Penn Badgley might be a household name these days thanks to roles in Gossip Girl and hit Netflix series You, but he's actually been acting since the late nineties.
The 34-year-old star first moved to Los Angeles at the age of 11 with his mother Lynne and bagged a pretty amazing role at the tender age of 12.
US sitcom Will & Grace landed on TV screens in September 1998, and the following year, a teenage Penn made his appearance in an episode titled 'I Never Promised You An Olive Garden'.
The episode sees one of the main characters Karen Walker drag Jack McFarland along when she attends a parent-teacher conference at her children's school.
A chance encounter with a sensitive young boy named John helps Jack face his traumatic experiences as a victim of bullying - and this is where Penn comes in.
In the short scene, 12-year-old Penn plays a bully who teases another child by insinuating that he's gay.
Penn's character and another bully are told off by Jack, who tells them: "This macho bully schoolyard crap is so 1983 I could vomit. Now scram!"
Of course, Penn looks worlds away from Dan Humphrey or Joe Goldberg in the scene - but instead is fresh faced and dressed in a scruffy school uniform.
His brief appearance in Will & Grace led to him bagging a main role the following year on TV series The Young and the Restless.
Penn also enjoyed a main role in Do Over, The Mountain and The Bedford Diaries.
However, in 2007 he landed the jackpot when he said yes to playing Dan in hit TV series Gossip Girl.
Penn has previously admitted that he turned down the role twice because he was frustrated that he had already been typecast for multiple dramas.
"I was frustrated and I was broke and I was depressed, and I was like, 'I cannot do that again. I can't'," he told Vulture in 2012.
He accepted the role in Gossip Girl just as he was about to accept a job as a waiter.
Gossip Girl came to an end in 2012, which led to Penn landing a few movie roles as well as two episodes playing Jamie in The Slap.
In 2018, the first season of You was released - and Penn had fans hooked once again as he took on the role of creepy Joe Goldberg.
Penn has previously revealed that he was also reluctant to take on this role as well as he wasn't keen on portraying a serial killer.
"I didn't want to do it — it was too much. I was conflicted with the nature of the role," he told Entertainment Weekly in 2018.
However, he said the creators thought he'd be great for the role because of how important it was for viewers to understand Joe's humanity.
"To be honest, in the beginning of the process, I had no interest in humanising [Joe]. Like, please, spare us," he added.
"But then I realised the only thing you can do as an actor is bring a character to life, and all that means."
You seasons 1 - 3 are available to watch on Netflix now.
