3. Kid Cudi
Cudi's got it made, by most standards. From Complex covers to his music career and his recurring role on HBO's How To Make It In America, it'd be fair to envy the man a bit. But see, that just isn't enough for Cudi, so he linked up with French label Surface 2 Air to release a series of leather jackets and a short film. The only people that can pull the jackets off are Cudi himself and a space goth Michael Jackson, though, so fall back and admire from a distance.