Clearly trends towards more recent, especially with the Sugarhill Gang being one of the 2 or 3 least correctly guessed answers, as well as Flav being guessed correctly so little of the time. He was as iconic (if weird) in the late 1980s and early 1990s as anybody else in the game. That being said, I only got 11 out of 20 because my knowledge is mostly limited to Old School (1990s and 1980s).