14. Tim Dog
From: Bronx, NY
Signature Song: Tim Dog "Fuck Compton" (1991)
Before Dateline exposed him for running an online dating scam (SMFH), Tim Dog was one of the most hardcore rappers ever. His debut album, Penicillin on Wax, was basically one big fuck you to the entire West Coast. Tim might not have been the cleverest rapper, but he was certainly one of the most brash and uncouth. And while his sales might have been lackluster, he made enough of an impact to elicit responses from Dr. Dre, DJ Quik, Compton's Most Wanted, and more.