2003 Accomplishments: Was instrumental in 50 Cent's success. The U.S. Secret Service investigated whether or not he had threatened the president.

The reigning king of the sweatsuit was rocking cozy boy steez before your favorite menswear blogger had even heard of J. Crew. He was probably the only white boy who could get away with rocking a du-rag, but he definitely inspired copycats who then got their asses handed to them.