I can’t say I wrote the book on Lil Wayne but I did write a book. This was in late 2010, Dwayne Michael Carter Jr was midway through an eight-month sentence at New York’s Rikers Island for gun possession, and I was cobbling together a sort of biography. This book was a cuts job, which meant I assembled information from what other people had written and fudged things into a cohesive narrative while glossing over his relationship with drugs and guns because of the teenage target readership. In the four or five years since this book was released, however, the decline of Wayne’s career has been unavoidable – lacking in creative output and overwhelmingly centred around his legal dispute with his friend and mentor, Cash Money Records’ founder Birdman.  This rift will no doubt fill the pages of his forthcoming memoir. Entitled Gone ’Til November, it is based on the journals that Wayne wrote in prison, documents I too studied as part of my research process. It is said to feature “his thoughts and feelings about spending time in Rikers Island, the people he met, his whole family, his past, his future, and more”. Drake’s in it too, as is a story about a wedding at which he officiated for two fellow inmates and a reception for which he decorated a room with toilet paper and toasted with Gatorade. Rappers apparently love Gatorade. I tried drinking it during the process, to go method. It’s pretty horrible.  For the uninitiated, Lil Wayne was born in New Orleans and is covered in tattoos. No one really knows how many there are but suffice to say he looks like a map. He has grills and a vacillating relationship with various drugs (most interestingly sizzurp, a codeine-based “drink” which is either the cause or death of his creativity). He is famously a southern rapper, short, difficult (and of a difficult upbringing) and now a father of four. He is not the best rapper by any stretch. His voice is awkward, at times tired, with a grating cadence (Sasha Frere-Jones generously compared his voice to Dylan’s in the New Yorker in 2007). But lyrically, there’s something uncapped in how he views the world, thick with pessimism and humour. Be it astute metaphors (“I put up a wall, and they just wallpaper”), absurd references to beetroot (he’s vegetarian), puns (“When it Wayne’s it pours”) or multiple references to the poet Langston Hughes, he is possessed of a skittish talent that is both unfocused and fascinating especially to someone like me who cannot relate to anything he raps about on any level. Except, perhaps, that we are similar in age and both have plans to retire in two years.  For one of the most unusual and prolific artists of the past 15 years, Lil Wayne has recently been anything but. He remains relevant (collaborating with Yung Lean and guests on Solange’s new album A Seat at the Table), but musically has been camped out in Gethsemane twiddling his thumbs over a stalemate surrounding the release of an album.  He was due to release Tha Carter V in 2014 but decided against it, at least under the umbrella of Cash Money Records, the label founded by Birdman. He then sued Cash Money, demanding $51m and a release from his contract, pointing towards all manner of alleged monetary misdeeds. It also transpired that he wanted ownership of the Cash Money imprint he ran, called Young Money Entertainment, as well as the artists he signed: Drake and Nicki Minaj. The row has been playing out for years, intermittently, veering from the silly (throwing drinks at one another) to the serious (Wayne’s tour buses were shot at by, it’s alleged, a “friend” of Birdman). Their love/hate, father/son relationship has played out, Cronus-like, ever since and raises the question as to whether it’s money, attention or creativity which is fuelling the rift and, moreover, whether anyone cares anymore. Whatever. The fight has become white noise, groaning under the weight of its legal contracts, and feels like fodder for TMZ rather than anything concrete.  Gone ’Til November is therefore likely to level out as some sort of battle cry, a literary scream in lieu of a musical one which is a shame, because once upon a time Lil Wayne’s output was tremendous: 12 albums, and double that in mixtapes (all of which came wrapped in makeshift zine-y covers) on which he used to release his most reactive and non-commercial content.  Following Katrina, New Orleans’s comprehensive battering and George W Bush’s utter mismanagement of the situation, Lil Wayne became his home town’s voice. Songs like Georgia Bush, a brutal impeachment of George Bush’s handling of Katrina, and Tha Carter III’s Tie My Hands, which manages to be both accusatory and commercial – “My whole city under water, some people still floating” – were ballads for the disenfranchised south. He put money into New Orleans to rebuild parks and schools, becoming a philanthropist for the city. To me, he feels forever linked to that tragedy.  When Lil Wayne peaked, arguably around 2008, he was lauded as a hip-hop outsider bolstering a genre that had become stuck on the sort of aspirational sheen which made names of rappers such as P Diddy and Jay Z. He had sold more than 3m copies of Tha Carter III album and won a Grammy . But his experimental work with rock (Rebirth, pretty terrible) and a shift away from music (including a confusing period of serious, serious skateboarding) pushed him off trajectory and lyrically, his relevance began to peter out. He cares about New Orleans, and his roots, representing both beyond physical boundaries, but he also cares about drugs, women and oral sex. Popular rap has morphed into something else, hung with emotion and responsibility, less macho and more in touch with the current mood, a mood which doesn’t quite chime with what Lil Wayne represents.  Drake, who, along with rappers such as Young Thug and Future, arguably wouldn’t exist were it not for Lil Wayne, is a case in point and, says journalist Hattie Collins: “You can possibly trace Wayne’s demise in popularity to Drake’s huge rise – which was the time Wayne was sent to prison. It seemed to kill his spirit, his creativity and certainly his output. Perhaps he felt like he just didn’t have anything to say any more – he said it all over that 2004-06 period.”  His greatest error, to my mind, has been how he has adapted to fame. Barack Obama is a fan and has used Lil Wayne as an example of the dangers of fame and aspiration – “our kids can’t all aspire to be Lil Wayne”. Wayne himself has always been sticky with the idea of role models, distancing himself from the responsibility which comes, proxy-like, with fame. Thomas Chatterton Williams, a US author who writes about race relations, notes: “The best role models tend to be those who assume that responsibility. Forcing someone into that [role] seems less ideal than locating people who are less famous but more worthy of the emulation.” This is especially pertinent when you compare Lil Wayne to someone like Jay Z, his one-time peer, who has “consciously attempted to move into that terrain over the past decade or so,” says Williams, citing a recent op-ed in the New York Times on mass incarceration. Unlike Lil Wayne, “Jay Z is aware of his profile and influence and trying to do something with it”.  His maladaptation to fame was further compounded by a recent interview in which Lil Wayne claimed to have never experienced racism, adding that the Black Lives Matter movement was a “wave [that] just went right by me”. He could be forgiven for panicking, choosing to avoid controversy on national TV, but the takeaway felt that this was a man who, upon witnessing his mostly white audience, wrongly translates that as white America embracing black culture. Collins says: “It’s a shame, because at his best, Wayne was one of the weirdest, most interesting MCs in hip-hop who, I thought, had the potential to delve into subject matter with real political depth.”  The past few years have been a catalogue of errors for Lil Wayne. If he’s done something wrong, you can bet he’s been caught doing it. After all, it’s quite unusual for someone of his stature and wealth – estimated in 2015 to be $150m – to actually serve time unless the justice system is at its wits’ end. A comeback is not impossible – but it feels less and less likely. Which is sad, because regardless of his enumeration of criminal records, squabbles and poor life choices, of diss tracks and Styrofoam cups of sizzurp, he is a talent, off-centre, a democrat, a freak, and unswervingly honest to boot. He is, also, content in this very fallibility, which I find both comforting and triggering. So maybe, on that level, we can relate.
As he prepares to release a memoir, Gone ’Til November, we look back at the New Orleans rapper’s career – from giving Drake his big break to becoming the voice of Katrina and his ongoing Cash Money legal battle