24. Terry Kennedy
Namedrop: "My style is very Tennessee, mixed with some Terry Kennedy" - Drake, "Kick, Push (Freestyle)" Room For Improvement.
Contrary to popular belief, skateboarding has always been loosely affiliated with Hip-Hop. The outsider attitude that skaters carry is a extremely similar to that of the blossoming Hip-Hop scene of the late 80s. It wasn't until the mid 2000s when Hip-Hop fully embraced skating with guys like Lupe Fiasco, Pharrell and now Lil Wayne and Hopsin really embracing the culture. The unofficial skater of Hip-Hop is Terry Kennedy, or "Compton A$$ Terry" as he was affectionately known as on the MTV show, Viva La Bam.