James Franco – 43

James Franco has wowed us with his charm and acting for some time now. If you’ve seen films like “Pineapple Express,” “James Dean,” and the 2020-released “Kill the Czar,” then you know all about his brilliance. But, while it’s the norm for actors to marry colleagues and, in some cases, non-actors, Franco is quite the exception.

Although we had hoped for a wedding when he dated “Whatever It Takes” co-star Marla Sokoloff and actress Ahna O’Reilly, those relationships eventually ended. Later, during an interview with “Playboy,” he revealed that his interest in education affected his time with O’Reilly. So it may be a while before Franco says, “I do.”