Joshua Goldman
Joshua Goldman
min read · June 14, 2025 · Entertainment

Breaking Free: Chace Crawford's Escape from 'Pretty Boy Jail' After Gossip Girl

Zoolander once said, 'I'm pretty sure there's a lot more to life than being really, really, ridiculously good looking. And I plan on finding out what that is.' Chace seen here March 12, 2022

Chace Crawford Breaks Free from "Pretty Boy Jail"

In a recent episode of The Good Guys podcast, Chace Crawford, 39, spills the tea on his journey out of the "pretty boy jail" he felt trapped in after Gossip Girl.

The CW drama catapulted him to stardom as the dashing Nate Archibald, but success came with a price. Crawford confesses that it was a creative obstacle that stifled his growth as an actor: "I felt like I was in the wilderness for years after Gossip Girl...because people thought, 'Oh, that's not cool anymore.' And I'm in this box now."

Ed Westwick, Chace Crawford and Penn Badgley arrive at Gossip Girl premiere party on September 18, 2007 in New York City

He describes being typecast as a pretty boy and romantic lead, with Hollywood refusing to see him beyond that image. Crawford admits he was harder on himself than he needed to be: "I think people think actors make a ton more money and have way more agency than we actually do."

But Crawford's persistence paid off when he landed the role of The Deep in Amazon Prime's hit series, The Boys. This dark, gritty satire marked a turning point for him, allowing him to break free from the "pretty boy" label.

"I was probably harder on myself than I needed to be," Crawford reflects. "I wanted to dig my teeth into something more, you know? And when I read the pilot of The Boys, I was like, 'Oh, this is f**ing great.'"

Chace Crawford has been in search of what that is since he broke out of the 'pretty boy jail' he felt he was in during and after Gossip Girl. Seen here in 2009

Crawford shares that he instantly connected with the insecure and self-absorbed character: "You know, I know a hundred of those guys. So, I instantly felt confident and excited about my take on the character." He nailed the audition by reading two contrasting scenes, which won over the showrunner.

"It was great," Crawford says. "I was so happy to have another job that I was excited about, and the character was so different from anything that I had done before."

Fast forward to his love life: Crawford has been spotted with Victoria's Secret model Kelsey Merritt, 28. On Alex Cooper's Call My Daddy podcast, he reveals his dating dealbreakers: "Punctuality" and "bad tats." When asked about his stance on neck tattoos, Crawford quips, "Maybe a neck-tat is probably a deal breaker for me," but hastily adds, "It’s actually never happened!"

He played Nate Archibald in the early-2000s TV drama and said the success of the show became both a career-defining moment and a creative obstacle. Seen here in 2009

With his newfound confidence as an actor, Chace Crawford is ready to take on new challenges. Will he continue to break free from the constraints of Hollywood, or will he remain stuck in the "pretty boy" box? Only time will tell.

Sources:

  • The Good Guys podcast
  • Alex Cooper's Call My Daddy podcast

'I felt like I was in the wilderness for years after Gossip Girl,' Crawford, 39, confessed on a recent episode of the Good Guys podcast. Seen here May 18, 2025

'Because I felt, you know, as big of a show as it was, coming off of it as a young guy, it's like,

'And I'm in this box now. I'm in this jail of like the CW pretty boy, you know what I mean?' he adds, noting that people didn't think he had any 'range.' Seen here January 8, 2024

Crawford found success after Gossip Girl, but he shared that it was far from easy. Seen here May 18, 2025