Ian Somerhalder - Young Americans - The Vampire Diaries
Somerhalder got his first series regular role in Young Americans in 2000, where he played Hamilton Fleming, a prep school boy who thought he fell for another boy (she was a girl hiding her sex to get into the school!). More series roles in Smallville (2004), Tell Me You Love Me (2007) and Lost propelled him to stardom on The Vampire Diaries.
Oooh, you know I don't know. Every time we try and go on a date you get kidnapped, I get sent to a prison world, or your feelings get compelled away...