Penn Badgleyis best known for his roles in Gossip Girl and Netflix's You, which makes me continuously surprised he almost played an iconic — and very different — character inBreaking Bad. Badgley broke out as Dan Humphrey in The CW's teen drama, Gossip Girl, in 2007. After that, it's no surprise that he was getting attention and auditions before Breaking Bad's debutin 2008. However, given how heavily associated with other roles Badgley has become, it's difficult to imagine his career going any other way.