Album: Thank Me Later
Release Date: June 15, 2010

Drake's style was kind of…well, boring in 2010. A mix between a Banana Republic catalog and a suburban kid who shops on Karmaloop, Drake was decidedly clean-cut and still relatively untested—both sartorially and musically. His public appearances either have him in a black suit for formal occasions, or with basic dark wash denim and a hoodie or T-shirt. Looking back, it's not surprising that he was viewed more for being the dude girls could take home to their parents and less for his attempts at hip-hop greatness. But when you're marked as a Gap ad stand-in from the jump, that means you only have to create bigger and better things to overcome the stigma.