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Lil Wayne’s Long, Strange Trip

Lil Wayne’s Long, Strange Trip: Ron Galella, Ltd. / Getty

Ron Galella, Ltd. / Getty

The eighth song on Lil Wayne’s official debut album, Tha Block Is Hot, is called “Fuck Tha World.” This is the hook:

Look, I don’t curse, but in this verse man fuck the world
I lost my father to a gun and made a little girl
And I’m still thuggin’ wit’ my niggas tryna’ keep it real
And I’m still doin’ for my mother and I’m payin’ bills

Aside from the line about “thuggin,’” everything Wayne says in that hook is true. His stepfather had been gunned down. He’d already had a daughter and he was paying his mother’s bills.

He was 17 years old.

Wayne’s new book, a collection of prison memoirs called Gone ‘Til November: A Journal of Rikers Island, chronicles his eight-month long sting in prison in 2010 that sent his career and life in a tailspin from which he’s still reeling. On September 3, he took to Twitter to announce a retirement that he’s probably not going through with. What’s the clear is that the effects of the time in prison and a host of other factors, self-imposed and otherwise, have led to a volatile time for a rapper we’ve watched grow before our eyes.


It’s easy to forget that Wayne started out as a child star. The New Orleans native recorded his first album when he was 12 years old and by the time he was 14, he’d dropped out of high school to be a full-time rapper. By the time he was 16, he brought the phrase “drop it like it’s hot” to national consciousness on one of rap’s most popular and unaging songs, “Back That Thang Up,” and he had a platinum album at 17 as part of the mega label Cash Money Records. Lil Wayne is as much a child star as Disney breakouts Miley Cyrus and Amanda Bynes. There have been underage rappers before (Bow Wow, Lil’ Romeo) but they never were able to transcend their child-star status and become credible adult artists.

Unlike them, Lil Wayne didn’t peak as a teenager. His star only rose and his music only got better with age. Then something unexpected happened: He became the best rapper in the world.

His first two albums, Tha Block Is Hot and Lights Out were critical successes, but there weren’t high expectations for a squeaky-voiced kid who was seen as Cash Money’s little brother and the kid in their rap group the Hot Boyz. Still, he would famously outshine his group mates on songs like “I Need A Hot Girl” where his verses became the most memorized and repeated at parties. Soon, due to strife between Cash Money CEO Bryan “Birdman” Williams and the rest of the rappers on the label (Juvenile, B.G. and Turk), Cash Money was all but dismantled, leaving Wayne as the only rapper left to wave the flag. So he responded by elevating his game and going on a staggering six-year run. His output from 2002 to 2008 is the same type of sustained dominance that Tiger Woods had in golf during his prime. For years, it felt like Woods would be the best in the world forever. That’s what it felt like watching Lil Wayne at the dawn of the 21st century.

Lil Wayne is as much a child star as Disney breakouts Miley Cyrus and Amanda Bynes.

In 2002, Lil Wayne released a mixtape called Sqad Up featuring few of Cash Money’s younger signees. What was immediately apparent was that Wayne had suddenly become an elite rapper. He traded juvenile barbs and traditional rhyme schemes for off-kilter metaphors and a more abstract flow. He was experimenting with his lyrics in ways we hadn’t seen before, but that was only the beginning. Wayne followed up that mixtape with 2004’s Tha Carter I and 2005’s Tha Carter II, each becoming his best album to date and featured a Wayne that would begin to call himself the best rapper alive, something he’d back up while at the same time revolutionizing an entire music industry.

Wayne followed up his successful albums by doing something most rappers with his level of success just didn’t do in the early 2000s: he gave away his music for free. He started releasing free mixtape after free mixtape while also agreeing to appear on songs with any rapper who had his email address. His work rate became legendary, prompting Vibe magazine to do a list of Lil Wayne’s 77 best songs…of 2007. Wayne would notoriously lock himself in studios for days at a time, even keeping studios on his tour buses to record nonstop for the better part of five years. As a result, he became somewhat of a volume scorer. While not every song was a home run—in fact, Wayne probably has as many sub-par verses as great shots—but he created so many songs that even if 20 percent were great that’s still a massive amount of high-level material. When 20 Wayne fans got in a room it was quite possible that each person would have a different favorite verse or moment at the time. It was hard to keep up with his output but he was able to stretch himself to every corner of the musical landscape by doing songs with everyone from Fall Out Boy and Enrique Iglesias to underground acts like Little Brother and L.E.P. Bogus Boys. There was so much Lil Wayne music floating around that it was impossible not to love at least one or two songs or have a few Wayne-isms memorized at a given moment.

