Dan Humphrey of "Gossip Girl" almost had to be played by a different actor. At the start of "Gossip Girl," Penn Badgley had already starred in short-lived shows on The WB (which soon became The CW) and was hesitant to take on another high school role. In 2012, following the end of "Gossip Girl," he spoke to Vulture about why he hesitated to take on the role and noted that he was wary of being typecast — he feared there would be "no way [he'd] get out of that thing."

Badgley further explained, "I've just done so much television. I've been getting a gift from the head of Warner Bros Television since I was, like, 15 years old. That's 10 years, pushing on 11. ... I was frustrated and I was broke and I was depressed and I was like, I cannot do that again. I can't." However, his manager and his parents helped give him the push to sign on to play Dan.

Co-creator Stephanie Savage also implored him to reconsider, but he still turned the role down before finally agreeing. Badgley continued, "And then they couldn't find anybody for it — which is weird, because a million people could play Dan Humphrey — and she came back around, I was about to get a job as a waiter, and I was like, 'Okay.'"