What is Pretty Boy Jail? Chace Crawford Speaks Out—Meet the Other Stars Who’ve Served Time
“Pretty Boy Jail” might sound like an inside joke from a long-lost Tumblr era or a catchy line from a CW drama binge. Yet, according to Gossip Girl alum Chace Crawford, this phenomenon is all too real.
Chace Crawford’s Tale from the Good Guys Podcast
In a recent episode of the Good Guys podcast, Crawford candidly shared his journey post-Gossip Girl, where he was celebrated as the quintessential CW heartthrob. “I felt like I was in the wilderness for years after Gossip Girl,” he reflected. “As popular as the show was, transitioning from it as a young guy felt limiting. It’s like, ‘That’s not cool anymore,’ and I was trapped in this box—a jail of the CW pretty boy with no range.”
This effectively encapsulates the concept of Pretty Boy Jail: gaining fame for your looks, only to be punished for it when the roles start to dry up. Although no one explicitly tells these men they’re being typecast, the resulting career stagnation speaks volumes. You might just become that guy who peaked during a moody hallway scene in Season 2.
The Long Path to Redemption
For Crawford, it took almost seven years before he finally landed a role that allowed him to showcase his versatility. Enter The Deep in The Boys—a character that transformed not only his career but also his self-perception. “When I got that audition,” he recalled, “I thought, ‘That sounds wild!’ After reading the pilot, I was like, ‘Oh, this is great. It’s so original and weird.’”
He resonated with the role instantly, saying, “I’m like, ‘I know that guy. I know a hundred of those guys.’” It’s this level of unexpectedness that can shatter the confines of Pretty Boy Jail, much like what happened with his Gossip Girl co-star Penn Badgley. “I was really, really appreciative when this happened,” he added.
So, is Pretty Boy Jail a real phenomenon? Absolutely! But Crawford isn’t the only star who’s served time behind its metaphorical bars.
Other Inmates of Pretty Boy Jail
Chad Michael Murray
The Blueprint: From One Tree Hill to A Cinderella Story and House of Wax, Chad Michael Murray’s face was everywhere in the 2000s. However, once his leading man roles dwindled, Hollywood’s interest in him faded too. He pivoted to Hallmark movies and Christian thrillers, but the mainstream never provided him with a second act.
Jesse Metcalfe
The Hot Gardener: Known for his role as the eye-catching gardener on Desperate Housewives and the star of John Tucker Must Die, Metcalfe was always cast as the “dream guy”. Like Crawford, he has continued to work, appearing in films like the 2023 release Fortress, but we can’t help but yearn to see him land a significant role again.
Matt Lanter
CW Royalty: After gaining fame from 90210, Matt Lanter found himself stuck in the Pretty Boy Jail loop. Interestingly, some of his best work has come from voice acting, notably in Star Wars: The Clone Wars. While he has the looks, casting directors often seem more comfortable wielding his voice than highlighting his striking face.
Taylor Kitsch
From Beloved to Banned: Thanks to Friday Night Lights, Kitsch built a strong fanbase but found his career nearly derailed by John Carter. Too handsome for gritty roles and too stoic for comedic ones, it wasn’t until projects like Waco and Painkiller that audiences were reminded of his acting chops. Currently, he’s starring in American Primeval, a Netflix Western miniseries scheduled for release in 2025—so we can say he’s been freed for now!
Ed Westwick
Chuck Bass Forever: After Gossip Girl, Ed Westwick’s career took a nosedive. Despite facing legal challenges (allegations that were later dropped), he found himself pigeonholed into “rich bad boy” roles, leaving Hollywood at a loss regarding his next steps.
Steven Strait
Teen Dream turned Expanse Star: Remember him from The Covenant? For a time, he was the reigning heartthrob across countless Tumblr dashboards. Though he has continued to work—The Expanse provided him with a steady gig until 2022—he never quite reached the leading man status many predicted.
Alex Pettyfer
Once hailed as Hollywood’s next big thing, Alex Pettyfer starred in Beastly and I Am Number Four. With the looks and the abs, he seemed destined for stardom. However, rumors of being “difficult” behind the scenes halted his rise (fair or not). Even his role in Magic Mike wasn’t enough to fully break him out of the confines of Pretty Boy Jail.
The tale of Pretty Boy Jail is a potent reminder of how Hollywood can be both a launching pad and a trap for young talent. As we track the journeys of these once-beloved stars, we can’t help but wonder: Who will break free next?
