Age: 27
Albums: Asleep in the Bread Aisle (2009).

When Asher Roth debuted in 2008 with the DJ Drama-backed The Greenhouse Effect Vol. 1 mixtape, he was pegged by many as the next white rap phenomenon, and the Top 40 success of the single "I Love College" had visions of Slim Shady dancing in label executives' heads. But the album Asleep In The Bread Aisle flopped, while other white rappers like Mac Miller and Macklemore soon swooped in to do the kind of numbers people had expected Asher to do. Now, Asher Roth is pretty much back at the spot he was at five years ago, releasing The Greenhouse Effect Vol. 2 with DJ Drama and trying in vain to get that buzz started all over again.