Usher

Usher graduated from heartthrob to icon with a ballad-heavy blockbuster fourth album documenting his split from TLC's Rozanda "Chilli" Thomas. Occupying the middle ground between R. Kelly's bad boy and Babyface's loverman, Usher confessed to having a pregnant chick on the side but still managed to get crunk with Lil Jon and Ludacris.

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