18. Willie Dynamite (1974)
Director: Gilbert Moses
Stars: Roscoe Orman, Diana Sands, Thalmus Rasulala
First off: Yes, that is Gordon from Sesame Street playing the pimptagonist. Second of all: Yes, the pimptagonist learns some heavy lessons, thanks in no small part to his astonishing wardrobe and a script that's often overlooked. How this didn't win an Oscar for Best Candy-Cane-Themed Fur Coat, we'll never know.