But it was 2006’s Dedication 2 that cemented Lil Wayne’s place at the top of the rap world. If Wayne’s run at the top was like Tiger Woods’ run in golf, then Dedication 2 was his 2000 Masters. Wayne took beats made popular by other rappers and put his own lyrics over them, creating what was essentially an album’s worth of fresh material for free. He was wacky and experimental, racking up stream-of-consciousness lyrics that jumped from drugs to SportsCenter highlights in the same line.


What shouldn’t be forgotten here is that Lil Wayne is a New Orleans native and the peak of his run came right after Katrina hit. For those of us who felt Katrina’s devastation on the Gulf Coast there were two beacons of pride flourishing in pop culture: the revitalized New Orleans Saints and Weezy F. Baby.

Mr. Carter felt like he was at home on all of the borrowed beats he used on Dedication 2, floating from subject to subject and displaying a style that eschewed typical song structure of 16 bars, hook, repeat. Instead he just rapped pretty much nonstop for an hour, moving from full songs about the joys of oral sex to his newfound love of various drugs all wrapped in obscure references like the 90s UCLA basketball star twins the O’Bannons.

Dedication 2 felt like Wayne was spreading New Orleans to every person who had been exiled.

When Dedication 2 came out, I was living in Minneapolis for a summer, about as far away from my birth state of Louisiana as possible while still being in the country. We were less than a year away from Katrina and New Orleans was still nowhere near the place it was before the storm. Local businesses were still shut down and so many people were still spread across the country trying to find their way back home. Dedication 2 felt like Wayne was spreading New Orleans to every person who had been exiled.

Wayne is by no means a political activist, but he did give us “Georgia…Bush,” a scathing indictment of the George W. and his lack of support for black people affected by Katrina:

Man fuck the police and President (Georgia) Bush
So what happened to the levees, why wasn’t they steady?
Why wasn’t they able to control this?

Lil Wayne was a steady reminder of the culture and perseverance of a city that was being counted out by people who said it’d never recover. Like post-Katrina New Orleans, Wayne had also been underestimated. Watching him exceed all expectations while keeping the city on America’s minds made it feel like we could believe New Orleans would be the place it once was. While so many of us were spread across the country, we were able to look at Lil Wayne on TV, representing the city and rising to new heights.


When that 2006 summer was over, I returned to college in North Carolina with my head held high. My peers couldn’t stop talking about any number of classic Weezy verses that had come out since school ended. For people who weren’t from the south, Wayne’s emergence as an elite MC seemed to come out of nowhere. For the rest of us, we’d seen it coming ever since he took the challenge of carrying Cash Money Records on his back four years earlier.

Wayne would spend the next three years experimenting with style even more than ever before. His mixtape Da Drought 3 saw him rap over beats to songs like Beyonce’s “Upgrade You” and turn out the most bizarre and somehow simultaneously most creative lyrical yoga anyone was producing at the time:

Put a motherfucker on ice, like the Maple Leafs
That’s a hockey team, and I ain’t on no hockey team
But I’m a champion, where’s the fuckin Rocky theme
Damn, rest in peace, Apollo Creed
I’m a monster, every day is Halloween

By the time Tha Carter III came out in 2008, Lil Wayne was headlining the Grammys. He used the spotlight to send a dedication to Katrina victims, and even though he didn’t win the Album of the Year, Tha Carter III became one of rap’s more monumental commercial releases—even if it showed cracks in his streak of great music. While some argue the album is a classic, it’s a step down from the previous edition of the series and suffered from aims at radio success over quality. Wayne himself has said that the Cash Money higher ups picked the songs for the album and he didn’t even know what songs made it until it was released. While “A Milli” is a five-minute barrage of Wayne offering Dennis Rodman and STD punchlines that’s as impressive as any song in his catalogue—and as unlikely a radio hit around during the time of autotune and simplified jams—the album overall was bogged down by too much filler. Still, “Lollipop” earned Wayne his first chart-topping single and the album was a billboard monster.

