The future seldom arrives on time. Proclamations that a certain technology is about to radically alter our everyday lives are almost always proven wrong: There are no flying cars or robot maids; our life expectancies are holding steady if not declining; the iPod did not, after all, destroy the album as a creative format.
But in the 2000s, as hip-hop was being deconstructed and reformed on and by the internet, Lil Wayne—a one-time child star with a chip on his shoulder about established rappers in his native New Orleans, peers from more critically respected cities like Los Angeles and New York, and the ghosts of the genre’s greats—mutated into something like a seer.
His work in that decade, especially the first three Carter albums and the mixtapes released between 2005’s Tha Carter II and 2008’s Tha Carter III, pulled an entire culture into orbit around his tics, his taste in production and vocal processing, even his most technically and formally daring music.
But his career extends back to Cash Money Records’ vaunted late-1990s period, when he was the youngest member of the Hot Boys and was allowed to develop a voice of his own over producer Mannie Fresh’s reimaginations of New Orleans bounce music. While his output since the eight-month incarceration he served at Rikers Island in 2010 following conviction on a gun charge has been uneven and hampered by red tape and litigation, he continues to be one of the most widely imitated MCs on the planet, despite the near-impossibility of recreating his chameleonic style.
To commemorate the release of Tha Carter VI, we set out to rank the 50 best songs in his catalog, be they from retail albums, online-only mixtapes, or one of his legendary scorched-Earth guest appearances. This was a preposterous undertaking, like trying to rank the various pixels of a magic eye poster. We considered over a thousand songs with only one guiding principle about his slew of freestyles over other rappers’ beats: His version had to be better than the original. Not much was disqualified. –Paul A. Thompson
Lil Wayne: “Thinkin’ About You”
Here are some things the almighty Triggerman beat has soundtracked: a six-minute murder fantasy about Mystikal, a celebration of New Orleans’ Magnolia projects, “The Star-Spangled Banner,” Drake’s catchiest grievance, a bounce song about walking like a guy named Ronald, a bounce song about treating a dick like a monkey, a bounce song about Walmart—dozens, maybe hundreds of bounce songs—and this Dedication 5 track. On a technical, lyrical level, "Thinkin’ About You" is a song about missing a woman half-sung in a Biz Markie register. But partway through, Wayne gets distracted and veers into the Rebirth Brass Band’s "Do Whatcha Wanna,” like he's trying to charge up his depleted swagger. Crying over the world's greatest bounce track, finding strength in a second-line standard—it’s so on the nose for a New Orleanian it's hard to believe Treme didn’t do it first. –Sadie Sartini Garner
Listen: Lil Wayne, “Thinkin’ About You”
Lil Wayne: “A Milli”
“A Milli” is an aura exhibition—the most pointed depiction of unadulterated self-belief we may ever hear in popular rap. I was 7 years old in the back of my dad’s SUV when I first heard Lil Wayne’s career-defining heat-check, unaware that music could even sound like this: The celestial Disney movie sheen at the start, the cyclopean bass, the stammering Caribbean uncle blurting “A Milli” nonstop; thanks to Bangladesh, it felt like the whip had three discs playing at once in the CD player. At the time, it felt like Wayne was this all-knowing giant who just happened to be 5’5”. He lived inside of his tour bus like a monk in a monastery, recording new tracks daily. If “A Milli” sounds like egoistic brain vomit from a dude on cloud nine, it’s probably ’cause it was. It’s all so raw that Wayne gets away with so much that would’ve sounded corny coming from anyone that wasn’t him. –Olivier Lafontant
Listen: Lil Wayne, “A Milli”
Sqad Up: “Best of Me”
Let’s not overlook Sqad Up, the New Orleans collective in which Lil Wayne shined in his pre-Carter days. Working with other young rappers—peers, not big brothers—yielded a looser, more playful Wayne who got to test his dexterity over popular instrumentals of the early aughts. Some of his best material from that period shows up on the group’s 2002 SQ4 mixtape, and a prime example is “Best of Me,” which tries out the beat for R&B singer Mýa’s Jay-Z-featuring single of the same name. On the track, Wayne takes cues from Jay-Z putting on an elite display of repetition of wordplay. He was still a teenager, but the flashes of his mixtape-era greatness were clear to see. –Lawrence Burney
Listen: Sqad Up, “Best of Me”
Rick Ross: “Luxury Tax” [ft. Lil Wayne, Trick Daddy and Jeezy]
As Rick Ross tells it, his quietly excellent collaborative streak with Lil Wayne came about through one DJ Khaled. In the late 2000s, both Ross’ crew and Cash Money were in Miami recording at Hit Factory, with Khaled serving as the conduit between them, passing tracks back and forth. It makes sense that a guy who now lives life as a cartoon character linked them up. There’s a kind of bro-ey buddy-comedy energy to all of the Ross and Wayne music, whether they’re pretending to be supervillains on “John” or drifting around the club on “I’m on One.” The best Wayne-Ross song, however, is “Luxury Tax.” This was off the second Ross album, when his bread and butter was J.U.S.T.I.C.E. League production so luxurious it left you in disbelief. What’s even harder to believe is the ridiculous verse Wayne tees it off with. He pulls off a hilarious MLK comparison here, rivaled closely by the one on “Playing With Fire.” –Mano Sundaresan
Listen: Rick Ross, “Luxury Tax” [ft. Lil Wayne, Trick Daddy and Jeezy]
Lil Wayne: “Knockout” [ft. Nicki Minaj]
