Howard Hughes

Position: Chairman of Hughes Aircraft, film producer, and director
Year: 1936
Complex says: Howard Hughes was the original bored rich dude. He made a fortune as a movie producer, hustling behind the scenes for old-school classics like Hell's Angels and Scarface (the original one from the 1930s).

But then he switched his game and became known as one of the most influential aviators of all time. Hughes set many records during his time. Yet perhaps his most impressive achievement occurred in 1936, when he flew from California to New Jersey in nine hours. Today, 80 years later, it takes about five hours to cover that distance. If that doesn't impress you, we give up.