Charlie Sheen & Martin Sheen

Unlike most others in this list, Charlie Sheen is not “attempting” to follow in his parents’ footsteps. He already has! Well, their family has a history of members who ended up in the entertainment industry. Like his father, Martin Sheen, Charlie became an actor.

Charlie’s acting career started when he was only a child. Now at the age of 54, it’s safe to say that he’s established himself rather well. It’s slightly ironic that some of Charlie’s best characters were in the same name. For instance, he played Charlie Harper on Two and a Half Men and Dr. Charlie Goodson on Anger Management.