Baltimore-born actor Penn Badgley first started landing a string of roles in his mid-teens, finding his first major part with the short-lived fantasy comedy series Do Over, on the WB. Then-16-year-old Badgley starred on that program as Joel Larsen, a 34-year-old loser salesman propelled back into his high-school body to relive his teenage years and alter the course of his adult life. Following the cancelation of that show, the WB provided Badgley with his next two major roles, though both turned out to be equally shortlived; he played Sam Tunney on the soapy drama The Mountain (2004) and Owen Gregory on the ensemble collegiate series drama The Bedford Diaries (2006). Shortly thereafter, Badgley could be seen in the high-school teen comedy John Tucker Must Die.
It was in 2007 that the young actor finally found his first small-screen hit, when he was cast in a lead role on Gossip Girl, a teen drama on the fledgling CW network (itself a successor to the WB and UPN). The actor played Dan Humphrey, a Brooklyn-dwelling aspiring writer who goes to an elite private high school where his classmates are mostly Upper East Side snobs; the show became a big hit for the network, and gave Badgley his first taste of true stardom. In 2009, he took on a starring role in the remake of the classic '80s horror film The Stepfather. He went on to be in the high school sex comedy Easy A, and played one of the young corporate bankers forced to deal with the beginning of the financial collapse in Margin Call.