This brown-eyed boy with a slick hairstyle would go on to become a regular actor on a TV series starring a lot of girls. Well before that, though ... this Omaha, Nebraska kid did community theater with Conor Oberst, who would go on to form the band Bright Eyes.
Need more clues? He got his start in the entertainment biz doing voice-over work and commercials, including a "Grease" spoof with Amy Adams in 1997.
His voice-over skills still land him roles to this day, but the actor really made a name for himself as the star of a 2011 Broadway musical ... for which he received a Tony nomination. Oh, and he won a Grammy for Best Musical Theater Album for his righteous role.