Remember Lil Wayne’s Song with Wyclef Jean and Akon?

Day 293: “Sweetest Girl (Dollar Bill)” feat. Akon, Lil Wayne, and Niia – Wyclef Jean, Carnival Vol. II: Memoirs of an Immigrant, 2007

There is so much going on in Wyclef Jean’s 2007 hit “Sweetest Girl.” Akon not only gets off the kind of beautifully melodic verse that made him the biggest star of the era but also sings a hook about the Wu-Tang Clan. Wyclef, whose own verse is about a school crush who becomes a prostitute with an ungrateful pimp, stars in the video for some reason as a secret agent who receives his briefs on a Sony Vaio phone and who is tasked with rescuing a woman slated for deportation (much respect to Wyclef for caring about this issue, however dubiously it’s presented, a decade before your neighborhood Twitter activist). And Lil Wayne is in it.

At the time, Wyclef explained the song thusly, in an interview with Prefix: “The joint the “Sweetest Girl” is about the girl that I was with in high school. She was the baddest girl in the school. But the thing about it is, this is what I’m telling the dudes: Let me give you guys a tip. The baddest chicks in high school, they become the busted chicks.” Honestly, the message gets a little convoluted. He goes on to explain:

For real, the “Sweetest Girl” can be any girl. I don’t want no girl looking at this like, “He don’t think I’m the sweetest girl because I’m fat or because I’m skinny.” It’s all within the characteristics. My verse was about the “Sweetest girl, she got on crack / she still the sweetest girl.” Akon’s verse was about the stripper; she’s not trying to ho, but she’s still the sweetest girl. Weezy’s verse is sleeping with the pastor, and she’s still the sweetest girl. Pick your choice, but don’t disrespect the women for what they do. You go to the strip bar, drop a hundred.

But the general idea seems to be reserving judgement and endorsing a sex-positive look toward sex workers, which, once again, puts the song a decade or so ahead of its time in terms of popular liberal social causes. It’s a message that doesn’t totally resonate—I think Wyclef’s verse is supposed to be about how the protagonist needs to embrace the C.R.E.A.M. mindset and get away from her pimp?—but it’s a nice idea, I suppose. Ultimately, it’s Wayne’s verse that brings things home. It’s a rare case of him taking on a narrative in a feature appearance. He builds on the themes laid out by Akon and Wyclef but expands on them in new ways with writing that contains a reveal in almost every line.

“She used to run track back in high school / now she tricks on the track right by school,” Wayne raps, seemingly about to tell a familiar story of a fall from grace. But then he scolds the listener for feeling anything other than compassion: “She takes the loss ’cause she don’t want to see her child lose / so respect her or pay her for the time used.” It doesn’t end there, though. Wayne continues to flip the moral script, explaining how this woman seems ready to turn to religion to find a way out: “And then she runs to the pastor / and he tells her there will be a new chapter.” But then it turns out that the pastor is the same as everyone else, and he was just a client: “But she feels no different after / and then she asks him: ‘where my money at?'”

I’m not sure the song ever quite delivers on its premise, but it’s a catchy song, and it deserves points as a pop experiment as well as for bringing together the range of talents that it does. And in the end, it stands as one of Wayne’s most structurally interesting verses, a moment of him effortlessly proving his chops in service of trying to do something else, quietly advancing his case in 2007 as the Best Rapper Alive.

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