From ‘Gossip Girl’ to ‘You’! Behold Penn Badgley’s Complete Transformation Over the Years

If you were (and still are) a huge fan of Gossip Girl, then you already know that Penn Badgley — a.k.a. Daniel Humphrey — is one of the dreamiest actors of all time. Sure, he didn’t have effortless man bangs like Nathanial Archibald (Chase Crawford) or fanciful pocket squares like Chuck Bass (Ed Westwick), but there was just something special about Lonely Boy. Ahem, his bone structure certainly doesn’t hurt. 

As it happens, though, Penn’s career includes a lot more than cohabiting with Manhattan’s elite. In fact, the Maryland native’s first acting credit dates all the way back to 1999 as an extra in an episode of Will & Grace.

After that, Penn went on to land a gig on The Young and the Restless for 10 episodes. Of course, it wasn’t until 2007 that he officially became a household name. Scroll through the gallery below to see Penn Badgley’s complete transformation and career highlights.