Let’s get this out of the way: Yes, Rebirth is a disaster full of pop-rock experiments that are too slow, too serious, and too corny. Yes, whoever introduced Lil Wayne to Warped Tour, Guitar Hero 3, and Patrick Stump’s fedora stash deserves a hell of their own making. Nevertheless, “Knockout” goes crazy. The slurred Auto-Tune rhymes and general nonsense are just right for J.U.S.T.I.C.E. League’s production, which aims for Blink-182 but lands at Camp Rock. And Wayne and Nicki, doing some sort of sing-rap-scream, buy into the bit so hard that I’m willing to overlook all the weird Barbie and Ken race play they’re doing. “Knockout” was a rare moment that made the now-tired “rapper turned rock star” shtick actually kinda cool. –Alphonse Pierre
Listen: Lil Wayne, “Knockout” [ft. Nicki Minaj]
Lil Wayne: “I Know the Future” [ft. Mack Maine]
Another casualty of the rampant bootlegging that preceded Tha Carter III’s release, “I Know the Future” is among the most virtuosic in a series of showcases for Wayne’s abilities as a vocalist. While the parallels drawn (sometimes by the artist himself) between him and 2Pac are usually semiotic, here Wayne channels what is perhaps Pac’s signature skill: his capacity to bludgeon his way through a heavy beat while retaining the dynamism and bend in his voice. –Paul A. Thompson
Listen: Lil Wayne, “I Know the Future” [ft. Mack Maine]
Lil Wayne: “Watch My Shoes”
I’m sure that there was a specific fear that came with being a rapper from Louisiana during Lil Wayne’s Dedication 2/Da Drought 3/No Ceilings mixtape stretch in the late 2000s, a sensation not unlike when the South Central Los Angeles neighborhood in Friday heard Deebo riding around on his stolen bike, tucking chains and hiding all valuables from sight. This type of local friendly fire on “Watch My Shoes”—Wayne opens it by asking fellow New Orleans natives Gudda Gudda and close friend Marley G why anyone would start with him—makes the original performances from Lil Phat, Shell, and Mouse On Tha Track almost feel passé. Wayne’s signature rasp bounds with joy as he compares himself to Papa Bear from Goldilocks, likens his enemies to hors d’œuvres, and name checks Betty Boop over the hypnotic, ripe-for-radio beat. –Matthew Ritchie
Listen: Lil Wayne, “Watch My Shoes”
Lil Wayne: “I’m a Beast”
It’s hard not to laugh when Lil Wayne opens this by saying rapping is his hobby. That’s a lie. It’s not even his occupation. It’s closer to a physical condition, his every molecule primed to convert thoughts idle and profound into rhymes. “I’m a Beast” finds him in a druggy flow state, his cadences stretching and compressing as he trundles through a chintzy Sarom beat. He calls himself a beast, a dog, an arsonist, and asks for a drink with no ice because he’s wearing enough. The song is quintessential Mixtape Weezy: off-keel, loose, relentless. Even when the song stops, you’re certain he could keep going forever. –Stephen Kearse
Listen: Lil Wayne, “I’m a Beast”
Lil Wayne: “Bring It Back”
By 2004, the once-formidable Cash Money army was mostly fallen soldiers: Juvenile, B.G., and Turk had split from Birdman and gone their separate ways, and Mannie Fresh would be next. Tha Carter, the first truly great album from Wayne—who’d been rapping professionally for a decade at 21—would be Fresh’s last one as Cash Money’s long-suffering in-house producer. He dials back the belligerence on beats like “Bring It Back,” Tha Carter’s lead single, which fashions Wayne’s stream-of-conscious mindspray into something basically commercial, suitable for elderly people, twerkers, chickens, ducks, whoadies and whoadettes. “Best rapper alive since the best rapper retired!” the intrepid former child star announces toward the end. A couple years later, he’d be right. –Meaghan Garvey
Listen: Lil Wayne, “Bring It Back”
Lil Wayne: “Swag Surf”
Did Taylor Swift and them gentrify the swag surf? You could say that. At least Lil Wayne embraced F.L.Y.’s divine brass flurry first. No Ceilings, his ’09 Grammys victory lap, opens with an unrelenting 4-minute remix of the HBCU classic. Mixtape Wayne does this thing where he adopts the cadence of whatever track he’s stealing from just to prove he could do it better. You see the chrome on this Bugatti, right? It costs way more than that Hypnotik y’all are sipping. With each passing flex and shapeshifting flow he strikes a balance between the punchline magician and the human we maybe don’t give enough credit to: “Lost some real niggas I knew from a long time ago,” laments Wayne. “But heaven or hell, I’m hoping that they be where I’mma go.” –Olivier Lafontant
Listen: Lil Wayne, “Swag Surf”
Lil Wayne: “Weezy F. Baby”
Hip-hop’s mixtape boom in the 2000s is usually written about in industrial terms: rappers working outside their contracts with labels or around copyright law. But at its best, the format also allowed for MCs to creep toward the edges of their own styles or attempt ones they admire; to rethink form or abandon it entirely; to truly freestyle. On the first Dedication tape, Wayne took the instrumental from 8Ball & MJG’s languid “Mr. Big” and snaked through the folds of his brain: he twists the word “professional” into a Gordian knot to fit a rhyme scheme, he pulls up to the valet “in something Americans can’t invent,” and he worries a judge’s sentence will be “an algebraic expression.” It would be tempting to say you can hear each line take shape in real time, but there’s nothing about it that would be legible to us mortals. –Paul A. Thompson
Listen: Lil Wayne, “Weezy F. Baby”
Playaz Circle: “Duffle Bag Boy” [ft. Lil Wayne]
Lil Wayne becomes the spirit of the trap on “Duffle Bag Boy.” His belted hook addresses hustlers, himself, a lady, and challengers expecting him to back down, his delivery dripping with bravado despite the desperation in his words. Whether there’s money owed to him or money to be made, he’s going to get it, he swears over a church band’s worth of instruments. It feels like he’s declaring war against being broke. Tity Boi (still a few years away from his 2 Chainz transformation) and Dolla Boy become bit players on their own song, but that’s OK. When Wayne is in his bag, all you can do is watch him work. –Stephen Kearse
