Since proclaiming himself the “best rapper alive” on his 2005 album Tha Carter II, New Orleans MC Lil Wayne has been living up the title. Lil Wayne has decades in the game, after rising to prominence in the Hot Boys, with Juvenile, B.G., and Turk on the Cash Money label. Nowadays, he stands as one of the best-selling artists of all time. As these best Lil Wayne songs show, his influence on hip-hop culture is immeasurable. During the mid-00s, you couldn’t go anywhere without hearing his free-flow, and now we’re counting down the Top 20 Lil Wayne songs. After all, it’s Wayne’s world, we’re just living in it.
25: Drop The World
Like most of Weezy’s output, “Drop the World” was legendary before it even came out. It’s the stand-out track on Rebirth, and not just because it’s one of the most verse-heavy cuts. Wayne’s ascent to the top began shortly after Eminem’s struggle with drug addiction got real. So when Em was back on the scene in 2009, people wondered when the two guys might collaborate. They’d never done so before — two of the only titans who hadn’t – and the result was an instant classic. “Drop the World” was the first (and maybe best) of the three songs the MCs would appear on together over the course of the next year.
24: 30 Minutes to New Orleans
To his diehard fans, Lil Wayne’s ascent was defined by delays and leaks. In 2007 and 2008, you could get on DatPiff, SOHH, or wherever, and there’d be new Wayne music. The leaks got him a buzz like no one had ever had. Would we get full versions of the songs? Mixed and mastered versions? For most of these, the answer was no. Maybe the most famous instance was “30 Minutes to New Orleans.” It first reared its head in a documentary called The Carter, with Wayne rapping it on a tour bus, but we wouldn’t get a full version for what felt like years.
“Georgia… Bush” is unique among Lil Wayne’s catalog, but there are few songs like it in rap, period. It’s almost like one of those times a comedian gives an amazing performance in a dramatic role. The bars are scathing and the hook is a slam dunk. What more could you ask for? Dedication 2 was one of the mixtapes that propelled Wayne to new heights between Tha Carter IV and Tha Carter III, and closing it out with this song is one of the most show-stopping moments of Lil Wayne’s career.
22: Nightmare of the Bottom
It was never an official single, but “Nightmares of the Bottom” is one of the songs that made Tha Carter IV what it was. Wayne had spent the past few years cultivating this rockstar persona, and now, fresh out of Rikers, he was debuting a new song on an MTV Unplugged session. The rockstar thing was working out. “Nightmares” has a beat that makes it feel like something Wayne could have recorded years earlier, and being sandwiched between C4’s official singles makes it feel even more standout.
Halfway through Tha Carter V, it becomes clear that the wait was worth it. The album hits the ground running, wiping away any doubt after years of delay, but by the time you get to “Problems,” it’s evident that Wayne is still among the best. He reminds you that he can still kill a hook with his flow, and it’s so slick here that it’s easy to miss just how good his wordplay is. His inflection makes it one of his most existential-feeling hooks too.
20: I Miss My Dawgs
“I Miss My Dawgs” is a poignant song for many reasons. It’s Lil Wayne at a young age, honestly and candidly addressing his falling-out with former labelmates – and he’s still on the label. It was also an early sign of the power of Wayne’s elastic voice, which could bounce from a shrill croak to a brash rasp in an instant. On 2004’s Tha Carter, Wayne already had a backstory that was making him a legend.
19: 3 Peat
The opener of Wayne’s most monumental album is huge. Over a Maestro beat, he raps his ass off for three minutes straight. On Carter III, he’d do this while also going pop in the biggest ways, getting weird on songs like “Phone Home” and taking on personas in songs like “Dr. Carter.” “3 Peat” is so impressive that it basically gives Wayne permission to do whatever he wants.
18: Money To Blow (Birdman, featuring Lil Wayne and Drake)
Together, Wayne, Drake, and Birdman recorded a number of tracks, most of them certifiable hits that ended up on Birdman projects or Wayne mixtapes that didn’t get an official release. “Money To Blow” is most emblematic of the Birdman lifestyle that brought all these guys together. It also boasts a classic Drake hook from his early days and culminates with one of Wayne’s most prophetic lyrics of all time: “We gon be all right if we put Drake on every hoooook.”
17: Make It Rain (Fat Joe, featuring Lil Wayne)
One of Wayne’s first classic features comes from era that seemingly had no end. And it’s just a hook! Wayne was always good for a hook – it’s one of the more underrated aspects of his career, and certainly an unsung skill as a featured artist. A rapper so big appearing on a track with Fat Joe was another sign that hip-hop was rapidly changing throughout the 00s.
16: Back That Azz Up (Juvenile, featuring Mannie Fresh and Lil Wayne)
“Back That Azz Up” is among one of the best Lil Wayne songs – and it’s not even his track. He only has a feature, and it’s an outro. 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. His presence alone speaks to his charisma, even though he wasn’t even a solo act yet.
15: Tie My Hands (featuring Robin Thicke)
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 Thicke. His voice is restrained but hopeful, and a great counterpart to Wayne’s (at times frantic) grief. Few rappers are tied to their city like Wayne is to his.
