What Is Pretty Boy Jail? Chace Crawford Says It’s Real—Here Are The Other Men Who Experienced It

“Pretty Boy Jail” sounds fake; it sounds more like a Tumblr meme from 2013 or something you’d say after watching too many CW dramas in a row. But according to Gossip Girl alum Chase Crawford, it’s real. 

During an appearance on the Good Guys podcast, Crawford opened up about the aftermath of his Gossip Girl fame and how being cast as the CW’s resident dreamboat became a career dead end. “I felt like I was in the wilderness for years after Gossip Girl,” he said. “As big of a show as it was, coming off [it] as a still young guy, it’s like, ‘That’s not cool anymore,’ and I’m in this box. I’m in this jail of the CW pretty boy who has no range.”

That pretty much sums up what Pretty Boy Jail is. You get famous for being hot, and then you’re punished for it. Not overtly, of course – no one tells you you’re blacklisted – but the roles disappear. You’re not seen as serious, Hollywood casting directors would probably assume you have no range. You’re typecast as the guy who peaked in a moody hallway scene from Season 2.

For Crawford, it took nearly seven years before he landed something that let him do more. The role of The Deep in The Boys changed everything. “I just remember that audition hitting my inbox and reading the synopsis, I was like, ‘That sounds wild!’ And then reading the pilot, I was like, ‘Oh, this is great. This is so out-there and original and weird.’”

He understood the role instantly. “I’m like, ‘I know that guy. I know a hundred of those guys.’ I instantly felt confident and excited about my take on the character.”

Perhaps that’s what it takes to break out – something totally unexpected, totally unhinged. Just take a look at his pretty boy co-star Penn Badgley. 

“I was really, really appreciative when this happened,” Crawford added.

So is Pretty Boy Jail real? Yeah. And Crawford wasn’t the only one doing time.

Other Inmates of Pretty Boy Jail

Chad Michael Murray

The blueprint. From One Tree Hill to A Cinderella Story to House of Wax, Murray’s face was everywhere in the 2000s. But once his leading man roles faded, so did Hollywood’s interest. He pivoted to Hallmark movies and Christian thrillers, but the mainstream never gave him a second act.

Jesse Metcalfe

He played the hot gardener on Desperate Housewives and then John Tucker Must Die. He was always cast as the guy women wanted. Like Crawford, he kept working (even appearing in the 2021 film Fortress), but we’d love to see him land something big again.

Matt Lanter

90210 made him CW royalty, but he couldn’t break out of it. Ironically, his most respected work came from voice acting (Star Wars: The Clone Wars). He had the looks, but casting directors seemed more comfortable using his voice than his face.

Taylor Kitsch

Friday Night Lights made him beloved. John Carter nearly tanked his career. He was too handsome to be gritty, too stoic to be quirky. It wasn’t until Waco and Painkiller that people started to remember he could actually act. Now he’s starring in American Primeval, a Netflix Western miniseries released in 2025, so he's been discharged for now.

Ed Westwick

Chuck Bass himself. After Gossip Girl, Westwick’s momentum stalled. He faced legal issues (the allegations were later dropped), but even before that, he was locked into “rich bad boy” mode. Hollywood couldn’t figure out what else to do with him.

Steven Strait

Remember him from The Covenant? He was the guy on every teen Tumblr dashboard for a hot minute. He’s still working — The Expanse gave him a steady run until 2022 — but he never became the leading man many assumed he would be.

Alex Pettyfer

The Beastly and I Am Number Four star was once considered the next big thing. He had the face, the abs, the teen movie pipeline. For a minute, Hollywood bet big on him. But behind-the-scenes rumors of being “difficult” (whether fair or not) stalled his momentum. Even his role in Magic Mike wasn’t enough to break him out.