He was arrested for possession in his freshman year; he'd always been into music, but after that first bust, it began to seem like a prudent career track to pursue. He wasn't looking to become a rapper himself—he figured his Alabama accent and slight speech impediment would hold him back, and anyway, all the rappers he knew were broke. He looked up to street guys who'd become moguls—Eazy E, Master P, Suave House founder Tony Draper, and Rap-A-Lot Records head J. Prince. He began managing the career of a friend's teenage nephew, who went by Lil Buddy, and began buying beats from a local producer named Xavier Dotson, a teetotaling barber-college graduate who worked under the name Zaytoven. When Lil Buddy apparently lost interest in becoming the Lil Bow Wow to Gucci's Jermaine Dupri, Zaytoven urged Gucci to rap instead.

Soon he was making mixtapes and regional hits (like "So Icy," which also launched the career of a hard-nosed MC named Young Jeezy) while still selling drugs on the side. Income from trapping paved over the rough patches in an early career complicated almost immediately by Gucci's legal entanglements, which, in chicken-or-egg fashion, were mostly due to trapping. In May 2005, he shot his way out of an ambush, killing one of his assailants; he surrendered to police on murder charges days before the release of his debut album, Trap House. The charges were later dropped due to insufficient evidence, but a pattern had been established; throughout The Autobiography, a stint in the clink seems to follow every professional milestone the way Tuesday follows Monday.

"It's very challenging," Gucci says in Miami, "to be an artist, a hip-hop artist, and be on probation, you know what I'm saying? Every time anything happens—you violated probation. It's hard to be on probation and travel. You gotta be so responsible. And at that stage of my life, I wasn't that responsible. It was too much for me."

He began making the most of his time outside the system, learned to freestyle without written lyrics, shuttled from studio to studio. Sometimes he'd rap with nothing in his headphones but a kick-snare drum pattern, letting his producers fly in the rest of the music after the fact. He cranked out dozens of mixtapes every year, occasionally stepping on the potential success of his official major-label releases; in his book, he cheerfully admits that giving away a free mixtape called Buy My Album a week before Warner/Asylum released his seventh album, 2010's The Appeal: Georgia's Most Wanted, was probably not his shrewdest move.

Jacket, $1,650, by Prada. Tank top, stylist’s own. Pants, $2,315, by Philipp Plein. Beanie, $16, by Neff. Jewelry, his own.

He hadn't set out to be a rapper, but now it was as if he couldn't stop; in the months leading up to his incarceration, he became even more prolific, listing his studio as his residence so that he could record while on house arrest and churning out mixtape trilogies that anticipate the 2018 trend toward chart-gaming double- and triple-disc rap epics. Much of that material is rapped in a voice furred by intoxication, and a lot of it is pretty dark. (See: The paranoid title track off his 2013 mixtape Trap House III.)

"It's like, 'Damn, man—that guy was going through some shit,’ ” Gucci says of his immediately pre-jail work. "I was just manic in the studio. I had shit that I wanted to get off my chest. I don't think it was so much that I wanted to give it to the world—I just wanted to get it out my head."

“Barack Obama never put a Gucci Mane song on a summer playlist; when you land at Hartsfield-Jackson airport, Ludacris is there, on a sign, welcoming you to Atlanta.”

The hip-hop news site Pigeons & Planes recently suggested that Gucci has released more than 4,000 songs since the mid-2000s. That might be a slightly fanciful calculation—there's only 120 hours of music on his Spotify page, and many of those tracks are duplicates. But also, to discuss Gucci's catalog in terms of sheer tonnage is to miss the point; what's important about this music is how wildly consistent it all is. With his elementary rhyme patterns and stuffy-nosed vocal register, he was no one's idea of a great rapper in the mid-'00s, but he was always a memorable, irresistible one. Most of the time all he's doing is delivering blunt one-liners about slinging dick and dope better than the next guy—or a whole universe of next guys—but he delivers them with charm and flair, dialing street-life self-seriousness way back in favor of an impish sense of wonder, like he almost can't believe he's getting paid for this.