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Lil Wayne's "Prostitute 2" Is Better Than '808s and Heartbreak'

Remembering the forgotten but pioneering Auto-Tune classic.
Illustration by Michael Alcantara

Day 252: "Prostitute 2" – leaked/unreleased, 2008

In the summer of 2008, Kanye West returned. He had cemented his role as the shutter-shaded standard bearer for rap's future the previous fall, defeating 50 Cent in a much-hyped if semi-contrived sales battle, imagining hip-hop as a neon dream world where Daft Punk and Steely Dan and Chris Martin were all dancing in the flashing lights. It was larger than life, it was Hollywood on ecstasy, it was widescreen stadium status shit. The tour was called Glow in the Dark. Rihanna was the opener. And then Kanye's mother had died, and he had disappeared from the public eye—only to return that summer on a song.


The song was called "Put On," by Young Jeezy. Kanye had the third verse, and it remains one of the most important statements of his career. Kanye was previously content to let his interactions with Auto-Tune happen in the context of getting T-Pain to sing about the good life. But this was something different. It was elemental. It was Auto-Tune in a whole new context.

"I lost the only girl in the world that know me best / I got the money and the fame, and that don't mean shit / I got the Jesus on the chain, man, that don't mean shit," Kanye howled, rattling off grievances with people who still owed him checks and girls who still owed him sex while stewing in the loneliness of fame. Auto-Tune was a tool for singing about partying, about popping bottles, about falling in love with a stripper. It wasn't sad, right?

In that verse, Kanye West laid the blueprint for what would become 808s and Heartbreak and arguably the next decade of his career as a public figure, a martyr to the cause of fame. And that blueprint, of course, has gone on to be seen as wildly influential. If you have no 808s and Heartbreak, the thinking goes, you have no Drake or Future or whatever else sad boy rap crooning is happening these days. And that is, to some extent, true. Drake's producer 40, for instance, credits 808s directly for the sound of Drake's breakout project So Far Gone. There is no denying that the album was a pivotal turning point for Kanye. But the idea that it invented the idea of Auto-Tune as an artistic tool rather than a frivolous one is ridiculous.


For that, let's return to the other biggest rapper in the world from 2007 to 2008, Lil Wayne, and his parallel timeline.

In 2007, in the midst of his legendary mixtape tear, Lil Wayne began playing with Auto-Tune. It began to crop up on odd verses, and it eventually made its way into entire songs, including a few destined for the original version of Tha Carter III. That version, of course, leaked, and among the songs that spilled into the ether never to be formally released was one called "Prostitute Flange," ostensibly dedicated to Wayne's girlfriend at the time, Karrine "SupaHead" Steffans.

"Prostitute Flange" is one of the weirdest love songs ever made, although by the weirdo standards of 2017 it might sound predictable, as groundbreaking music often does. The hook goes "I wouldn't care if you were a prostitute / and that you hit every man that you ever knew." Compared to Wayne's usual approach to romance on songs ("get money, fuck bitches"), it was a revelation. Here, Wayne suggested there was a jersey with his name on it at the top of the arena because he was willing to give up the game for this girl. All he asked was that she keep no secrets, that she never lie, that she keep it real. But what's love if not trust?

It was a song with a kind of emotional honesty that Wayne rarely showed, brought out by the careening power of Wayne's singing in Auto-Tune, which he did for six minutes, including four minutes of what was essentially an outro of him gurgling. It was a beautiful improvisation that predicted basically everything Lil Wayne would build his sound around for the next decade. It has gone on to become a cult classic; in 2013, Complex named it the 12th best Lil Wayne song of all time.


By the time Tha Carter III was actually ready to come out, Wayne had moved on to a different, more playful Auto-Tune single with less unguarded honest and much sharper songwriting: "Lollipop." In the spring of 2008, it hit number one on the Billboard Hot 100, just in time for the album release. Wayne had the biggest album in the country (one of the biggest of all time) and the biggest song, and that song was slathered in Auto-Tune. If there were ever a moment to start taking the technology seriously in a way that T-Pain and Ron Browz couldn't ask us to, it was then.

