25. George Clooney
Why He Made The Cut: The classic gentleman playboy.
Thanks to E.R., Clooney got his head in the game. Literally. His Caesar-inspired haircut became the de facto style for dudes much in the same way '90s ladies flocked towards "The Rachel." Besides his influence on '90s grooming, he also knew how to look great in a suit, something he continues to do today.