Greg Baker – 53

Gregory Baker was best known to teens as Miley Stewart’s history teacher on Hannah Montana, Disney‘s smash hit show. Another one of his better-known projects is Sports Night, where Baker played the role of a producer named Elliot.

However, despite having gifted talents, he never had a regular stream of screen space. After a few appearances in 2012 and playing the lead role as Burger Pitt in the series I’m in the Band, it looks like Baker has taken early retirement from the showbiz, only to enjoy his days in peace and contentment.