While not an example of his best lyrics, the song has become a staple of every celebration in black America and an early signifier that Wayne would be a star. 15: ‘Tie My Hands’ (featuring Robin Thick) Wayne rapped a lot about the impact of Hurricane Katrina and the Bush Administration.
Sometimes he did it brazenly, but “Tie My Hands” is the opposite, thanks in part to a feature from Robin Thick. His voice is restrained but hopeful, and a great counterpart to Wayne’s (at times frantic) grief.
He was at his most convincing in this mode on They Carter II, on which his fame and power were in perfect balance. 13: ‘This Is The Carter’ Because the collaborations between Wayne and Annie Fresh were ultimately fewer than a lot of people hoped for, the highlights have come to age like fine wine.
In some ways, he did, though the song would more or less mark the end of his professional involvement with Many Fresh for years to come. But the fact that it works and is inherently charming is a testament to the charisma that found Wayne living up to the best rapper alive” boast when They Carter III was released.
For others, it was a moment of Wayne’s noticeable transformation into a more diverse, freely associative rapper. 9: ‘We Takin’ Over’ (DJ Khaled, featuring Akin, TI, Lil Wayne, Rick Ross, Bird man and Fat Joe) Another DJ Khaled song ranks higher than this one, but the original “We Takin’ Over,” and Wayne’s subsequent freestyle over the instrumental, was indisputable proof that, when he said he was the best, he was right.
8: ‘Right Above It’ (featuring Drake) “Right Above It” came at a specific moment in time in Wayne’s career: his unopposed run as the king of random was drawing to a close, and he was about to start his infamous imprisonment at River’s Island. Kanye was poised to release My Beautiful Dark Twisted Fantasy, and Drake was getting bigger by the day.
“Stunting’ Like My Father” is so big, its reputation will probably outlive the feud that eventually undid their collaborative partnership. It opens up with the bombastic and melodramatic “3 Peat’,” as Wayne runs his victory lap throughout the rest of the album.
‘Mr Carter’ isn’t just two titans trading bars over a classically-chipmunked soul sample, however, it’s one greatest all-time baton passes and endorsements. It’s lyrically sparser than a lot of what Wayne was known for at the time, but the trade-off was one of his most earworm-y hooks and biggest crossover singles ever.
‘Fireman’ and the majority of the singles off They Carter were smash hits, but for a few months you couldn’t go anywhere in America without hearing “Lollipop.” 2: ‘Hustler Music’ For those among Wayne’s fans who consider Carter II to be his crowning achievement, “Hustler Music” is perhaps most representative of a “they don’t make ‘em like this anymore” beat that showcases the confidence of Wayne’s flow.
1: ‘A Mill’ With “Lollipop,” Wayne crafted one of the biggest crossover singles ever, establishing the complete hip-hop domination he’d been talking about for years. The beat is an instant classic that’s a perfect slam dunk for Wayne’s unmatched charisma.
1 single on the Billboard Hot 100 -- Wayne's They Carter III sold over a million copies during its opening week. I ain’t tripping’ on nothing, I’m Pippin’ on something.” Wayne takes the time to lament on an old relationship, all while calmly celebrating his new freedom.
The track originally appeared on the mixtape No Ceilings, but quickly earned its spot on I Am Not A Human Being. The slower warped beat was an updated, unusual take for the rapper, but telling of Wayne’s growth by 2010.
With the help of the ever-smooth Bobby Valentino, Wayne delivers a slow jam for the ladies, all while emasculating all the cops who have ever done him wrong. Complete with a cultural reference to Rodney King, Wayne lays back on this one, making it one of his smoothest songs, and another testament to his witty metaphor skills.
After the catastrophic 2005 Hurricane Katrina swept the south, the rapper took aim at President George W. Bush, who was criticized for slow response to the natural disaster, and as Wayne puts, “let em kill all of our troops.” Long before the lawsuits, the accusations, and the deteriorating label, Bird man and Wayne ruled the south.
After Lil Wayne proved himself as the best out, he started working on an emcee worthy enough to pass the torch. By “Believe Me,” Drake was fairly established, but the Weezy affiliation still seemed connected to his name, and parts of his flow still seemed a little borrowed from his predecessor.
