Year: 2000

Yeah, Ashton Kutcher re-popularized trucker hats, Justin Timberlake tried to take credit for re-popularizing trucker hats, and we'd freak out if we saw Judah Friedlander on 30 Rock without one, but really, the first person to make them look cool in the new millennium was Pharrell in the video for "Shake Your Ass." Of course, back then hip-hop fans were stuck in their "I'm a thug thus I wear fitteds" phase, and the look didn't really take off in the rap world, but we'll never forget that P was the true pioneer.