Dennis Tito

Position: Founder of Wilshire Associates
Year: 2001
Complex says: To be fair, Tito has a Bachelors degree from New York University in Astronautics and Aeronautics. So it's not like dude was a complete dumb-dumb when he bought his way into space.

Still, his journey was met with some resistance. Snooty ass NASA, for example, denounced the voyage. However, nothing could take away from his legacy as the first space tourist—the only time where the word "tourist" sounds cool.