Listen: Playaz Circle, “Duffle Bag Boy” [ft. Lil Wayne]
B.G.: “Bling Bling (Radio Version)” [ft. Big Tymers and Hot Boys]
When the bling era was spoken into being, it was via the voice of an honor student who thought pulling your shirt up behind your head looked cool. Wayne was 16 years old when he did the hook (and, in the video version, a choppy, stutter-stepping verse) in B.G.’s “Bling Bling,” giving the world a word and a lifestyle that, to a certain type of person, would come to signify everything that was wrong with: rap music, Black folks, uncomplicated pleasure and abundance, and probably helicopters, too. Like “woke,” it’s a word that was minted as a token of Black pride that circulated widely, turning into a near-slur now used only by people who buy $550 rhinestone clutches from a sitting president. Pretend for a second you don’t know any of that, though. Pretend you’ve never heard the word at all, and you can see it as Wayne’s first miracle, turning a bit of absurd nonsense language into platinum and making himself into a star. –Sadie Sartini Garner
Listen: B.G., “Bling Bling (Radio Version)” [ft. Big Tymers and Hot Boys]
B.G.: “Niggaz in Trouble” [ft. Lil Wayne and Juvenile]
Washing ’99 Juvenile and B.G. on a track is like winning a home run derby up against prime Barry Bonds and Mark McGwire. Give that honor to a 16-year-old Lil Wayne on “Niggaz in Trouble,” where, over a galactic Mannie Fresh beat with a bassline fatter than a cut of brisket, he’s shot out of a cannon with the intensity that would come to define his mixtape era. “You done pissed off my crew/What y’all gonna’ do,” he raps, blacked out. “Look, nigga, you better put a zip on yo’ trap/Or you will get trapped.” It’s the kind of dick-hanging, foot-on-the-gas shit talk you expect from the fearless young bull of the crew. When that fervor was unleashed, even two of the best rappers in the world had to step aside and let him do his thing. –Alphonse Pierre
Listen: B.G., “Niggaz in Trouble” [ft. Lil Wayne and Juvenile]
Big Tymers: “How U Luv That” [ft. Lil Wayne]
Maybe because he was still in high school at the time, Wayne tended to be given bit parts in Cash Money’s early hits. A theater kid to his core, he took advantage of that limited time in the spotlight to do things nobody else would or could. He’s barely on the title track from the second Big Tymers album, a smooth dollar-tossing cut that feels like a Southern counterweight to “Money Ain’t a Thang.” Sounding much more comfortable rolling around the song’s lush upholstery than Mannie Fresh or Baby, he lets out a little prrrt—a ridiculous and accurate imitation of a chirping late-’90s cell phone. Baby was paying attention. –Sadie Sartini Garner
Listen: Big Tymers, “How U Luv That” [ft. Lil Wayne]
Lil Wayne: “Up to Me”
The first decade of Lil Wayne’s career was largely defined by his ability to embrace the insurmountable sums of responsibility that were prematurely placed upon him. His superstardom came as a result of having to carry Cash Money after the rest of the Hot Boys bounced. He welcomed his first child into the world at 16. But, before all of that, as chronicled in Tha Block Is Hot’s “Up to Me,” an adolescent Dwayne Carter Jr.’s first grown-up test was to reckon with the murder of his stepfather, Reginald “Rabbit” McDonald. With a hardly-deep voice, Wayne addresses Rabbit with a series of life updates: his new status as a father, him earning a hefty amount of his own money as a rapper, and how he’s able to take those funds to take care of his grieving mother. On the hook, Turk lends his close buddy some encouragement, suggesting that, even though he’s at the driver’s seat of his family’s destiny, it’ll all turn out fine. –Lawrence Burney
Listen: Lil Wayne, “Up to Me”
Lil Wayne: “I’m a Ridah”
As the 2000s gave way to the 2010s, Wayne started to become a shell of the consistent rhymer he had been in the Bush era, his flows slackening from verbose bursts to digestible mid-tempos, his taste in beats to remix less audacious and more predictable. So, when I listen to the first Dedication tape, I savor it, knowing I’m hearing a rap legend will himself into being that. Dedication includes the most underrated Wayne remix, “I’m a Ridah,” a 21st century update of 2Pac’s “Made Niggaz.” In a hoarse voice, Wayne almost steals Tupac’s classic out from under him. Pac was a great rapper; here, Wayne’s better. –Jayson Buford
Listen: Lil Wayne, “I’m a Ridah”
Lil Wayne: “I’m Single”
If there is an unofficial breakup anthem for those raised on LimeWire and DatPiff, it’s Wayne’s “I’m Single.” It’s one of the standout melodic songs of his Best Rapper Alive era. Hearing him go through the trials and tribulations of a toxic relationship and how to move on from the dealings of an unhappy relationship with his sing-songy Auto-Tune voice, was a twist for the rapper known for the filthiest sex punchlines. Credit to the touch of vulnerability goes to Drake’s mushy writing and 40’s groggy production that Wayne makes sexier and more emotional. –Nia Coats
Listen: Lil Wayne, “I’m Single”
Lil Wayne: “Sky Is the Limit”
A few times a year, a screen grab of an ancient article from Vibe Magazine titled “The 77 Best Lil Wayne Songs of 2007” (written by one-time Pitchfork contributor Sean Fennessey) goes viral. People who weren’t there find it hard to believe there were 77 Weezy songs in a year worth writing about, while people who lived through it admire the fact it was cut down so precisely. That was arguably Wayne’s most prolific, and most impressive year, despite the fact that his only official release was The Leak, an EP of already-available songs that was basically a money grab dropped on Christmas.
