Getty Images 1 / 50
While studying biochemical engineering at the University of Iowa and working at a General Mills factory, Ashton Kutcher won a trip to NY in a modeling contest. He secured an agency contract within three days and booked campaigns with Calvin Klein jeans and Abercrombie & Fitch, where he met fellow model/future girlfriend of three years January Jones. His shaggy hair was perfect for That '70s Show, on which he plays hunky airhead Kelso for seven seasons. His good looks, sense of humor and growing fame with the teen set helped him land People's 50 Most Beautiful People list twice and numerous films like Dude, Where's My Car?, Just Married and The Butterfly Effect. He's wears all three trucker hats (creator, host, producer) on the celebrity hidden-camera prank series, Punk'd. The show's such a huge hit that when he starts stepping out with Demi Moore, 15 years his senior, people wait for the punchline. It never comes as the duo got hitched in 2005, her daughters referred to him as "My Other Dad" and years of TMI tweets follow. He produced the matchmaking contest Beauty and The Geek for the CW and continued to bank mostly mediocre comedies (Valentine's Day, No Strings Attached). In 2011, he replaced Charlie Sheen on Two and a Half Men for a reported $650,000 an episode, but got divorced amid infidelity rumors. Things were looking up in 2012 when he started dating his '70s girlfriend Mila Kunis and is playing Steve Jobs in a biopic.