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Ashton Kutcher

Current age: 37

Career at 20: Ashton actually started out as a model. He was scouted at University of Iowa, where he placed first in a Fresh Faces of Iowa competition. He won a trip to the International Modeling and Talent Association competition and ultimately lost to Josh Duhamel. Shortly thereafter, he was cast in That '70s Show.

Relationship status at 20: Ashton was dating future Mad Men star January Jones.

Quoted at 20: When asked about his humble beginnings, Ashton confessed, "When I was first starting out, my whole goal was to not get fired. I really couldn't have imagined the success I've been given. I definitely wasn't reading that book The Secret, if you know what I mean."

Image Source: Getty / S. Granitz