In 2007, if Wayne decided to rap on your beat, it was an honor. The only caveat was that it was no longer your song, it was now his. And no song is a better example than “Sky Is the Limit,” an undeniable mixtape anthem which lifted the instrumental from Mike Jones’ “Mr. Jones.” Wayne performs this track at most of his concerts—where fans sing along word for word—most forgetting it originally belonged to Mike Jones (WHO?!) They’d have a better chance of remembering Jones’ phone number. –Andrew Barber
Listen: Lil Wayne, “Sky Is the Limit”
Lil Wayne: “Momma Taught Me”
Jacking the Roots’ “Star,” Lil Wayne honors his mother by talking exquisite shit. Where the original is melancholic and smooth, Wayne’s spin is mischievous. He condemns pimping and flippantly endorses slavery. He keeps pulling a trigger even after the clip is empty and declares himself Mister Daisy from the backseat of his whip. And he doesn’t simply stay strapped: He eats, sleeps, shits, and bathes with his gat. But he doesn’t draw attention to this ambient absurdity, locking into a groove with the drums and leisurely unspooling his thoughts. In Wayne’s loopy world, the surreal is mundane. Happy Mother’s Day. –Stephen Kearse
Listen: Lil Wayne, “Momma Taught Me”
Lil Wayne: “Get Off the Corner”
It’s entirely possible that 18-year-old Lil Wayne’s response to the idea of imposter syndrome setting in following his stunning debut 1999 Tha Block Is Hot would be “What the hell is that?” The greatest evidence of the teenage prodigy’s self-efficacy is “Get Off the Corner,” the lead single off his second album, Lights Out. Surrounded by sparse drum patterns, blaring horns, and intermittent police sirens, all woven together by Mannie Fresh, Wayne’s nearly five-minute, anxiety-tinged tirade reveals an intense hunger from the Hot Boys’ youngest member. He makes each nook and cranny of the block his home, tweaking his voice to creak and croak with almost every punchline about drug dealing and finishing beefs. By the time the gruff repetitions of “you better get off the corner” trail off in the outro, it’s clear that “Get Off the Corner” was the final warning shot that Wayne was out to dominate rap’s Monopoly board. –Matthew Ritchie
Listen: Lil Wayne, “Get Off the Corner”
Lil Wayne: “Diamonds and Girls” [ft. Curren$y]
Despite being overshadowed by popular tracks like “Prostitute” and “I Feel Like Dying” from the unofficial and often overlooked Da Drought Is Over 2, “Diamonds and Girls” was the song I spent the summer reciting to memory on the streetcar from Uptown to the Riverwalk in New Orleans. Wayne approaches the bouncy Prince sample like a world-famous stand-up comedian testing out new ideas at a low-capacity comedy club, cracking hilarious one-liners (“And here’s my most funniest joke–I’m broke”) and dishing out sharp, economical similes like an exercise in creative decluttering. In the second verse, one of the best of the mixtape era, he accelerates his cadence and effortlessly rhymes everything you can imagine with “diarrhea.” It’s a quintessential Wayne closer that sticks with you decades after the first listen. –Nigel Washington
Listen: Lil Wayne, “Diamonds and Girls” [ft. Curren$y]
Lil Wayne: “When You See Me”
Also known as “B.M. JR II,” this leak, usually dated to the period between Carter II and III, showcases some of Wayne’s clearest writing and most advanced technique. He scurries from pocket to pocket in the cascading beat, his always-elastic voice feigning strain to call attention to rhyme schemes as he stretches them to cartoon proportions. The second verse is one of the most breathless and breathtaking runs in his whole catalog. By the time he promises to “appeal when they extradite us,” you can’t imagine a court disagreeing. –Paul A. Thompson
Listen: Lil Wayne, “When You See Me”
Bobby Valentino: “Tell Me (Remix)” [ft. Lil Wayne]
At the pre-show of the 2007 MTV Video Music Awards, Lil Wayne, filling in for T.I., had to come up with an impromptu guest verse to tack onto Nicole Scherzinger’s by-the-books single “Whatever U Like.” With a casual flow that made it unclear whether his verse was already written or freestyled on the spot, he killed it by hitting Nicole with his flirty swag: “Can’t pronounce her last name, so it should be mine.” That’s Wayne, a natural smooth-talker who knows how to give an edge to R&B tracks. One of his best moments in the genre was on the remix to Bobby Valentino’s “Tell Me.” The need to keep things radio friendly is what really expands his imagination, and, over a mad violin beat by “Thong Song” creators Tim & Bob, he goes in for two intimate yet restrained verses where he’s eyeing a baddie from across the bar. It’s like one of those old Hays Code rom-coms that tiptoed around sex, all innuendo and all the better for it. –Alphonse Pierre
Listen: Bobby Valentino, “Tell Me (Remix)” [ft. Lil Wayne]
Lil Wayne: “Hustler Musik”
Wayne already wrote the “Hustler Musik” blurb when he compared himself to Scarface with a cigar dangling off his lip. The song sounds exactly like that, pure motivation and calm ruthlessness in three verses. Super-charged with T-Mix and Batman the Producer’s live organ, brass, bass and drums, “Hustler Musik” is like if the top floor of a hotel were a rap song, Wayne channeling shiny suit-era Biggie and Jay as bars tumble out in a relaxed, methodical flow. There’s no hook in his catalog as effortlessly cool as the head-to-the-sky mantra here. And Wayne has this way of transforming the typical rapper documentation of the ‘fit into a scientifically precise poetry: see how he flits from describing the Nina in his palm (“now I’m masturbating”) to drawing out the assonance of “Bathing Ape, Yves St. Evisu what I stay in.” –Mano Sundaresan
Listen: Lil Wayne, “Hustler Musik”
Lil Wayne: “Hoes” [ft. Mannie Fresh]
When they got together, Lil Wayne and Mannie Fresh were like teenagers in a 1980s sex comedy. Nothing else was on their minds but getting ass. But compared to earlier joints from the pair, like “Break Me Off” and “Drop It Like It’s Hot,” Tha Carter’s “Hoes” is less concerned with handjobs or whatever but the characteristics of the girls they’re bringing back to the bachelor pad. Wayne’s list includes: WNBA players with straight backs, short-haired girls who look like “The old Halle Berry/Or the broke Toni Braxton,” and the freaks around the way. Mannie, a true vet of the player game, gets more specific: Shelly who liked to bump Pac and eat fast food, Shawna the pothead, and Patrice who went to jail for trying to stab her niece for also fuckin’ with Mannie. It’s about as mature as their horndogging gets. –Alphonse Pierre
Listen: Lil Wayne, “Hoes” [ft. Mannie Fresh]
Lil Wayne: “Shine” [ft. Hot Boys and Mannie Fresh]
At first, “Shine” was just an album cut tacked on Lil Wayne’s sophomore LP, Lights Out. But as 2025 streaming numbers reflect, it almost instantly became that record’s most popular track. “Get Off the Corner” was a great choice for the first single, but “Shine” was what the people really wanted. You heard it at parties and DJs played it in the clubs; by the summer of 2001, Cash Money was all but forced to release it as a single. Mannie Fresh’s space bloops paired with the Hot Boys’ colorful bars were just too infectious to be ignored.
