My list in no particular order.
1.Eddie Rickenbacker - Race Car Driver, Fighter Ace, founded his own car company, founded an Airline, survived horrible plane crash, survived being lost at sea for 24 days, spied on the Russians, called the New Deal socialism, and there was that Medal of Honor thing, what's not to like.
2.Howard Hughes- Built the first radio transmitter in Houston, had the first motorcycle in Houston, $$$$$$$$$$$$$$$$$, made cool movies, was Eve Gardner's lover, told the government to go screw itself, made the "Out Law" with Jane Russell, $$$$$$$$$, set up foundations that still have $$$$$$$$$. Yea he went a little craze at the end of his life, but man what a life.
5. Edward Weston - The best photographer of the 20th century, and quite the ladies man. Sure Adams was a better business man and technician but Weston had vision that Ansel never came close to. No photo of him just this.
6. Marlon Brando - If for no other reason than Harley-Davidson owes everything it is today to this man and the Wild One (even though he rode Triumph in the movie)
7. Hugh Hefner - More to him than just the center fold. Lots of writers got their first shot in Playboy. His influence on the American Male in the last have of the 20th Century for better or worse is hard to get around.
8. Frank and Dean. These guys defined style, grace and cool. Don't believe me? Read "The Way You Wear Your Hat."
9. Clint Eastwood - Working guy makes good in TV, then the Movies, then he starts directing movies. Still seems to be a working class kind of guy.
10. Neil Armstrong - First Man on the Moon but do you see him on "Dancing with the Stars"? Hell no, this is a man who understands the privilege that was given to him and honors that with style and grace that is beyond comprehension in today's YouTube world..