." 

    Again, he grapples with his own mortality-- his reactions to events that have been set into motion, born out of systemic oppression before finally succumbing to the overarching truth at the end of the song: "Mama raised a hell raiser, why cry?/That's just life in the ghetto, do or die."

  • 8

    "Ambitionz Az A Ridah"

    Stamped by production courtesy of Daz Dillinger, this is another one of Pac's signature tracks that became a standout on All Eyez On Me, laced by its stark pianos, creeping, whispering hook, and braggadocio from Pac, who was freshly signed to Death Row. It's one of the best opening tracks in hip-hop history, with Pac announcing himself as hip-hop's biggest anti-hero:

    "So many battlefield scars while driven in plush cars/This life as a rap star is nothin' without heart/Was born rough and rugged, addressin' the mass public/My attitude was "fuck it," because muthafuckas love it/To be a soldier, must maintain composure at ease/Though life is complicated, only what you make it to be..."

  • 7

    "Pain"

    One of 2Pac's most definitive songs, this Earl Klugh-sampling classic was originally featured as a bonus track on the multiplatinum soundtrack for Above the Rim. Unfortunately, despite it's status as a fan favorite, it hasn't been available on that album for years and isn't streaming anywhere online. But it's one of his most indelible songs:

    "They'll never take me alive, I'm gettin' high with my four-five/Cocked on these suckas, time to die/Even as a youngster causin' ruckus on the back of the bus/I was a fool all through high school, kickin' up dust/But now I'm labeled as a troublemaker; who can you blame?"

  • 6

    "Death Around the Corner"

    "Death Around the Corner" is another immediately memorable track from 2Pac's 1994 album, Me Against the World. Pac talked about death almost obsessively, which has undoubtedly added to his legend. But really, his constant death talk—whether by the hand of another, or his own— was more about drawing a picture of the desperation he often felt and expressed, living as a black man in America. Grasping at materialism and surface satisfaction was an illusion for Pac, and even as he dipped through baser songs, he always returned to this thought and concept. Maybe it's best illustrated on this powerful, haunting track.

  • 5

    "Hail Mary"

    Casual Pac fans might list "Hail Mary" as an absolute favorite. Perhaps more than any other song, it captures the mysticism that has circled his legacy since his untimely death in 1997. The creeping production and Pac's dark delivery as he opens the song with one of the most memorable, evocative lines in hip-hop— "I ain't a killer but don't push me"—mark "Hail Mary" as one his most defining offerings.

  • 4

    "So Many Tears"

    "Back in elementary, I thrived on misery/Left me alone I grew up amongst a dyin' breed/Inside my mind couldn't find a place to rest/Until I got that T.H.U.G. Life tatted on my chest," are probably among the most quotable 2Pac bars in his prolific career. The themes he touches on in this song are regulars for him—spirituality, morality and how that intersects with oppressive systems and life in the streets. If you had to name one song that embodies the kind of rapper Pac was, you could offer "So Many Tears" from his album, Me Against the World, and not be off track.

  • 3

    "I Get Around"

    Alongside "California Love" and "2 of Amerikaz Most Wanted," both from All Eyez On Me, "I Get Around" from 1993's Strictly 4 My N.I.G.G.A.Z. is probably the most played "Party Pac" song. Digital Underground's Shock G and Money-B show up with the assist on the track about getting around because he can't be tied down. Throw this song on, and it's guaranteed to get an immediate reaction, solidifying it as among Pac's best songs.

  • 2

    "Keep Ya Head Up"

    "Keep Ya Head Up" is another signature 2Pac song, one that you could mention as one of his most determinate as an artist. "Some say the blacker the berry, the sweeter the juice/I say the darker the flesh and the deeper the roots/I give a holler to my sisters on welfare/Tupac cares, if don't nobody else care" might be the line that sums up much of his artistic intent, and the hope that he sprinkles throughout the poignant, almost melancholy track. This song speaks to the heart of his messaging as an artist. The video is dedicated to Latasha Harlins, a 15 year-old girl who was shot in the back of the head in 1991 by store owner Soon Ja Du. Du was sentenced to 400 hours of community service and a $500 fine for killing Latasha, and many activists point to her death as one of the catalysts of the 1992 L.A. Riots. Her death obviously affected Pac, as she's mentioned more than once throughout his work. "Tupac care, if don't nobody else care" is an ode to the community, a declaration of solidarity and intent that carries on to this day.

  • 1

    "Str8 Ballin"

    It's pretty cliche to say that Pac was "complicated" or a mass of contradictions. Really, he was a human being who was concerned with the growth and the upliftment of his people and community in often perilous circumstances. He was young, and at times seemed to struggle with the balance of living and embracing a perspective that sometimes seemed at odds with what was happening in real life, in real time. That passion sometimes veered him off course. But Pac undeniably had a heart for the people, and that comes through in his storytelling. It's evident here, in "Str8 Ballin," featured on Thug Life Vol 1., four verses that weave a narrative of desperation and the violence born of subjugation over a steady, head-bobbing beat which samples Bootsy Collins. "What could I do? Pull the trigger or watch my n--- die?" he questions at one point. Earlier in the song he seems to answer his own questions in what might be one of his most memorable lines: "And they say: 'how do you survive weighing 165/In a city where the skinny n----s die?'/Tell Mama 'don't cry'/Cause even when they kill me/They can never take the game from a young G." All in all, "Str8 Ballin" is easily one of the best songs Pac ever recorded.