But by the time “Shine” got the single treatment, cracks were beginning to form in the CMR foundation. Juvenile and B.G. had gone AWOL, leaving the label to drop a video for the “Shine (Remix),” featuring a non-Hot Boy lineup. Sure, Mack 10 and Mikkey Halsted did their thing, but there was nothing like that Hot Boys chemistry—even if this was the beginning of the end for the group. –Andrew Barber
Listen: Lil Wayne, “Shine” [ft. Hot Boys and Mannie Fresh]
Sqad Up: “Oops” [ft. Lil Wayne]
While New Orleans rappers competed for a piece of the scene after the Hot Boys breakup, Lil Wayne was aiming for something bigger: NYC. On “Oops,” off the first Sqad Up tape, Wayne effortlessly repurposes Tweet’s sultry “Oops (Oh My)” with chillingly descriptive punchlines like, “In ya tummy where the Semi would go/And I pull the trigga right after I whisper ‘gimmie ya coke.’” And in the last minute, Wayne calls out New York DJs like Kay Slay and Funk Flex to recognize the South and its new leader. “Oops” is an early peek at Wayne’s blueprint for future mixtapes, bending popular beats to his will and crowning himself king whenever he feels like it. –Nigel Washington
Listen: Sqad Up, “Oops” [ft. Lil Wayne]
B.G.: “Ride or Die” [ft. Lil Wayne and Juvenile]
With a verse sandwiched between fellow Hot Boys B.G. and Juvenile, a then-15 year old Lil Wayne made it clear on “Ride or Die” that he is not a normal rapper. His voice here is meeker than the cigarette-stained one we’ve all come to know, but the way he uses his thick New Orleans accent to rhyme nearly every syllable is an indicator of the alchemy that was to come. I’m not sure who else could rhyme “windows closed” with “stay on the floor” while articulating a quest for revenge that involves a puddle of blood too deep to swim through. –Millan Verma
Listen: B.G., “Ride or Die” [ft. Lil Wayne and Juvenile]
Lil Wayne: “Snitch”
Tha Carter was preceded in early 2004 by The Prefix, a mixtape where Wayne—who has “Lucky Me” tattooed on his neck and lyrics from that song on his leg—tries his hand at an array of beats from Jay-Z songs. While it would take until 2007’s “Dough Is What I Got” for hip-hop to really process that Wayne had replaced Jay atop the food chain, in ’04, Wayne was already improving the blueprint. “Snitch” is Wayne’s sinister variation on Jay’s circa-Black Album, Young Chris whisper-flow mode: dipping in and out of conspiratorial asides, taking glee in the fusion of pop production and swaggering gun talk. The third verse in particular is a master class, the final 12 bars hammering the same rhyming syllables before it ends in a vicious anti-climax: “Shhhhhhhh.” — Paul A. Thompson
Listen: Lil Wayne, “Snitch”
Lil Wayne: “Get Bizzy” [ft. Gudda Gudda]
Lil Wayne’s greatest Auto-Tune stuff uses the tool for passion and super leaned-out flexing. With “Get Bizzy,” Wayne punchlines that seem pretty standard on the page (“Mama said knock ya out, money made me block ya’ out”) become all-timers through his muddy and distorted delivery. He does this on the beat for V.I.C.’s “Get Silly,” a snap-rap club classic that he warps into a foggy smokers’ joint off a Screw tape, with how thick the vocal effects are and how he sounds like he’s trailing off after every bar. Wayne made the Auto-Tune pop, not the other way around. –Alphonse Pierre
Listen: Lil Wayne, “Get Bizzy” [ft. Gudda Gudda]
Lil Wayne: “Dough Is What I Got”
Zone out long enough to “Dough Is What I Got” and you’ll forget that Jay-Z even recorded that flabby Kingdom Come single on this beat as part of his return from retirement. When you get a beat from Just Blaze at his peak powers, turning up the dials on everything and letting the drums rip, you gotta come with that same energy, and Lil Wayne lands on a labyrinthine scheme in the first verse, taunting his competition just a little when he says he’s LeBron to Jay’s MJ. It was a beat jack so crushing that it allegedly made Jay-Z take a long walk, then stare at himself in the mirror and ask, “Are you sure you still got this?” –Mano Sundaresan
Listen: Lil Wayne, “Dough Is What I Got”
Lil Wayne: “Fuck tha World”
Despite having been a rapper for nine years, and despite having been a successful one for over two, when Lil Wayne’s debut album, Tha Block Is Hot, came out in 1999, he was still just a kid. “Fuck tha World” is a harsh reminder of that. Freshly 17, the pride of Hollygrove runs through a laundry list of grievances that were gnawing at his mind, trading his typically boastful bars for tenderness and vulnerability. His step-father, Rabbit, who acted as his father figure, had recently been shot and killed; Wayne’s first child had been born a year before; and he was responsible for keeping his mother’s lights on. This song isn’t the result of teenage angst—it’s the sound of someone carrying far too much on his shoulders. –Millan Verma
