Kanye West and Lil Wayne Represent the Twin Poles of Art

Day 361: "Lollipop (Remix)" feat. Kanye West – Tha Carter III (Deluxe Edition), 2008

This week marked the tenth anniversary of Kanye West's Graduation, which would have been a perfect opening to talk about one of the most storied Lil Wayne verses, on that album's "Barry Bonds." But the story of that verse is that, while it was wildly anticipated as the long-awaited union of the two hottest guys in rap, it was a massive disappointment. It was probably the least hot verse Wayne dropped in 2007. It was meant to be a blockbuster moment, and it pretty much flopped. Maybe you don't feel this way. But this is my blog, and I maintain that Wayne blew it.

I also was never much a fan of Wayne's appearance on 808s and Heartbreak the next year. So I haven't written a ton about Kanye's use of Wayne in his music on A Year of Lil Wayne. Instead I've focused more on highlighting, for instance, that Kanye produced the most slept-on song from Tha Carter III and pointing out that posse cuts like "Maybach Music 2," "Forever," and "Swagga Like Us" are where Wayne and Kanye shine best as foils for each other. I think there's a reason for this, which is that Kanye, for all his talents as an auteur, for all his ability to bring out the best in other artists, is too different, process-wise, from Wayne. He's on record as saying Wayne is the "number one rapper in the world," so it's not that Kanye doesn't appreciate Wayne. Rather, I think they are simply different kinds of artists, two necessary poles of artistic creation.

Kanye is a perfectionist who continues to tweak everything he does until it's exactly the way he wants it; consider how he was still updating his most recent album even after releasing it. He approaches music like fine art, the way a sculptor might. Wayne, on the other hand, approaches music more like an athlete, with the mindset that he has practiced enough that he can deliver a professional performance under any circumstances, and, if it's not quite what he wanted, there will always be another opportunity to prove himself. He just records his verses and moves on to the next thing. I have no facts to back this up, but I would imagine the reason "Barry Bonds" is so underwhelming is that Kanye spent a ton of time agonizing over it, while Wayne probably recorded his verse in 15 minutes and then forgot about it.

Neither approach to creativity is inherently better than the other, as demonstrated by the fact that Kanye and Wayne are the two most important rappers—or, really, musical artists, period—of their generation. Both are similarly successful by commercial and critical standards (although Wayne's approach would seem to lend itself more to a singles-driven career than Kanye, whose career has been more album-driven). But their techniques are not necessarily compatible with each other, at least not when Kanye's in the driver's seat.

The moment they mesh best on a standalone track is when Wayne is in charge, on the "Lollipop" remix, and Kanye is freed of the burden of trying to make some grandiose artistic statement. Instead, the song is just a playground to noodle around in Auto-Tune and try out a bunch of punchlines. "You ain't finna murder me like everybody else," Kanye raps, to Wayne. "I'ma rap like I got some type of respect for myself." The result is some of the most impressive rapping either has ever done.

On Kanye's side, that means getting silly and weird: "Tell her, ''girl, like Doritos, that's nacho cheese' / tell her friends, 'like Fritos, I'm tryin' to lay' / I can't only have one and I ain't tryin' to wait." You can almost see the evolution from Graduation-era Kanye to post-Grad Kanye on this song, the way he leans into the Auto-Tune and the super memorable punchlines. There's a confidence and economy to his bars here that will become more pronounced on his later albums, and the singing obviously is a big development.

On Wayne's side, it means taking a song that was previously a pop playground and making the point that "Lollipop" may have featured him singing but its success in no way diminished his skills on the mic. His two verses here are some of his best and most memorable ever. First, he explains that he "just wanna act like a porno-flickin' actor." Then, he plays off of Kanye's snack theme but in a totally different direction: "I got so much chips I swear they call me Hewlett Packard / I got so much chips you can have a bag if you're a snacker." For most rappers, that Hewlett Packard line would be career-defining, but here it's just a footnote to the rest of the verse. Has Wayne ever rhymed with more complexity than on the "Lollipop" remix? I doubt it, and here are the two examples that prove it.

Number one, four bars that rhyme around the sound of the word "ointment," a word that has probably ever even made it into a song on a handful of occasions throughout history:

And then number two, perhaps the cleverest four bars Wayne has ever rapped, a total tongue-twisting funhouse ride of homonyms and syllable-level precision that doubles as a PSA:

If you've ever considered having unprotected sex, perhaps these words have crossed your mind. But I want to point out one more thing about this whole passage, which I never noticed until now because a) I am an idiot and b) I was always too busy marveling at those bars. Wayne finishes his verse with a final riff on the topic, a final coda to the entire idea of "Lollipop" as a song, as a hit, as an international, career-defining phenomenon. "So wrap it up," he declares, which is a rejoinder to that line but also funny because it is how he ends (i.e. wraps up) his verse. He completes his lines about wearing a condom, which are themselves a riff on the fact that "wrapper" and "rapper" sound the same, by telling himself to "wrap it up." That is the rare triple-decker concept pun, which you will hardly ever see in the wild. But that's what you get when you make a song that necessarily, because of the people involved, has to be epic, and set them loose. Not to be self-important but, rather, to be brilliant.

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