The 100 Best Lil Wayne Songs

This is almost it; one day remains in A Year of Lil Wayne, which means that it’s time to start looking back on everything we’ve learned over the past year. And what better way to look back on everything than with a dang list?

There are quite a few lists of the best Lil Wayne songs floating around out there, but this is the most correct one. Why is it the most correct? Well, first of all because I spent a year thinking about the best Lil Wayne songs every single day. Second of all because it is my personal opinion, and my opinion is always right. And third of all because what is the point of a list if not to make people mad? 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.

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Everyone has their favorite Lil Wayne songs, and these are mine. 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. The list also skews toward stuff that was covered during A Year of Lil Wayne because a) I tried to cover most of the songs I cared about and b) that conveniently took care of write-ups for the list entries. 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.

1. “Lollipop” feat. Static Major (Day 364)

There’s this scene in WALL-E, the Pixar movie about an adorable robot, where WALL-E and his robot love interest EVE share a dance in space. 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 Lil Wayne’s “Lollipop.”

The best Lil Wayne song is “Lollipop.” When I first heard it, it was the weirdest pop song I’d ever heard; nearly a decade later, it still is. It sounds like a robot love story in space. It sounds like a party about to fall off the edge of the Milky Way. It sounds like an orgy on Mars. Of course it does. Lil Wayne is a Martian. And in a nice twist of Martian poetry, the weirdest Lil Wayne song is also the most popular Lil Wayne song. 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. What do rappers do, if not exactly this? And: Who ever heard of a rapper doing anything remotely like this?

There are, roughly speaking, two sides of Lil Wayne’s music: one where he’s rapping better than anyone alive and one where he’s channeling the strangest sonic impulses he can. Neither is inherently better or more important than the other—Wayne the experimentalist wouldn’t exist without Wayne the prolific spitter—and increasingly the two are converging. But when it comes to the historical record, weirdo Weezy gets the edge. It’s this version that went beyond proving Wayne’s brilliance to lay the blueprint for so many ensuing trends in pop music. As the best rapper alive, Wayne was uniquely positioned to usher melody and Auto-Tune into rap’s mainstream. And so “Lollipop,” the pinnacle of Wayne’s weirdness, is his best song.

“Lollipop” is, on the surface, perhaps the dumbest and most obvious Lil Wayne song ever made, a one-dimensional pun that never really gets any deeper and also involves the phrase “lovely lady lumps.” And yet it’s also impossible to wrap your head around. The spaces in those synths are just too cavernous, and the straightforwardness is just too confounding. It sounds so ugly, the belching id of the club in the last days before the recession. And yet it also sounds sublimely pretty, the promise of technology in the first days of a dawning digital era. No matter how many times you listen to “Lollipop,” it retains an enduring sense of the unexpected. For all its apparent simplicity, it is a swirling world of chaos, where rules collapse under its wily sonic logic. Like a dream, you can hear it a million times and come away from it with only a vague memory of the lyrics until the next time, when they immediately re-reveal their brilliant, familiar economy. The pussy in Wayne’s mouth has him lost for words, indeed. It shouldn’t work that way, but it does.

Again and again in the Year of Lil Wayne, I began to write about this song before stepping away and deciding I needed more time to do it justice. Maybe it’s just getting the top honors in this list because it was the one Wayne song I put off writing about the longest. But that’s kind of the point of what makes “Lollipop” so good. Lil Wayne is an artist whose work can be enjoyed immediately, without explanation. Conceptually, the music is never out of reach. And yet, the more you grasp at methods to explain its brilliance—which should be simple!—the more explanations prove elusive. Someone can write all the blog posts about Lil Wayne they want, rank all the Lil Wayne songs in the world, and still be no closer to communicating what is at the center of “Lollipop.” As another critic once said of the subject in question, the world may never know.