Listen: Lil Wayne, “Fuck tha World”
Lil Wayne: “I Miss My Dawgs”
In the early 2000s, Lil Wayne, as Cash Money’s last Hot Boy, was tasked with having to graduate from the party-starting golden boy to a young man asked to keep a flailing empire alive. On “I Miss My Dawgs,” from 2004’s Tha Carter, Wayne masterfully expresses the weight of that responsibility and dedicates his verses to the three Cash Money escapees (B.G., Juvenile, and Turk). He heightens the poignancy, at the end of his verses to B.G. and Juvenile, when he grunts, “I miss you and I know you missing me.” In essence, the song is a eulogy for one of rap’s greatest runs, from the mouth of someone who helped facilitate it, painfully accepting he’ll never get it back. –Lawrence Burney
Listen: Lil Wayne, “I Miss My Dawgs”
Lil Wayne: “Cannon”
Surprised there isn’t more Dedication 2 on here? The voting committee observed that while it’s still one of Wayne’s best, and was a key part of the run that elevated him to the Best Rapper Alive convos, it functions better as a straight-through listen than a collection of songs that can be singled out from the tracklist. There are a couple exceptions, though. “Cannon” is undeniable. The beat, peppered with producer Don Cannon’s DJ tags, hits like a ton of bricks. And Wayne makes slight work of it. Beyond the knotty wordplay, it’s all about the linguistic acrobatics he pulls off here: how he punctures the beat with those sticky, staccato phrasings of “sick” and “spit” and “vomit,” and his pronunciation of “MY-yo-nnaise” to make the rhyme work. –Mano Sundaresan
Listen: Lil Wayne, “Cannon”
Lil Wayne: “Lights Off”
There’s a violent undercurrent in Lil Wayne’s life, even if you would be hard-pressed to consider him outright menacing. The gun he got caught with by the hip-hop police on a tour bus in New York led him to have to serve eight months out of a 365 day sentence; at 12, he shot himself in the chest after his mom said he couldn’t rap for Cash Money Records, an incident he would later classify as a suicide attempt. It would behoove you to listen to “Lights Off,” the best song on Wayne’s debut, Tha Block Is Hot. Even at the young age of 17, he’s rapping about being a gun-toting freak, a boy looking at Tony Montana’s final scene in Scarface for the first time. Is Wayne a shooter? Probably not. But he is a boy attempting to be a man, in the shadows of a Southern masculinity that’s been indoctrinated into him since he was a kid. Guns haven’t always been useful for Wayne but it’s a protector, a shield for him as a boy forced to raise himself up by his comically large bootstraps. –Jayson Buford
Listen: Lil Wayne, “Lights Off”
Lil Wayne: “10,000 Bars”
The provenance is not really the point. Technically the seventh and final Sqad Up mixtape, the 35-minute exorcism more commonly known as “10,000 Bars” was allegedly a purging of the notebooks Wayne was determined to leave behind forever as he pivoted to composing songs in his head. Whether or not that’s literally true, he raps—viciously, nimbly, with an endlessly regenerative energy—over 26 different beats, and in nearly twice as many flows, he flits between close studies of his influences’ styles and whole-cloth creation. Though he pitched it as the end of one era, it was really the Big Bang for another, the beginning of the mercenary, chaos-agent streak that would make him that rarest of things: an artist on the cutting edge of his genre who also dominates the pop chart. –Paul A. Thompson
Listen: Lil Wayne, “10,000 Bars”
Lil Wayne: “Upgrade”
What better way for Lil Wayne to submit another entry into a strangely personal, “Hot N Cold” type relationship with Jay-Z than hopping on the beat of Hov’s collaboration with then-girlfriend Beyoncé “Upgrade U?” The palace intrigue of rap’s upper echelon aside, the jubilant production that usually was reserved for Beyoncé’s vocal runs is ripe for Wayne’s freewheeling style. His buoyant, staccato raps bounce around in the beat’s negative space like supercharged electrons as he rattles off references to Anita Baker, Angelina Jolie, and Apollo Creed, crafting a bizarro world version of jaunting, truncated bar construction employed on the original version. And if the odd subliminal aimed at Jay-Z slips out at the end, it’s almost to be expected considering his chuckling intro: “I love this shit/So let me talk my shit, ‘nah mean?” –Matthew Ritchie
Listen: Lil Wayne, “Upgrade”
Birdman & Lil Wayne: “Stuntin Like My Daddy”
By 2006, Wayne was no longer playing second fiddle to Juvenile or BG; he was a full blown star, inching closer to true A-list status. Birdman’s profile as an executive also continued to grow—especially as he had survived the loss of his biggest artists and key producer and, through Wayne, found a new lease on mogulhood.