Then, Wayne’s career fell apart seemingly overnight. He had spent the last few years publicly lamenting his love of “lean,” a popular mixture of high-strength cough syrup (for its promethazine and codeine), Sprite and Jolly Rancher candy that has been linked to deaths of rappers in the past, and it was clear that his addiction was dominating his personal life. His managers and friends began making public pleas for Wayne to get help as his creativity and unusual wordplay began giving way to less complex rhyme schemes and cringeworthy lines. Like Woods, who was still a top golfer after his infidelities became public and he stopped winning majors, Wayne was still able to create passable music, but he was no longer on the trajectory of greatness we thought he’d be able to sustain seemingly forever. We kept waiting for him to return and win his “majors” again, thinking it was inevitable. But that moment hasn’t come.

To further derail his career, Lil Wayne served a 10-month prison sentence stemming from a weapons possession charge in New York in 2007, which is the subject of his memoir Gone 'Til November: A Journal of Rikers Island. He returned to rap more sober but less focused. Tha Carter IV was a creative failure, and so were the follow-ups to his Dedication series. His lines that exploded with imagery and left-field references were replaced with clichés and lackluster punchlines. Wayne has spent the last half-decade treading water, incapable of finding a consistent output that’s anywhere near what he was able to accomplish when he was rap’s foremost driving force.


As Woods’ divorce led to the emotional strife that turned his career on its head, Wayne experienced a similar emotional separation. Not from a woman but from his “Daddy.”

As legend has it, on the day when 14-year-old Lil Wayne’s stepfather died, Birdman, who was already helping promote Wayne as a kid rapper, picked him up from his house and told him “Don’t cry, I’m your daddy now.” Since then, Wayne has called Birdman Daddy, and their relationship has been one of the most controversial in rap. Wayne spoke in The Carter documentary film about Birdman forcing him to receive oral sex from women in a room full of people when he was just 11. The duo’s penchant for kissing each other on the lips (“So what, I kiss my daddy,” Wayne raps on his Drought 3 tape) has been a source of side-eyes from the over-masculine and sometimes homophobic rap world. And when Birdman’s business dealings forced the rest of the Hot Boyz away from Cash Money, Lil Wayne was the only one who stayed behind out of loyalty—and some aggressive cease-and-desist orders Birdman and company were quick to send out to potential suitors. One viral video from a few years back had Birdman gifting Wayne with a million dollars in cash for his birthday.

But music relationships rarely last, and this one seems to have soured beyond repair. Wayne has always said that his The Carter V would be his final album; almost five years after it was first announced, the album still has not arrived. When he announced on Twitter that Birdman was responsible for the delay, it set of a chain of events that’s turned their loving relationship into a rap feud that would make Biggie and Tupac blush. Wayne has accused Birdman of withholding upwards of $70 million in contract money due him, and each side is accusing the other of holding up Wayne’s final album. Things came to a head in April of 2015, when Lil Wayne’s tour bus was shot 30 times. The rapper accused Birdman of at least knowing about it beforehand and at most orchestrating it. In fact, immediately after the shooting, Jimmy Winfrey, the shooter, called Birdman from his cell phone.

Maybe it’s the years of drugs. Maybe it’s the emotional turmoil of a feud with his “daddy.” Maybe it’s the wear of being a child star who had to provide for his family at an early age and continue to scale new heights as he got older. Maybe he’s just tired. Whatever the case, the weight of being a 32-year-old entertainer who’s been in the public spotlight for two decades has finally caught up with Lil Wayne. Earlier this month, he sent this tweet out to hint at an impending retirement:

Wayne’s retirement announcement was met with an outpouring of anger and support from rappers who have taken Wayne’s style and run with it. Artists like Chance the Rapper have taken Wayne’s blueprint of releasing free full-length projects to the next level by refusing to ever release retail albums, instead using free music to gain fans and provide material for tours.

Wayne’s frequent passively aggressive nemesis Young Thug (he released a mixtape called Barter 6 last year to poke fun at Wayne’s trouble getting his Carter V album out), who’s a direct descendant of Wayne’s school of mixing autotuned melodies and rapped bars to make the difference between singing and rapping almost indistinguishable, shared his heartbreak over Wayne’s announcement even in the midst of their cold war. If anything, Wayne’s retirement tweet reminded the world just how influential an artist he has been.

Whether Lil Wayne’s career is over or not remains to be seen, but it’s doubtful we’ll get that monumental early ’00s run ever again. From anyone. Since Wayne’s tweets have come out, he’s walked back his retirement talk, but it’s clear that he’s ready to walk away. That leaves us the fans with a choice: Do we celebrate his reign of otherworldly output and genius, or do we mourn the years we lost and the potential that he didn’t reach? Whatever the case, Wayne’s run of excellence changed music forever and represented a city when it needed him the most. For that, his hall of fame status is secured.


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