Lil Wayne says he’s the best rapper alive. Is he?
Well, plenty of rappers have made their own claims to “best rapper alive” or even “greatest of all time,” but Lil Wayne is one of the few with a legitimate claim to the throne over the past few years. For one, no less than Time magazine agreed with him, and critics of all stripes have even agreed to consider the question, which in itself lends credence to the boast. His only competition of any stature these days is Jay-Z, but consider this: Tha Carter III outsold The Blueprint III two-to-one both in first-week and total sales.

But Tha Carter III wasn’t only Lil Wayne’s third album, right?
It was actually his sixth official as a solo artist, which doesn’t count mixtapes, nor the many other Cash Money Records on which he appeared. As “Baby D,” he and Lil Doogie formed the Baby Gangstaz (B.G.) and released True Story in the summer of 1995 before he turned thirteen. (Lil Doogie actually changed his rap name to B.G. because Lil Wayne’s mother didn’t want him recording such profane lyrics at that age.) Lil Wayne and B.G. joined Juvenile and Turk to form the Hot Boys in 1997, just before Cash Money signed a distribution deal with Universal in 1998, which gave them the reach to expose the rest of the world to Mannie Fresh’s take on New Orleans bounce production, not to mention Lil Wayne, Juvenile, Birdman and the rest of Cash Money’s talented MC roster.

Was Lil Wayne involved in Cash Money’s breakthrough?
Of course he was! Fellow Hot Boy Juvenile’s classic 1998 record 400 Degreez spawned three absolutely killer singles. The Hot Boyz appeared in the video of the underrated first single, “Ha,” but more importantly, all of them, including Lil Wayne, rapped on the massively successful second single “Back That Azz Up,” which gave him his first taste of the “featured” spotlight.

So, Lil Wayne is to “featuring” as Lindsay Lohan is to “rehabbing?”
Precisely—even this early in his career! After “Back That Azz Up,” he was featured on now-solo B.G.’s “Bling Bling,” which popularized the now-horribly-dated term, and Big Tymers’ “#1 Stunna,” during the initial Cash Money craze of the late 1990s. (He also appeared at length in Birdman’s The Wire-tribute music video for “What Happened to That Boy” despite not appearing on the track.) Lil Wayne would continue to collaborate with other Cash Money artists while honing his craft and releasing four solo albums, through the release of Tha Carter in 2004.

What happened after Tha Carter came out?
Three important developments: 1) Lil Wayne appeared alongside T.I. on Destiny’s Child’s “Soldier.” His verse was ridiculously good, and definitely put him back on the radar; 2) Mannie Fresh left his position as Cash Money’s house producer (which forced/allowed Weezy to seek out a variety of producers and expand his musical palate for Tha Carter II). For example, Dipset’s Develop, from New Jersey, produced “Fireman,” and Jam and Lewis protégé Robin Thicke produced, and sang the hook for, “Shooter”—both quite popular singles and videos; 3) Lil Wayne was named president of Cash Money records, and founded Young Money, which basically gave him the creative freedom to do whatever he wanted to do.

And what did he want to do?
Aside from Like Father, Like Son, an album-length collaboration with Birdman released in 2006? Mainly, hole up in the studio recording verses, often over popular singles’ beats, but just as often over new ones. Tha Carter may have been his breakthrough, but in this era, Lil Wayne truly stepped his game up. To be fair, the first Dedication mixtape with DJ Drama was recorded and released prior to Tha Carter II (and certainly helped its sales), but Lil Wayne truly stretched himself creatively as an MC in this period, which featured the release of the mixtapes Dedication 2 (also hosted/DJed by DJ Drama, before he was charged in early 2007 with racketeering for his promotional mixes) and Da Drought 3.

What’s so great about Lil Wayne’s mixtapes?
Lacking the restrictions of rap as a business, the mixtapes allowed Lil Wayne to break unwritten rules of rap as it existed at the time. For example, many rap artists avoided lyrics that could be construed as homosexual, or, as popularized by Cam’ron, would comically add a “(no homo)” or “pause” disclaimer after such a potential double entendre (all this despite Snoop’s boasts on Dr. Dre’s The Chronic in 1992 about his dick in the mouth of those who would challenge him). On Dedication 2 and Tha Drought 3, Wayne rarely, and only perfunctorily, felt this compulsion (for example “no homo, let ‘em get their queer on” on the “It’s Me Bitches” remix).

What about the whole “monster” thing?
It’s a theme running through the mixtapes and featured performances. Aided, perhaps, by an alleged abundance of syrup/purple drank (which is to say, codeine), Lil Wayne claimed himself alternately a “goblin,” “monster,” “rapper eater,” “alien” and so on. This gothic-monstrous sensibility has since spread through hip-hop, embraced, for example, by no less than Jay-Z on Kanye West’s My Beautiful Dark Twisted Fantasy.

“Featured performances”? I told you he was on a lot of singles!
Yeah. The best of this period were Fat Joe’s “Make It Rain,” the two DJ Khaled singles (“Holla At Me” and “We Takin’ Over”) and Lloyd’s “You” and especially “Girls Around the World.”

And wait—codeine?
You bet! But Wayne also rapped frankly about the (ab)use of codeine and its effect on his emotions on tracks like “Get High, Rule the World” and “I Feel Like Dying,” an impulse that didn’t particularly translate to mainstream rap in the same way as his gothic themes, but certainly influenced underground rappers like Lil B of The Pack. And for the record, he claimed in his notorious 2009 interview with Katie Couric that he no longer abused cough syrup.

What was he up to then?
Well, throughout his “experimental” period, he was also working on Tha Carter III, and it paid off: “Lollipop” and “A Milli” were huge hits (the latter one of the best songs of 2008), and the album sold better than any rap record since 50 Cent’s The Massacre. He also signed a slew of talented new MCs from all over the country (and Canada—I see you there, Drake) to Young Money, whose collaborative album was released in 2009 following the success of the single “BedRock.” In February, Lil Wayne also released Rebirth as lead guitarist and vocalist, with numerous collaborators. It’s nowhere near as bad as most critics claimed, but it’s still a vanity project, so it’s spotty.

And then didn’t Lil Wayne go to jail for a year?
Almost. From March to November 2010, he served eight months of a year-long sentence at Rikers Island for weapons charges dating back to 2007. But he got immediately back to work, recording “6’7”” with Cory Gunz and performing it on Saturday Night Live in December.