When Tupac Shakur signed with Death Row Records, he had no other real options. Late in 1995, Shakur was stuck in a prison cell, awaiting appeal after being convicted of sexual assault, with no way to pay his $1.4 million bail. Suge Knight came to him with an offer: He’d pay that bail, but Shakur would have to sign a three-album deal with Death Row. Shakur signed it. It was the best and worst thing that could’ve happened to him. By the mid-’90s, Death Row wasn’t just a label; it was an entire environment, one icily controlled by Knight. Dr. Dre, the mastermind who’d started the label with Knight, was already on his way out the door. So the terrifying Knight surrounded himself with various criminal associates, creating an aura of real and constant danger. Shakur, already a star, threw himself into it, and became a bigger star. Under the Death Row umbrella, Shakur went to work, recording the massive and world-conquering double album All Eyez On Me, his most popular album and arguably his best. Then, seven months after he released it, he was dead, shot five times in a car that Knight had been driving. All Eyez On Me stands as the greatest document of an unstable era, a time when rap’s loudest outlaw joined its most dangerous crew and wreaked as much havoc as he could before dying.

Tupac Shakur contained multitudes. There are so many ways to talk about him now that he’s gone; his complexity was key to his appeal. (He shot cops and got away with it.) On the one hand, he was one of he hardest, most believable street-rappers in the entire history of the genre. But on the other, he was a sensitive soul, a writer capable of great empathy and insight. As a teenager in Baltimore, he’d studied ballet and Shakespeare. As a Digital Underground back-up dancer, he’d happily rocked a granny nightgown onstage. As an actor, he only made a few movies, but he immediately established himself as a volatile and charismatic screen presence; if he’d lived, he could’ve been one of his generation’s great movie stars. And in his early rap career, he famously made room for warm-hearted, emotionally heavy songs like “Brenda’s Got A Baby” and “Dear Mama.”

But that wasn’t the Tupac we heard on All Eyez On Me. Instead, he spent the entire vast album in unreconstructed hooligan form, shooting rage in all directions. He never really gets more sensitive than the moment when he pictures his own funeral, almost sounding like he’s looking forward to it. A few minutes into the 132-minute opus, he offered what amounted to a mission statement: “My attitude is fuck it because motherfuckers live it.” He was right. They did. We did.

All Eyez On Me might just focus one one side of the Pac persona, but it still resonates because Shakur was so good at that one side of it. His delivery — brash, guttural, preacherly, bellowed straight from the chest — is the sort of thing that rappers are still trying and failing to emulate. And on All Eyez, he finds ways to project defiance and confidence even on the most pedestrian songs. People love to debate whether or not Shakur was a great rapper, but even asking that question is beside the point. Shakur said things that stuck with you, and that, more than any breathtaking display of technical acuity, is what proves his greatness. And on All Eyez, he was clearly having the time of his life embracing the hardheaded side of his persona. On a song like “2 Of Amerikaz Most Wanted,” you can hear his smile.

And All Eyez also gave Shakur something he’d never had before: top-shelf production. Dr. Dre barely participated in the album, but he’d established Death Row as a home of widescreen sonic excellence. The producers who did the bulk of the work on All Eyez — Tha Dogg Pound’s Daz, Johnny “J” — were coloring in the lines that Dre had already drawn. The production on All Eyez is smothering, all these keys and guitar-ripples and bass tones filling up every available inch of space. That sort of sound gave Tupac heft; he sounded like he had an army of studio musicians behind him. And unlike so many of the guest-rappers who clogged up the album, he immediately burst out of all that oceanic sound. He couldn’t be contained.

And even though Dre was barely involved, the two tracks he did produce are absolute world-beaters. “Can’t C Me” is a platonic-ideal G-funk ride-out record, with its warbly George Clinton guest vocals and its tense little synth-squeals. Like so many of the best Dre productions, it’s practically overwhelming, all these melodic elements coming together into something grand and cinematic. It gets a particularly vengeful vocal out of Shakur, too. And “California Love” — both the superior single version, with those riotous horns, and the remixed version that appears on the album — is just a straight-up classic, a bulletproof party jam that will always evoke a certain time and place. The Hype Williams-directed Mad Max-remaking video remains one of my favorite videos of all time, and Tupac’s opening bars — “Out on bail, fresh outta jail, California dreamin’/ Soon as I step on the scene, I’m hearing hoochies screaming” — are as immediate and exciting as any I can name.

All Eyez On Me is far from being a perfect album. It’s long, longer than most movies, and it’s piled high with filler. (Nobody ever needs to hear “Thug Passion” a second time.) And while there are great guest turns from a few of Tupac’s contemporaries — Method Man, Snoop Dogg, E-40 — way too much of the album is given over to verses from absolute nonentities like the members of Pac’s Outlawz crew. I can’t really call it an influential album, either, though a whole lot of rap double-albums appeared in the years immediately afterward. Instead, All Eyez deserves a place in history because it’s an uneven but powerful document of one of rap’s greatest, most iconic talents — a man who would’ve done some incredible things if he’d managed to stay alive.