Ashton Kutcher hoped to attend MIT or Purdue to study engineering.
But the former "Punk'd" host lost his scholarships and was kicked out of the National Honors Society after breaking into his high school as a prank. He ended up at the University of Iowa, but dropped out at 19 to pursue modeling. Kutcher now divides his time between acting and smart investing in companies like Airbnb, Spotify, and Foursquare.
"The sexiest thing in the entire world is being really smart," Kutcher said during his acceptance speech at the 2013 Teen Choice Awards.