After serving an apprenticeship with New Orleans' Hot Boys and releasing a handful of so-so solo albums, Lil Wayne dubbed himself the greatest rapper alive on his 2005 album Tha Carter II. He then proceeded to back up that claim with a remarkable creative hot streak, producing a career's worth of great mix tapes and guest spots over the next few years. He capped off the run with 2008's Tha Carter III, which sold more than a million copies in its first week.
His material suggested that Wayne wasn't only the best rapper in the hip-hop, but also the weirdest: The rapper's grizzled rhymes were as all-over-the-place as he was, ranging from quick-tongued braggadocio about girls, cash and guns to gut-wrenching expressions of personal pain to instances of pure id like "I can mingle with the stars and throw a party on Mars / I am a prisoner locked up behind Xanax bars," from the psychedelic mixtape cut "I Feel Like Dying."
Born Dwayne Michael Carter, Jr., on Sept. 27, 1982, in New Orleans, Lil Wayne was raised in the tough Hollygrove neighborhood of the city's 17th Ward. At twelve, he hooked up with New Orleans hip-hop label Cash Money and appeared on rapper B.G.'s 1995 debut True Story. Two years later, Lil Wayne formed the Hot Boys along with B.G. and fellow budding rappers Juvenile and Young Turk. At sixteen he released his solo debut Tha Block Is Hot (Number One R&B/Hip-Hop, Number Three pop, 1999).
Subsequent albums Lights Out (Number Two R&B/Hip-Hop, Number 16 pop, 2001) and 500 Degreez (Number One R&B/Hip-Hop, Number Six pop, 2002) raised his profile considerably. But his biggest success came with Tha Carter (Number Two R&B/Hip-Hop, Number Five pop, 2004), which spawned the single "Go D.J." (Number Four R&B/Hip-Hop, Number 14 pop, 2004). He also received critical attention for Tha Carter II (Number One R&B/Hip-Hop, Number Two pop, 2005), which produced the hit single "Fireman" (Number 15 R&B/Hip-Hop, Number 32 pop, 2005) and went platinum.
Following Tha Carter II, Wayne began to release a steady torrent of high quality mixtapes, including Dedication, Dedication 2, Da Drought 3 (which picked up a series from earlier in his career), Da Drought 4, and We Da Best. The mixtape format allowed the MC to experiment with a less regimented style, drawing mostly from freestyle sessions, that proved popular, not only with harcore hip-hop fans but hipsters: In 2007, GQ magazine named him Man of the Year on the strength of his mixtapes.
In spring 2008 Lil Wayne was arrested, following previous run-ins with the law for felony drug and weapons charges. Soon thereafter, Wayne released "Lollipop," featuring Static Major, which reached Number One on the pop chart In June, prefacing the massive success of Tha Carter III, which debuted at the top spot in June 2008, selling over a million copies in its first week—the first album to do that since 50 Cent's The Massacre in 2005.
Subsequent single from the album, "A Milli" and "Got Money," featuring T-Pain hit the Top-Ten. On album track "Mr. Carter," guest Jay-Z (whose last name is Carter, like Wayne) anoints Lil Wayne as his successor as king of rap: "I share mic time with my heir/Young Carter, go farther, go further, go harder." Lil Wayne won eight 2008 BET Hip-Hop Awards, including MVP, and four Grammy's, including Rap Album of the Year.
Wayne announced that his next album, Rebirth, would be a rock album, and began making appearances with a guitar, notably at the Country Music Awards, where he appeared onstage during Kid Rock's performance, strumming inaudibly on a guitar. Advance singles from the album, "Prom Queen" and "On Fire," peaked at Number 15 and Number 33 respectively — far lower than Wayne's previous singles.
Although originally scheduled to be released in April 2009, Rebirth was continually pushed back. (The No Ceilings mixtape came out in October, lest Wayne go six months without releasing new material.) Rebirth was finally released on February 2, 2010, just before the rapper was scheduled to report to prison to serve a year-long sentence on gun possession charges.
In a February 2010 Rolling Stone cover story, Lil Wayne told the magazine that — though he knows plenty of people from his old neighborhood who have gone to jail — he hasn't asked them for any advice on how to prepare. "This is not something you get no advice on," he said. "This is Lil Wayne going to jail. Nobody I can talk to can tell me what that's like. I just say I'm looking forward to it."
Evan Serpick contributed to this story.