4. Young M.C.
"Bust a Move" (1989, Number Seven) and "Principal's Office" (1989, Number 33)
His greatest hit is (deservedly) a wedding DJ staple and (undeservedly) a punchline for snarky people who like stuff like "Stuff White People Like." But in his day, when everyone knew rap would cross over but nobody knew exactly how, this hitmaker and Tone-Loc ghostwriter seemed a contender for stardom – more radio-ready than Kid 'N Play, less kid-friendly than the Fresh Prince, lyrically nimbler than Hammer. Label hassles sidelined him for more than a year and, in the interim, the game did what the game does: changed.