16. Kid Cudi

Complex says: Not only did Converse hand-pick Cudi for its Artists Series last year because of the rapper's love for Chuck Taylors, but Cudi's been known to circle through classic Jordans more than most celebrities. It's clear he prefers the IIIs and IVs, but when it's not JB, he'll even do Vans Authentics. Oh, and he also copped six pair of Air MAGs when they dropped.