9. Dolemite (1973)
Director: D'Urville Martin
Stars: Rudy Ray Moore, D'Urville Martin, Jerry Jones, Lady Reed
What started as Rudy Ray's alter ego become one of the most well-known characters in movie history. After a 20-year prison bid, the pimp/hustler sets out to find the ones that set him up. But not before getting his, uh, affairs (read: stable) in order. Pimpin' was never easy, word to Scoob and Scrap.