#3 – Bruce Willis
Even in the days of Die Hard, Bruce Willis’ hairline was on its way out the door. He just about got away with it when he starred in the charming detective drama/sitcom/romcom Moonlighting in the 1980’s, but things eventually had to change. By the time he starred in Twelve Monkeys in 1995 he had fully embraced his baldness (until a Farrah Fawcett-style wig was required as a disguise in the latter half of the movie, anyway). He hasn’t gone back since. Bruce has moved from tough guy to comedian and back again dozens of times, but he has never looked better than he does with his bald head and twinkling green eyes. If you need further proof, check out the scenes in Looper showing his character’s transformation from Joseph Gordon-Levitt into his older self. That floppy combover will make your hair curl.