9. LL Cool J
It's especially sad to watch LL Cool J fall off, considering he built what so many stand upon. That was him in the Kangol and adidas; that was him screaming "Don't call it a comeback/I been here for years!" in 1991. "Doin It" and "Loungin" still sound fresh today, but that was over a decade and a half ago; somehow, LL's still aiming for middle school girls' ears like a wet willy. (He also appeals to moms, though no one in between. Might have something to do with the lip-licking.) Now he's got one foot in corny and the other in irrelevant: he recorded a song based around the CBS show NCIS, and recently put out another called "Ratchet." Someone tell this old man to grow up.