When Ashton Kutcher won a Fresh Faces of Iowa modeling contest in 1997, he left for New York where he appeared in ads for Calvin Klein. Shortly afterwards, Ashton landed the role of the dim-witted hunk Michael Kelso in That ‘70s Show. Spending years in front of the camera, Ashton went on to create, produce, and host MTV’s Punk’d. Ashton also went on to conquer the film industry, starring in Just Married, The Butterfly Effect, and Valentine’s Day. When it comes to Ashton’s love life, he had jaws dropping when he began dating actress Demi Moore, 15 years his senior. The two wed in 2005 in a ceremony attended by close friends, family and Bruce Willis, Demi’s ex-husband. In 2011, Ashton will return to TV, replacing Charlie Sheen in the comedy series Two and a Half Men.