14: Grown Man (featuring Curren$y)
Wayne made a handful of songs like “Grown Man”: laidback without quite evolving into full-on seduction anthems. He was at his most convincing in this mode on Tha Carter II, on which his fame and power were in perfect balance. After that, he got too big to kick it like this. ‘Grown Man’ is classic not just for the beat, but for the king of chilling, Curren$y, getting a feature. He and Wayne have a storied career, but this is his only appearance on a Lil Wayne studio track.
13: This Is The Carter
Because the collaborations between Wayne and Mannie Fresh were ultimately fewer in number than a lot of people hoped for, the highlights have come to age like fine wine. “A lot more rich and a whole lot smarter” wasn’t just true on Tha Carter, it was true three times in a row. Wayne’s mumble of “finally perfect” wasn’t true yet, but the way he said it, you knew it would be.
12: Go DJ
“Go DJ” is the quintessential song of the golden age of Lil Wayne and Mannie Fresh. If you had to bring one song from Tha Carter to a desert island, this would be it. Wayne sounds hungry, like he could have rapped on this thing forever. In some ways, he did, though the song would more or less mark the end of his professional involvement with Manny Fresh for years to come.
11: Dr. Carter
“Dr. Carter” is possibly the unlikeliest success of Wayne’s career. It’s not only a concept song, which, in 2008, had largely fallen out of fashion, but it’s also exceptionally literal. On top of that, it’s ridiculous. 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 the Young Money album Tha Carter III was released. (The record went platinum in its first week and won a Grammy Award for Best Rap Album.)
For a generation of listeners, “Fireman” was their introduction to Lil Wayne; it may have been their first time seeing A Bathing Ape gear in a music video, or recognizing the Phantom on the cover of Tha Carter II by name. For others, it was a moment of Wayne’s noticeable transformation into a more diverse, freely associative rapper. With “Fireman,” it became clear just how much potential Wayne had.
9: We Takin’ Over (DJ Khaled, featuring Akon, TI, Lil Wayne, Rick Ross, Birdman 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. The sentiment of the song applied to Wayne quite literally, and “Feed me rappers or feed me beats” would be the mantra of his career-defining run.
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 rapdom was drawing to a close, and he was about to start his infamous imprisonment at Riker’s Island. Kanye was poised to release My Beautiful Dark Twisted Fantasy, and Drake was getting bigger by the day. Kane Beatz was also making some of the best beats of the era, and this was one of them. It’s one of the standout Wayne/Drake collabs that sees them being uncharacteristically jubilant but not without some venom.
7: I’m On One (DJ Khaled, featuring Drake, Rick Ross and Lil Wayne
This is one of the best, if not the best, DJ Khaled singles, and it’s absolutely vintage Drake and Rick Ross. The “DJ Khaled!” drop is almost chilling, and it would be hard to top a beat featuring these three artists at that time. But the real show-stealing moment comes from Wayne, who opens his verse with one of the best lines of his career: “I walk around the club… f__k everybody.”
6: Shooter (featuring Robin Thicke)
Wayne was always a confident and eclectic collaborator. It’s one of the things that eventually led him to Rebirth. If “Tie My Hands” is a sobering tribute, then “Shooter” is a slow, seductive build to a piercing series of moments that are quite opposite of sobering. Thicke’s best collaboration with a rapper, it’s also a staunch and awesome indictment of anti-Southern sentimentalities: “If we’re too simple, y’all don’t get the basics.”
5: Stuntin’ Like My Daddy (featuring Birdman)
Of all of Wayne and Birdman’s Cash Money Records collabs, this is the most essential. It’s got the best hook of any song they’ve made together – and probably the best hook of the era – and it features some of their most vintage verses. For mainstream fans more familiar with Wayne, it turned Birdman into a household name. “Stuntin’ Like My Daddy” is so big, its reputation will probably outlive the feud that eventually undid their collaborative partnership.
4: Mr Carter (featuring Jay Z)
Tha Carter III established Wayne as one of the most important rappers of the era. 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. Jay’s presence on the song was especially significant given the duo’s history of will they/won’t they feuding.
3: Lollipop (featuring Static Major)
T-Pain and Kanye West both got famous using autotune, but it was Wayne’s “Lollipop” that really ushered it into mainstream acceptability. Now it’s a mainstay, but “Lollipop” is still one of the era’s most memorable moments. 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 Tha Carter were smash hits, but for a few months you couldn’t go anywhere in America without hearing “Lollipop.” (Literally. It topped the Billboard Hot 100 for three weeks.)
2: Hustler Musik
For those among Wayne’s fans who consider Carter II to be his crowning achievement, “Hustler Musik” is perhaps most representative of a “they don’t make ‘em like this anymore” beat that showcases the confidence of Wayne’s flow. Even before he became the biggest rapper in the world, Wayne believed he’d made it.
1: A Milli
With “Lollipop,” Wayne crafted one of the biggest crossover singles ever, establishing the complete hip-hop domination he’d been talking about for years. If there were still any doubters, “A Milli” proved not only that he could play in the pop lane, but that he could out-rap just about anyone. The beat is an instant classic that’s a perfect slam dunk for Wayne’s unmatched charisma. On “A Milli,” he truly was the best rapper alive.
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