Instead of rushing to release the long-awaited Tha Carter III, Wayne got with his non-biological dad to release Like Father, Like Son—a bit of a hidden gem in the Cash Money catalog. “Stuntin Like My Daddy” was the monumental lead single, and it accomplished everything it set out to do: let Wayne make a lyrical hit record without Baby getting in the way. And while Wayne does most of the heavy lifting here, as on the album writ large, Birdman does add the perfect complement. “Stuntin’ Like My Daddy,” brought out the best out of both Baby and Weezy, without trying too hard – and likely sold a whole lot of Yamaha V-Stars in the process. –Andrew Barber
Listen: Birdman & Lil Wayne, “Stuntin Like My Daddy”
Lil Wayne: “I’m Me”
Imagine for a moment if Tha Carter III began with “I’m Me” instead of “3 Peat,” as was intended before the former leaked. It would’ve made it feel biblical, Wayne kicking off the record that put him on the top of the world with a song that unabashedly celebrates rap music as a form (and compares the album you’re about to hear to the New Testament). On one level, “I’m Me” is a State of the Rap Union, opening with the smugly sighed, “Un-fucking-believable! Lil Wayne's the president.” But it’s really just Wayne telling us he loves this shit in as many creative ways as possible. He’s married to the “crazy bitch” like Keven Federline. He wants to rap until he’s literally shitting himself. Then there’s the chorus, so simple yet defiant: “I’m ME.” I don’t know how this can’t get you fired up. –Mano Sundaresan
Listen: Lil Wayne, “I’m Me”
Hot Boys: “Block Burner”
You can’t forget that Lil Wayne was a child star. It’s fashionable to focus on his explosive, relentless run in the mid-2000s, but doing so to the exclusion of his early work is to miss the point entirely. 1997’s “Block Burner,” from the Hot Boys’ debut album, is startlingly great, an example of Juvenile’s influence on young Wayne’s career. However, where Juve was a gruff, bluesy soldier, Wayne was more melodic, more nimble, loquacious even at this early age. Here he sounds as clean as Rakim and raps in legato a fusillade of bars that sound as cool as a cigarette after sex. Just 17 at the time Get It How U Live! was released, Wayne is the greatest child star of the past 30 years of music; the only reason why we don’t think of him as a child star is because Black boys aren’t allowed to be considered kids in the eyes of white America. –Jayson Buford
Listen: Hot Boys, “Block Burner”
Lil Wayne: “Go DJ”
Before Lil Wayne’s galactic ascension in 2004, there was the growing fear that the New Orleans rapper’s star was dwindling amid a Cash Money Records that had been all but deserted. Another prodigal son burned out far too early by circumstances unforeseen, as the subsequent follow-ups to his blistering debut Tha Block Is Hot failed to live up his own standard commercially (and qualitatively). Enter “Go DJ,” the purest encapsulation of the formula that would propel Wayne into a new stratosphere over one of Mannie Fresh’s best beats: a banging hook that echoes off the walls of clubs and basketball gyms (upcycled from a 1997 U.N.L.V. track), audacious declarative statements (Oh, to be the “hottest nigga under the sun”), and a barrage of bars that leave you with a stank face. The mutated synths and alien beeps place Wayne in a spaceship flying high over rap’s earthbound underlings, where he’d remain for the rest of the decade. –Matthew Ritchie
Listen: Lil Wayne, “Go DJ”
Lil Wayne: “Mo Fire”
After years of honing his craft with beat-jacking mixtapes, a new chapter of Lil Wayne opened in the mid-2000s. He was more poised, more sure of his own power, and began radiating an aura that was irresistible to a generation of fans whose childhoods were spent watching him evolve into this new form. Few songs from his catalog reflect that effortless coolness like “Mo Fire,” from 2005’s Tha Carter II. The track creeps along, moving at the speed of someone who’s enjoying a euphoric weed high, and, with the help of an uncredited Caribbean vocalist, he fully leans into the Bad Man aesthetic. If there’s a song that perfectly reflects Tha Carter II’s artwork—Wayne in black and white, shirtless, dreads hanging while he leans back onto a Rolls-Royce Phantom—it’s this one. –Lawrence Burney
Listen: Lil Wayne, “Mo Fire”
Freekey Zekey: “Beat Without Bass” [ft. Lil Wayne and Jha Jha]
Wayne is from Hollygrove, and while his dominance in the 2000s was taken as both a cause and symptom of rap’s power balance shifting south, there were times when it was undeniable: He wished he was from Harlem. On Dipset-extended universe cut “Beat Without Bass,” Wayne is now inheriting two beefs that Cam’ron was pan frying: Nas and Jay-Z. The result? Wayne stakes his claim for rap superiority, making these old rappers look in the mirror with anxiety, maybe even shame. The Timbs and the Myspace profiles and the ringtones and the Canal St. tapes blurred together in a perfect little bit of alchemy. –Jayson Buford
Listen: Freekey Zekey, “Beat Without Bass” [ft. Lil Wayne and Jha Jha]
Lil Wayne: “La La La”
Like most people from Louisiana who no longer live there, Weezy is always looking for an opportunity to tell people how much he loves it. So it feels right that the sweetest song he’s ever recorded isn’t about a lover or weed or even Baby. “Born in New Orleans, raised in New Orleans, I will forever remain faithful, New Orleans," he raps over a “Chopsticks” two-finger piano chord sampled from the New Birth’s “You Don’t Have to be Alone.” Also pulled from that pretty obscure record: a chirpy “la la la” melody that, pitched up and skipping over the drum beat, makes Wayne’s memories of biking through Hollygrove hiding crack in his mouth (“I hope it don’t dissolve”) feel as nostalgic as his memories of getting a scooter for Christmas and rocking a Saints Starter jacket. –Sadie Sartini Garner
Listen: Lil Wayne, “La La La”
Lil Wayne: “Georgia… Bush”
After Hurricane Katrina tore through New Orleans, Wayne moved to Miami. Rapping from afar, his peak period is littered with references to his hometown that are at turns pained and defiant; one thinks of him insisting, on Da Drought 3, that “They tried to make a brand-new map without us… And no matter how you change it, it’ll still be ours.” His flip of Ludacris and Field Mob’s “Georgia” is the searing, soulful explication of his rage at the administration that flooded the city. There’s the droning, atonal hook (“We from a town where/Everybody drowned”), the indignance over structural problems that had only worsened since 1965’s Hurricane Betsy, the simple relaying of stories from those who lived through the levees and “heard explosions.” There’s also what is the most memorable, most chillingly plainspoken passage of this period in Wayne’s work: “The white people smiling like everything cool/But I know people that died in that pool/I know people who died in them schools.” –Paul A. Thompson
Listen: Lil Wayne, “Georgia… Bush”
Lil Wayne: “Who Wanna”
As Lights Out gave way to 500 Degreez, Lil Wayne was no longer the cute child rapper; he was growing up and struggling to find his footing in a fast-changing business. He was still around, but would be overshadowed whenever Juvenile decided to show his face—and he couldn’t go hit-for-hit with the Big Tymers. But in 2004, something changed, and Wayne transformed into the goblin we know now. Once he proclaimed he was the “best rapper alive, since the best rapper retired” people started paying attention, whether they believed him or not.
