Billy Crudup – 52, Actor

Billy Crudup was on the verge of becoming a celebrity at the turn of the century. He had a string of potentially star-making roles just as he was starting to make his way into our minds as the face of Mastercard. The New York native took his place in a prestige drama with the father-son fable Big Fish and was very literally a rock star in Almost Famous. When it comes to the actor’s awards and investments, he won the Tony Award for his performance in The Coast of Utopia and gained several accolades under his belt since.

Looking back, Crudup ended his relationship with longtime girlfriend Mary-Louise Parker while she was seven months pregnant. He met Danes on the set of Stage Beauty, and the two began dating in 2003. However, the relationship ended in 2006, with no official announcements made during the breakup. Crudup is single as of now.