Taylor Swift Once Rapped With T-Pain and She Was Never the Same

Let's see if you haven't purged "Thug Story" from your mind yet.

Reputation finds Taylor Swift making her strongest bond with hip-hop to date, despite a year that's seen some associating her with white supremacy. The rap connection is most apparent on "End Game," which features herself, Future, and the Ginger J. Cole, Ed Sheeran, spitting on My Beautiful Dark Twisted Fantasy-ish production. This is not too surprising, not only because rap is huge now but also because Swift is a legitimate fan of the genre. She flirted with Lorde-filtered pop-rap sounds on 1989 and also collaborated with Kendrick Lamar after expressing appreciation for his work. But there is an even earlier dalliance Taylor had with this world, and it naturally involves T-Pain because everything was T-Pain in the late 00s.


"Thug Story," which aired during the 2009 CMT Awards, is obviously a parody of Swift's then-enormous "Love Story," except it's about how Taylor Swift is clearly not supposed to be rapping because she is wholesome and not very "street," i.e. extremely white ("I knit sweaters, yo!"). Perhaps you may have already seen this video, but it still deserves resuscitation because wow this is awkward, even though the song kind of goes. Taylor leans into her long-abandoned country singer drawl during lines about not going to the club and living with her parents. T-Pain sings a version of the "Love Story" chorus while Taylor yells "WHAT?!" in his ear like a very self-conscious N.O.R.E. It was a different, wilder time. Despite her enthusiasm for rapping here, Swift's immediate next album was the epic-length, Rococo masterpiece Speak Now, which featured no hip-hop elements but did have Swift writing the most detailed and damning lyrics of her entire career. Rap would only enter later, though the seeds of that love may have been sown here.

What's definitely true is this: "Thug Story" is a very weird cultural artifact that looks even stranger given current context. You could definitely never run something like it on TV now because we're much more critical of using stereotypes as a cheap laugh. We already saw this go down for Swift when she donned a similar "gangsta" get-up in her "Shake It Off" video and drew the ire of writers who felt it was appropriative of black culture. She even made a similar mistake with "Look What You Made Me Do" and its Lemonade-reminiscent visuals. Maybe "Thug Story" more accurately represents the beginning of a descent into bad judgement calls for Taylor. Perhaps if we don't understand our past, we'll never fix our present. At least T-Pain is still thriving, however, making great new music and being properly appraised for his past classics. The good guys do win sometimes.

Phil is on Twitter.