Tha Carter revealed a new artist—one who could make hits and compete lyrically with not just his labelmates, but hip-hop’s elite, like his idol Jay-Z. C1 has been largely eclipsed in the public imagination by its Carter successors, but remains the most upbeat and bouncy of the series. “Who Wanna” is its mission statement, with Wayne sending shots at all detractors, doubters, and non-believers. “Who Wanna” is perhaps the best example of a C1 song that hits Wayne’s sweet spot: perfectly meshing his past sound (futuristic New Orleans bounce) with the lyrical chops and catchy hooks that would define the next six years of his career. –Andrew Barber
Listen: Lil Wayne, “Who Wanna”
Lil Wayne: “Lil’ One” [ft. Big Tymers]
Lil Wayne is standing on a nondescript street corner somewhere in New Orleans. Business is slow, and he’s desperate to find his next hustle. Up walks Baby, a big-time pimp and dealer from around the way, and they meet eyes. “I been peepin’ ya’ lil’ ass, I see you grindin’ and shit,” raps an impressed Baby, like he’s searching for new recruits for his street mentorship program. An overly eager and headstrong Wayne, clearly schooled on the hip-hop storytelling cuts of the ’80s and ’90s, gasses him up right back: “I been peepin’ you, too, nigga I see you shinin’ and shit/And you don’t even know how long I been tryna’ find me a brick/To make it flip and take the chips and go buy me a whip.” I could quote the whole damn song. “Lil’ One” is that good, as the eventual Like Father, Like Son collaborators size each other up and go line-for-line. The story ends with Birdman putting Wayne onto game in the car, and you can imagine his lavish rise and tragic, hubristic fall without them even saying it. It could be a conversation straight outta The Wire. –Alphonse Pierre
Listen: Lil Wayne, “Lil’ One” [ft. Big Tymers]
Lil Wayne: “Live From 504”
Even back then, it was clear that Da Drought 3 was the future: 100-plus minutes of rap at its most free-wheeling and postmodern, on which Wayne chews up the industry and spits it out, dissatisfied. If you believe that words are the most powerful things in the universe, then the 24-year-old is at the height of his over a beat jacked from Young Dro’s “Shoulder Lean.” Here he pantomimes chaos with the utmost control and lets loose a handful of all-time great one-liners: a morbid Ritchie Valens nod, a half-hearted anti-drug PSA, a line that zaps my synapses some 18 years later (“I gets hotter by the tock/Before I sizzle to death, I just tell the clock, ‘Gimme a sec!’”). Having downloaded the tape on my slow-ass Ethernet hook-up, I remember feeling alive with possibility, like if you strung together certain words in just such a way, you could restructure the universe. –Meaghan Garvey
Listen: Lil Wayne, “Live From 504”
Lil Wayne: “On My Own” [ft. Reel]
It’s widely accepted that Lil Wayne had one of rap’s greatest runs, that he got to say the culture’s heaviest phrase and have it feel right: I am the best rapper alive. Usually, that’s considered to be the time period between Dedication 2 and Dedication 3 when he perfected his superstar persona and managed to flood the e-streets and radio airwaves at the same time. But there is part of me that actually believes Wayne was at his creative peak on 2004’s Tha Carter, where the Cash Money little brother with a chip on his shoulder collides with the looser, throne-craving supernova, ready to burst.
Tha Carter was Wayne’s last full ride with Mannie Fresh, even though neither of them really knew it at the time. The album marked the culmination of a truly great partnership, with Wayne no longer following Mannie’s lead, but the producer meeting the rapper where he was at. “On My Own” is the best example of their connection, with Mannie’s shimmering bounce crackling like battered chicken in hot oil and Wayne showing his relentless desire for the crown. In an unpredictably groovy rap-sing, Wayne reflects on his past, throws the Hot Boys under the bus (“Out of all the Hot Boys, she say I’m the coolest”), and tells the hip-hop world to get with it or get left behind: “So roll the carpet out/’Cause you fuckin’ with a nigga from the royal South/See, you’re either in or you’re out.” It’s the hungriest rapping from the poster boy of hungry rapping. It’s also perfectly fitting for Wayne that his highest high comes not on a radio hit, a high-profile beat-jack, or even on the culturally defining Tha Carter III, but just locked in with Mannie Fresh on Tha Carter, Track 8. –Alphonse Pierre