From: The Notorious B.I.G "Kick In The Door" (1997), Ma$e "Madd Rapper Skit" (1997), Puff Daddy "Madd Rapper Interlude" (1999), 50 Cent "How To Rob" (1999)

Who they were: After making his debut on a skit on Biggie's album, the Mad Rapper—who was voiced by Hitmen producer Deric "D-Dot" Angelettie—also appeared on skits for Black Rob, Mase, The LOX, and 50 Cent. And the Mad Rapper eventually got so popular that he released his own album in 2000 called Tell 'Em Why U Madd that featured him rapping alongside Raekwon, Busta Rhymes, and Eminem. Looking back at it now, it was quite the come—up for a fictional character.

Where are they now? After undergoing more than a decade of therapy, the Mad Rapper has finally learned how to control his anger and is no longer mad... Sike! He's actually still mad as hell and is reportedly putting together a new album called, what else? Still Mad.