Date: June 2009

What happened? It was only a matter of time: Taylor enlisted T-Pain for her rap debut, giving rise to a true “WTF?!” moment. She released “Thug Story”—a rap remix of her highly successful single “Love Story,” complete with a thugged-out video—at the 2009 CMT Awards. What the country music audience made of all this ain’t hard to tell.

Complex says: Taylor might have been trying to crack a joke when she rhymed, “No I ain’t got a gun/No I never really been in a club/Still live with my parents/But, I’m still a THUG!” But the truth is that most Internet rappers aren’t much different from her in those categories.