Conceptually, the music is never out of reach. Lil Wayne is an artist whose work can be enjoyed immediately, without explanation. But that's kind of the point of what makes "Lollipop" so good. 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. It shouldn't work that way, but it does.Īgain 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. The pussy in Wayne's mouth has him lost for words, indeed. 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. For all its apparent simplicity, it is a swirling world of chaos, where rules collapse under its wily sonic logic. No matter how many times you listen to "Lollipop," it retains an enduring sense of the unexpected. And yet it also sounds sublimely pretty, the promise of technology in the first days of a dawning digital era. It sounds so ugly, the belching id of the club in the last days before the recession. The spaces in those synths are just too cavernous, and the straightforwardness is just too confounding. "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. And so "Lollipop," the pinnacle of Wayne's weirdness, is his best song. As the best rapper alive, Wayne was uniquely positioned to usher melody and Auto-Tune into rap's mainstream. It's this version that went beyond proving Wayne's brilliance to lay the blueprint for so many ensuing trends in pop music. But when it comes to the historical record, weirdo Weezy gets the edge. 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. 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. What do rappers do, if not exactly this? And: Who ever heard of a rapper doing anything remotely like this? 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. And in a nice twist of Martian poetry, the weirdest Lil Wayne song is also the most popular Lil Wayne song. It sounds like a party about to fall off the edge of the Milky Way. It sounds like a robot love story in space. 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'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." They float against the stars, painting weightless vapor trails, dipping and diving in balletic sine waves. 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. But I promise that if you listen to these 100 songs, you will walk away happy with what you heard.ġ. So you might not want to use this list as the definitive guide to understand the entire arc of Wayne's 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. As for the older stuff, I'm of the opinion that Wayne has steadily gotten better over his career. 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. 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. Everyone has their favorite Lil Wayne songs, and these are mine.
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