The Madd Rapper is a character played by iconic Bad Boy producer Deric “D-Dot” Angelettie. His comedic skits are perhaps the most famous hip-hop interludes of all time, appearing on three blockbuster albums in 1997: Biggie’s Life After Death, Puff Daddy’s No Way Out, and Ma$e’s Harlem World.

The character is a parody of hardcore underground rappers who are mad at Bad Boy because of their massive crossover success. In the skits, he’s a guest on a talk show where he vents about Biggie, Puffy, and Ma$e, and coins the catch-phrase “I'ma tell you why I’m mad!”

A Madd Rapper album, Tell ’Em Why You Madd, was released in 2000 on D-Dot’s Crazy Cat Catalogue label through Columbia Records. The album featured an Eminem verse and six songs produced by D-Dot’s young protegé, Kanye West. The Madd Rapper also appeared on 50 Cent’s 1999 debut single “How To Rob.”

In 1998, D-Dot was charged with assaulting Blaze Magazine editor Jesse Washington after he published a photo that revealed The Madd Rapper’s identity (which was already widely known in the music industry).