You Know You Love Me: Gossip Girl’s Classic Hollywood Homages, Ranked

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Photo: The CW

Even ten years later, no show does a cold open like Gossip Girl. Blair Waldorf’s love of Audrey Hepburn was as important to her Upper East Side queen persona as her headbands, and the show packed its episodes with classic Hollywood references where Blair’s dream sequences cast herself as Hepburn. It was like playing dress-up with a high-schooler who watched too much TCM, each cold opens reflecting a playfulness and extravagance that few shows lean into.

“The saddest thing that has happened is that network television has decided that it is not important to tell aspirational stories,” executive producer Joshua Safran told Vanity Fair earlier this year. Gossip Girl’s cold opens were evidence of that aspiration: It was okay if you couldn’t quite follow Blair’s Hepburn references or hadn’t sipped a martini alone at a bar yourself. This was a teenager’s idea of pseudo-adulthood, after all, packaged pretentiously with style. Below, we rank Gossip Girl’s classic Hollywood homages from worst to best.

10. “Enough About Eve” (Season 3, Episode 6)
I’d still very much like to be excluded from this narrative. This is like an uncanny valley of All About Eve references — it looks kinda like All About Eve, but something about the visual feels unrecognizable. This sequence, and the petty NYU drama that causes this stress dream, feels sophomoric. Let’s not pretend that a character as thinly sketched as Vanessa is nearly as vicious as Eve Harrington.

9. “Easy J” (Season 4, Episode 6)
By the fourth season, the cold opens began to feel more rote. Season one exhausted the Breakfast at Tiffany’s Audrey Hepburn scenes, and so “Easy J” wound up using 1967’s Wait Until Dark. Paranoid that Little J has come to take throne, this scene shows Blair as Hepburn, being attacked by a masked figure with blonde hair. In this dream, though, Little J is a far more serious foe than she ever was in real life.

8. “Shattered Bass” (Season 4, Episode 21)
Blair and Prince Louis zoom down Park Avenue on a Vespa, Roman Holiday–style. But the Vespa starts going faster and faster until Blair checks the bike’s side mirror to see exactly who she’s holding onto. The prince transforms into Chuck, and they speed away, out of control. Using “One in the World” by Tapes ’n Tapes doesn’t match the scene’s nightmarish twist.

7. “The Big Sleep No More” (Season 5, Episode 7)
This one mimics Sabrina’s tennis-court scene when Humphrey Bogart flirts with Audrey Hepburn, even though he knows she has eyes for his younger playboy brother played by William Holden. Blair is happily in love with Louis, but Chuck is making headlines on Gossip Girl and in the New York Journal with his philanthropy, trying to be her perfect gentleman. All the set pieces are there — Blair’s dress and hair look exactly like Audrey’s — but this cold open is only one-minute long. Plus, it nixes Bogart’s best line: “It’s all in the family.”

6. “The Unblairable Lightness of Being” (Season 3, Episode 18)
Chuck encroaches on Blair’s territory in this episode, getting his own a dream sequence for once. His is noir-themed — of course he dreams in black and white, he’s Chuck Bass — casting himself as the PI chasing after his kidnapped lover. If Blair is Audrey, does Chuck really have to be Bogart?

5. “The Blair Bitch Project” (Season 1, Episode 14)
“Cat? Cat!” Blair screeches, pacing around an alley à la Audrey Hepburn in Breakfast at Tiffany’s last scene. That 1961 sequence ended with Hepburn and her lover, George Peppard, in an embrace. Blair’s dream sequence, meanwhile, turns into a nightmare: Nate is dressed as Peppard, but harshly confirms Blair’s greatest fear. He calls her Jenny and tells her that not only does she not have a cat, she doesn’t have anyone anymore. The rain makes this scene a hard one to pull off, but the scene itself isn’t as iconic as some of the others Gossip Girl executed.

4. “Seder Anything” (Season 2, Episode 21)
The second season’s focus on college applications delivered not one but two My Fair Lady cold opens. This one, which features a Blair versus Blair smirkfest, should’ve been more successful. In it, Queen B plays both Eliza Doolittles: the flower girl with the Cockney accent and the refined lady in the white hat. Leighton Meester has trouble selling the high-society inflection, and Chace Crawford doesn’t have anything to do but sit beside her and wear those man bangs.

3. “New Haven Can Wait” (Season 2, Episode 6)
It’s Blair against Serena in the better of season two’s My Fair Lady cold opens. This is how it feels to be 17 years old, stressed, and self-pitying: Blair’s nightmare casts her as Eliza Doolittle dropping her r’s and reciting phonetic exercises while Serena glides into the room and breezes through everything that’s giving Blair trouble. At this stage in college admissions, every Ivy — including Blair’s beloved Yale — wants the “Page Six” darling Serena to up their cool factor. There were more fun ways of getting at Blair’s Queen S insecurity, but this cold open belongs high on the list because it was one of the more inventive ways the show capitalized on Blake Lively’s cleavage.

2. “G.G.” (Season 5, Episode 13)
I adamantly believe that Blair was Gossip Girl’s true main character, but even I have to admit that Serena’s only cold-open fantasy sequence was pretty damn ridiculous. Gossip Girl was past its prime when it hit its 100th episode, but we were entering the era of peak Blake Lively. Casting Serena as Marilyn Monroe was more obvious than a brilliant bit of stunt casting. Even though it wasn’t as sly as the Blair-focused cold opens, it felt like the last hurrah: Let’s make everything big and pink and ostentatious and tacky! Plus, it had the Upper East Side’s two queens fighting over a lowly Brooklyn boy a couple years away from a man bun. Why not have a little fun with the show’s descent into total melodrama?

1. “Bad News Blair” (Season 1, Episode 4)
Gossip Girl’s first cold open got to the heart of the show’s primary insecurity: As much as Blair loved Serena, Queen B was terrified that she would usurp her power in public and private. Serena was the five-foot-ten wild child brimming with personality. Everyone gravitated toward Serena — even Blair’s own mom. This dream sequence is appropriately extravagant: Blair is dressed as Audrey Hepburn, mimicking the Breakfast at Tiffany’s opening scene. Instead of ogling diamonds, though, she’s thrown off by a window display showing Serena in Blair’s dress from the pilot, with two Constance Billard underlings by her side. Then Gossip Girl twists the knife. Serena’s hair is in loose ringlets, and atop her head is Blair’s crown: a headband.

Gossip Girl’s Classic Hollywood Homages, Ranked