The album to start with

Me Against the World (1995)

Less than four years into his solo career, 2Pac already felt like an icon by the time he dropped Me Against the World. There wasn’t a week that went by without the controversial rapper appearing in court or in the gossip pages with rumours about romances with Madonna and Whitney Houston, but he balanced this notoriety with being a fervent defender of black America’s most poor and vulnerable citizens. He resonated not only with the gangsters, but also the people looking to escape from that lifestyle and find inner peace.

He switches between grappling with suicidal thoughts to leading black America on to a path of enlightenment on his third solo album, but its raw introspection makes the rapper sound less like a thug superhero and more like a fragile 23-year-old, struggling to hold it all together.

On the mournful Lord Knows, he’s on his knees reaching out in pure desperation, powerfully rapping: “I smoke a blunt to take the pain out / And if I wasn’t high, I’d probably try to blow my brains out / I’m hopeless, they should’ve killed me as a baby.” His throaty vocals show the wear and tear of chain-smoking Newports, true, but the delivery of his bars from the very back of his throat sounds gigantic; like a God, clearing both his throat and his conscience. This morbid fatalism reaches a crescendo with the bluesy So Many Tears, a late-night confessional where 2Pac sounds like he’s quite literally being stalked by the spectral figure of death – arguably, these songs were precursors to the emo rap sound of the 2010s, with 2Pac one of the first major rap artists to show his peers that there was no shame in crying or making songs from a position of weakness.

Thankfully, these darker moments are delivered with so much heart that they stretch beyond mere self-pity. It also means that Me Against the World’s brighter, more optimistic shifts in tone feel well earned, as a paranoid 2Pac finally starts to let some light back into his life. The beautifully nostalgic Dear Mama, where he warmly pays tribute to the many hardships experienced by his Black Panther mother, Afeni Shakur (“And even as a crack fiend, mama / You always was a black queen, mama”), and the puppy dog romance of Can U Get Away remind us that gangster rappers can be just as soft as the rest of us.

Me Against the World, which was the first US No 1 album released by someone in prison (the rapper was still serving a sentence for sexual assault), was the most fully formed, relatable iteration of 2Pac. Ideas that might have seemed neurotic 25 years ago, such as 2Pac’s suspicion on Fuck the World that America’s prison industrial complex might be the reason he keeps going to jail, also now sound a lot more indubitable, with the artist creating an enduring collection of cathartic anthems for anyone who has ever felt oppressed. This is rap’s What’s Going On.

The three albums to listen to next

All Eyez on Me (1996)

Bailed out of prison by controversial Death Row Records’ CEO Suge Knight, 2Pac went straight to the studio and recorded this epic double disc in just two weeks. He feels like less of a rough diamond than he did on Me Against the World, with a bigger budget and better producers (such as Dr Dre, Dj Quik and Daz Dillinger) marking his transition from compelling rapper to American icon. The tone is primarily a celebration of Los Angeles’ endless supply of celestial funk (George Clinton, Snoop Dogg and Roger Troutman are among the guest stars), sticky weed, hot weather and eager groupies, but 2Pac proves his his social awareness hasn’t been washed away entirely, either. He uses urgent highlight Only God Can Judge Me to ponder: “And they say it is the white man I should fear / But it is my own kind doing all the killing here.”

2Pacalypse Now (1991)

2Pac’s debut remains underrated, with the artist using it to show outsiders just how dangerous America’s inner cities had become. On the poignant Brenda’s Got a Baby, he empathises with a young black teenage mother whose body has been corrupted by an endless cycle of abusive men, while Words of Wisdom sees him boldly attempt to reclaim the n-word as a source of empowerment (“It means Never Ignorant Getting Goals Accomplished”) as he fawns over the more aggressive political ideals of Malcolm X. The best moment is the urgent, mountain-shaking bass of Violent, where 2Pac channels the sound of Public Enemy with a twisted fable on what it’s like to be harassed by police officers just for existing, ending the song by shooting a “crooked cop” in cold blood. US vice-president Dan Quayle called the record’s release “irresponsible”, but 2Pac was more than prepared to live out his words – in 1993, he was charged with shooting two off-duty police officers in Atlanta, though the charges were later dropped.

The Don Killuminati: The 7 Day Theory (1996)

Having switched his name to Makaveli after reading Machiavelli’s The Prince in prison, this posthumous album, which was finished just before 2Pac’s murder in 1996, has a macabre tone that suggests the rapper was living on borrowed time. 2Pac bluntly embraces his contradictions, persuasively asking for black solidarity (White Man’z World), while also calling out half the rappers in New York, including Nas, Mobb Deepand De La Soul, and threatening bloodshed (Against All Odds). On the dread-inducing Hail Mary, which is built around church bells that ring out like death rattles, 2Pac’s thunderous vocals dissect the pitfalls of masculinity as he wonders if black America is “too hardened” to smile. Just like the rest of the album, the song leaves you with a nagging sense that 2Pac was in way over his head with Suge Knight’s Blood-affiliated label and that, behind the anger and thuggish rage, there was probably just as much fear and paranoia.

One for the heads

2Pac – Life’s So Hard (1997)

The haunting sample of Led Zeppelin’s Ten Years Gone never got cleared, so Life’s So Hard was officially released with a different beat entirely, but 2Pac’s unreleased original remains vital and a real insight into what it’s like to live in fear even when you’re on top of the world. 2Pac sounds like a soldier reporting back from the front line, focused and committed to eradicating a faceless enemy, but also well aware he could just as easily end up as another statistic.

The primer playlist

For Spotify users, listen below or click on the Spotify icon in the top right of the playlist; for Apple Music users, click here.

Further reading

The Takedown of Tupac, by Connie Bruck (1997)

This New Yorker article paints a vivid picture of 2Pac’s death, while the suggestion that he died without much money in his pocket, despite his status as US rap’s most important star, points to ongoing exploitation of black artists.

The Rose That Grew from Concrete, by Tupac Shakur (1999)

A collection of poems that Tupac wrote in his younger years, this book showcases a passionate student of Shakespeare who had a real love for bending words and trying to find the right metaphor to fully contextualise what it felt like to be poor.

Tupac Shakur’s Fashion Legacy, by Janelle Okwodu (2016)

With his distinctive bandanas, velour sweaters, opulent diamond rings and a secret friendship with Gianni Versace, 2Pac’s style aesthetic has been ripped off by a whole generation of rappers. This succinct Vogue article does a great job of expressing how the late rapper inspired the looks of pop stars such as Rihanna and Justin Bieber, too.