40. Mark Cuban
Maybe you’ve seen him on Shark Tank as the technology mogul who sold his software to Yahoo for $5.7 billion. Or as the outspoken owner of the Dallas Mavericks. Either way, Cuban is one of the most intelligent American businessmen today, with a knack for wise investments, and a big personality to match. He plays by his own rules and makes billions of dollars doing it. He's like Donald Trump, but with better hair and less shameless self-promotion.
39. Hunter S. Thompson
Though we’d never like to advocate drugs, alcohol, violence, or insanity, well, they worked for this guy. The inventor of “gonzo” journalism, Hunter S. Thompson took on the Kentucky Derby, presidential campaigns, and a violent motorcycle gang; he made himself a part of the action and in the process exposed the seedy underbelly on which our country’s culture is built. Sure, he may have drunk a little and dabbled in illicit substances, but he was always real about who he was, which is pretty damn American.
38. Harvey Milk
Though today one’s sexual preference is about as relevant to their public persona as what they order at Chipotle (possibly less, if you REALLY judge people for eating tofu), in the 1970s being openly gay was more or less a political deal-breaker. Until Harvey Milk came along, and won a seat on the San Francisco Board of Supervisors, contributing to landmark gay rights legislation and making San Fran an early pioneer in the LGBT fight for equality. And while he was assassinated less than a year after taking office, his mark on the community and the movement has yet to be equaled.