Which brings us back to 808s and Heartbreak. After "Put On," Kanye began rolling out the album's singles: "Love Lockdown," "Heartless," etc. There was even a song with Lil Wayne, "See You in My Nightmares," where Wayne embraced the howling, pitch-corrected chaos of the album to nearly unintelligible effect (while I love Wayne, I'd argue he continued his tradition, started the year before on "Barry Bonds," of showing up on the worst Kanye singles). While the popular narrative now is that 808s and Heartbreak was widely hated and later discovered as an influential stealth classic, as far as I remember it got pretty positive reviews while spawning two of Kanye's biggest singles ever, and everyone at the time basically agreed it was obviously going to be incredibly influential. That's because it capitalized upon a zeitgeist that was clearly already underway, courtesy of Lil Wayne. You know what I mean, yeah? If you don't then I'll explain.


In the midst of the whole 808s frenzy (for those complaining about the Life of Pablo rollout, Kanye has never been one to shy away from maddeningly overextended hype cycles), another Lil Wayne leak quietly surfaced on the rap blogs, soon to be swept away into the category of minor Wayne leaks to which nobody paid attention. But, dear reader, I paid attention.

The song was a more carefully mastered and fully imagined rework of "Prostitute Flange" that the blogs dubbed "Prostitute 2." As far as I was concerned, it delivered on every promise Wayne had ever made. It had the emotional vulnerability that came from using the effect that the original and "Lollipop"—and "Put On" and 808s—hinted at, but it was also just a better song. He pushed the traces of the filter that were in the original to a more extreme endpoint, finding forgotten pockets of emotion in the curlicues of his syllables as they bent and contorted in unexpected directions. He found sounds that no human had previously uttered. And he didn't sound like he was noodling around on an idea anymore; it was an actual, structured song.

There's a part in the original "Prostitute Flange," right after the jersey in the rafters part, where Wayne sings "every time I see you I get asthma baby" and then acts it out. But in the follow-up, he sings slower, and the pause is longer. He breathes in like he's really gasping: "every time I see you I get asthma baby / like ah-heuhhh! That's my baby." It transforms a line that might have flown over your head in the original into an inflection point, a moment of serious reflection. It's one of those places where, much like when Wayne chomps to act out eating his opponents on "Stuntin' Like My Daddy," Wayne's total control of a track as a playground for sounds shines through.


Hearing that gasp for the first time opened up a whole new dimension of my understanding of Wayne. In that gasp and its pillowy Auto-Tuned surroundings was basically everything I'd ever wanted from music. Since it was a leaked throwaway track for Wayne, I had to wait another four years, until the release of Future's Pluto, to find much more like it. But at least that point I knew it existed.

I've realized the more that I've researched this post that "Prostitute 2" never made the splash I assumed, by virtue of my thinking it was the greatest song ever, it had. It's possible it was never even meant to be a song and was in fact a better-produced and more carefully mastered outtake of the much-celebrated—if to my ears inferior—"Prostitute Flange." But I do still firmly believe that the legacy of the song, whichever version you prefer, is essential. Kanye was an experimentalist, but he was an artiste. He made a big deal about it. Wayne was experimental in an unpretentious way, and he was even more popular than Kanye, and I have to imagine that made a bigger impression on the artists like Future and Young Thug who have ultimately carried this Auto-Tuned sound forward. I will always argue for a more accurate re-revision of the revisionist history that Kanye made the technology cool. But that's really neither here nor there.

Because on top of that, I will also always argue for a revisionist history in which we remember this sidelined Lil Wayne song as one of the finest in his catalogue. And if you don't agree, well, I'll echo Wayne warbling "they'll never know you the way I know youuuuuuu" and encourage you to get to know this Lil Wayne the way I know this Lil Wayne, the best Lil Wayne.

Follow Kyle Kramer on Twitter.