The first thirty seconds of “I’m Me” are basically a killer compilation of all the best Cash Money affiliates’ adults and assertions, from the Bird man bird call to the “it’s Cash Money Records man, a lawless gang.” Then what ensues is the closest a rap song can get to a power ballad -- a song with Wayne showing off as hard as he can go on a laid-back flow. He put it best when he said, “This is They Carter III, the New Testament.” The song spans a full five minutes, with Wayne not backing down once, trading in a faster flow for tact and lyrics, and flexing his iconic use of double entendres more than once.
The cut came from the first-ever Cash Money Records joint album, marking a time when the label was at its peak, before the lawsuits and online back-and-forths. Catching up on a beat that’s a bit more melodic than Weezy’s usual portfolio picks, “Hustler Music” is the rapper's own version of a more classic New York sound.
The combination makes for a Weezy track that delivers life advice and lessons in a way that’s a little softer than some others. In a showcase of a slightly more sentimental side, Wayne delivers one of the most relatable songs of his catalog -- a somber, cutting, and simple ode to lost friends and family, and fading friendships and relationships.
On any streaming platform, the comments below “I Miss My Dawgs” are flooded with messages to lost connections and relatives, a testament to the way the track hit with listeners. For a generation of fans, this debut solo single was the first track they heard from the scrappy 17-year-old Atlanta rapper.
No longer just a hype man for the older guys on the label, a much-younger Lil Wayne proved his prowess with this classic track. Wayne’s voice is as raspy as ever, and the video shows him baby-faced, still surrounded by the big kids on the label.
Over the iconic “Swag Surf” beat, Wayne begins with a flow similar to the original, but adds the exclamation points we expect from him at this point: clever wordplay (“watch me shooting to the bank, I’m a money pistol”), nearly four different flows on one track, and a consistency that lasts for the entirety of the five-minute song. At the height of the Auto-Tune movement arose the ultimate Auto-Tune masterpiece: “Lollipop,” an iconic Lil Wayne track based around an incredibly unsubtle innuendo.
The song and video immediately became a major mainstay on the spin cycle at TRL -- at a time when that meant a lot -- with cameos from R. Kelly and a very young Toga. Adding to its early 2000s glory, the track also became the #1 selling ringtone of 2008, bumping out of millions of flip-phone speakers across the nation.
The pressure that surrounds dropping a track entitled Best Rapper Alive” is obvious. Switching effortlessly between at least two different flows, Wayne saunters over the DJ Khaled beat, adding “fucking” to the list of words the F in Weezy F Baby stands for.
“Young money militia, and I am the commissioner, you don’t want to start Weezy causes the F is for finisher.” Wayne absolutely destroys the militaristic beat, pulling back on speed at points, only to emphasize absolute speed and dominance in his bars moments later. At one point, he spits “Ain't nobody fucking' with me, man /He-man, ski mask, spending' next week's cash, he fast, and I don't even need a G pass,” a play on words so casually brilliant only “the best rapper alive” could pull it off.
“Let The Beat Build” is a concept track at its core, a swaggering soulful rap ballad that takes one of the most recognizable samples of all time and pairs it with the then best rapper alive.” Its brilliance is -- as almost always -- in the way that Wayne can match, and then add, to a beat. Then, with only about a minute left, he dances off of it, quickly and cunningly dropping some of his most explosive bars, almost as if to prove it’s not just the Deeply and Kanye West produced beat that’s leading this track.
You'll notice that, as a result, they skew toward my favorite era of Lil Wayne, 2004-2009, at the expense of the present and the more distant past. But there are a few reasons for this: Wayne's output has slowed considerably from that frenzied era, and, besides, a lot of his new stuff hasn't had time to settle in the same way.
As for the older stuff, I'm of the opinion that Wayne has steadily gotten better over his career. So you might not want to use this list as the definitive guide to understand the entire arc of Wayne's career.
But I promise that if you listen to these 100 songs, you will walk away happy with what you heard. They float against the stars, painting weightless vapor trails, dipping and diving in balletic sine waves.
It's beautiful, this blend of technology and the void; the image often comes to mind when I hear the otherworldly synth beeps that lead into LilWayne's “Lollipop.” If people know one track of Weezy's, it's this one, and their impression of him is as it should be: He is an otherworldly, mischief-making, sex-crazed sprite, popping bottles and careening through hip-hop as he remakes it in his image.
I can't claim some objective version of the Lil Wayne canon exists in these songs. But the beautiful thing about Lil Wayne is that everybody has their own idea of what constitutes the official record.