Disney turned an animated steamboat-driving mouse into an industry that completely legitimized cartoons and gave him a massive fortune. In 1955, he used some of his massive bank balance and his beloved characters to design and build Disneyland, which he later paired with a sister park in Orlando to help cement the theme park's place in American life.
Hefner built a media empire by embracing one simple truism: men will want to look at pictures of attractive naked ladies. After making a splash with Marilyn Monroe as his first centerfold, Hefner made it clear that the magazine wasn't only about naked ladies. The magazine's in-depth interviews with A-listers and fiction offerings from top writers from Nabokov to a serialization of Ray Bradbury's Fahrenheit 451 made it plausible to say you "only read it for the articles." Hefner's reward? Millions of dollars and a grotto stocked with gorgeous women. (Grotto ownership is a sure sign of genius.)
Here's a classic battle of innocence versus experience. What's more inspired: Disney's adorable, funny animations or Hefner's canny commercialization of men's sex drives? Donald Duck's unapologetic lack of pants or Hefner's delightfully affected satin smoking jackets? Remember, no one's watching you cast your vote.
[See the whole bracket here.]