40. Sugar Ray Leonard
Cockiest Quote: "We've all been blessed with God-given talents. Mine just happens to be beating people up."
You know what's worse than getting beat by someone? Getting beat by someone who taunts you mercilessly as they're beating you. Sugar Ray would not only pummel his opponents (36-3-1, son!) but the Hall of Famer would showboat at the same time. #futurebeforefuture