THE RUNDOWN
- The Pretty Reckless released a video for the band’s new single, “When I Wake Up.”
- In the video, Taylor Momsen shares screen time with her former Gossip Girl co-stars, Jessica Szohr and Connor Paolo.
- Momsen previously referenced her Gossip Girl character, Jenny Humphrey, on the cover of The Pretty Reckless’s forthcoming album, Dear God.
Taylor Momsen might have ended her time on Gossip Girl prematurely, but she still has love for her Gossip Girl co-stars—and even featured two of them in The Pretty Reckless’s latest music video, “When I Wake Up.”
The video largely takes place from Momsen’s point of view as she embarks on a wild night out. After having a cup of black coffee spiked with liquor, she heads to a bar to meet up with her friends. Jessica Szohr, who starred as Vanessa Abrams in Gossip Girl, is seen playing a heated game of foosball alongside Connor Paolo, who played Serena van der Woodsen’s younger brother, Eric, in the show.
Momsen has a true reunion with Szohr and Paolo in the bar’s photo booth and takes multiple pictures with each of them. After Momsen leaves the bar, she finds herself in bed next to Paolo as he hooks up with a girl. (Paolo’s Gossip Girl counterpart was gay in the show.)
Szohr and Paolo’s cameos in “When I Wake Up” come after Momsen subtly referenced her own Gossip Girl character, Jenny Humphrey, on the cover of The Pretty Reckless’s forthcoming album, Dear God. In the album cover, the singer wears a blue plaid pinafore dress similar to the uniform that Humphrey would wear in the show while attending Constance Billard School for Girls.
Momsen notably left Gossip Girl as a series regular after the third season of the show to focus on her music career. During her November 2025 appearance on the Call Her Daddy podcast, the singer revealed that she didn’t tell her fellow castmates about her exiting the series. “I kind of just Irish-dipped. I just wasn’t on the script the next week,” she said.
“They all knew I was making music. They all knew I had a band. I would play them stuff because I was working on the first record while I was on the show,” Momsen added. “I would come in and play songs…but I don’t think anyone knew how serious I was at that stage.”
Leaving the contract was a difficult task, with Warner Bros. Television even calling her “ungrateful” for wanting to quit the show.
“I just went, ‘Fuck you. You don’t know what you’re talking about. You’re not in my shoes, so how dare you judge this?’” she recalled. “I was very defensive, but it came down to they wouldn’t let me out of the contract. The head of Warner Bros. said, ‘Fuck Taylor Momsen. No fucking way.’” Momsen was later written out of Gossip Girl by its creators, Stephanie Savage and Josh Schwartz, but did make a cameo in the 2012 series finale episode.
“As a fan of television and a fan of the shows, I love when you have the full cast together again,” Momsen said of her 2012 Gossip Girl return. “You want to full-circle that and round it out.”
‘ The preceding article may include information circulated by third parties ’
‘ Some details of this article were extracted from the following source www.elle.com ’
