A Look Back At The Awkward Moment When Taylor Swift Proved She'd Never Make It As A Rapper

Taylor Swift is undeniably one of the biggest pop stars in the world. Her 2024 album "The Tortured Poets Department" topped the Billboard 200 chart and went platinum six times over. But, while Swift stands firmly atop the mountain of pop, an awkward moment from her past proves that she probably isn't going to be taking over the rap game anytime soon. During the earlier, more country-heavy days of her career, the "You Belong With Me" hitmaker sometimes performed live covers of rapper Eminem's hit song "Lose Yourself."

The rapper originally recorded the song for his 2002 movie "8 Mile," and released it as a single shortly before the film premiered. But while Eminem's "Lose Yourself" became one of the defining tracks of his career, Taylor's version is, well, it's no "Shake It Off," let's just say that. When one of her live renditions resurfaced on Reddit in late 2024, commenters were quick to plug their ears. "There are just some 'crossovers' we never needed to hear. This is one of them!" wrote one unimpressed user. Another her performance as "embarrassing at best," while a third proclaimed that it "could have killed Eminem's career by proxy."

But while rap fans don't seem to care much for the singer-songwriter's take, Eminem himself doesn't have any beef with her. In fact, while the rapper has famously feuded with the likes of Mariah Carey (who penned a diss track about Eminem) and MGK, he gave major props to Swift in a 2016 interview with Zane Lowe. However, Eminem added that a true friendship between himself and the "22" hitmaker was probably highly unlikely.

Surprisingly, Taylor Swift performing live covers of Eminem's "Lose Yourself" wasn't the only way she dipped her toe into the world of hip-hop during her early career. In 2009, the singer-songwriter actually collaborated with rapper T-Pain to record "Thug Story," a parody of her hit song "Love Story." However, "Thug Story" has never actually been released in an audio-only format; it's only seen the light of day in music video form. That clip was broadcast as part of the 2009 CMT Music Awards (where Swift's "Love Story" won both Video of the Year and Female Video of the Year). The "Thug Story" music video (which is available to watch on YouTube if you're curious) was also released on the bonus DVD that shipped with the "Platinum Edition" reissue of Swift's second studio album, "Fearless."

The "Blank Space" hitmaker subsequently collaborated with rapper B.o.B, appearing as a guest artist on his 2012 song "Both of Us." Swift sang, played guitar, and even appeared in the "Both of Us" music video, though she thankfully left all the rapping to B.o.B on that track. More recently, the Grammy winner collaborated with rapper Post Malone on her 2024 song "Fortnight," which was released as part of "The Tortured Poets Department." That said, neither of them really rap on that track, as it has more of a new wave sound, and Post Malone has gradually evolved from solely being a hip-hop artist in recent years. In fact, he's even dabbled in the world of country music, which is where Swift got her start.