All The Classic Film References In “Gossip Girl” You Missed The First Time Around

I just finished watching Gossip Girl for the first time, and I’m going to make the same confession Travis Kelce did recently – I totally loved it. Like everyone else who caught the famed CW show while it was on air, I loved the fashion, Blair and Serena’s tumultuous friendship, and even that ultimate will-they-or-won’t-they relationship between Blair and Chuck. But the thing that I loved most about Gossip Girl was the way the show consistently included clever homages to the classics of film history.

It’s more than just a fun Easter egg, though. Whether we know it or not, movies like Breakfast at Tiffany’s or The Big Sleep are embedded in our cultural consciousness. If there’s something timeless about Gossip Girl (something the show’s remake sorely lacks), maybe it’s because Gossip Girl is in constant dialogue with the greatest 20th-century American stories in a way that’s both reverential and tongue-in-cheek. Here are just a few of my favorite nods to classic American movies and novels in the original Gossip Girl.

So Much Breakfast at Tiffany’s

Listen up, East Siders. If there’s one thing Blair Waldorf loves more than Chuck, herself, or a good takedown, it’s Audrey Hepburn in Breakfast at Tiffany’s. Blair references the film often throughout the series directly, but it’s also the first classic movie reference that the show recreates. Stepping out of her taxi, Blair holds a pastry and a small coffee. But instead of envying diamonds through the Tiffany window, Blair sees her once best friend Serena stealing her sidekicks and her signature headband.

Blair resurfaces as Breakfast at Tiffany’s heroine Holly Golightly again later in the series, when she recreates the last scene with her on-and-off ex-boyfriend Nate. Running into an alley, Blair starts searching for Cat (the pet in the original classic film, which she has refused to take ownership of). A dashing Nate follows her in the rain…but Blair’s ending is not quite as romantic as the one Holly Golightly gets.

Chuck the Private Eye

Chuck gets a dream of his own – and like the tormented anti-hero he sometimes is, he has stepped into the shoes of a film noir detective straight out of the ‘40s. In this episode, Chuck dreams Blair has been taken away – his conscience’s way of telling him that he’s finally gone too far. This scene is a shoutout to Humphrey Bogart’s The Big Sleep and Orson Welles’ The Third Man and any other private detective who’s made a deal with the devil – and there’s a price to pay.

Serena, the Bombshell Blonde

This one may very well be my favorite. Sick with unexpected heartache, Serena gets a dream of her own, and in it, she’s the most iconic blonde in history – Marilyn Monroe herself. Whatever genius decided to give us Blake Lively as Marilyn Monroe singing the classic “Diamonds Are a Girl’s Best Friend” needs to be making all the movies, in my humble opinion. The scene is recreated with extraordinary detail, from Lively’s pink dress to the dancing dudes. But Serena wants one of the boys more than the others – and it turns out that if diamonds are a girl’s best friend, than maybe your best friend may take the boy you like.

My Fair Lady Meets The Age of Innocence

In yet another dream, Blair envisions herself as Eliza Doolittle, the eponymous “Fair Lady” who begins life as a poor flower girl and doesn’t know how to speak well. But this Eliza Doolittle gets shown up by Serena in fine garb and superb accent. In a later episode, Blair returns as Eliza Doolittle, and she offers to sell flowers to Nate and the woman he’s seated next to. But the woman turns out to be Blair herself, dressed in a white high-collar, telling herself to give up on the dream of a future at Yale.

This may be one of the cleverest references, since it covers two in one. Starting with the well-known show tunes of My Fair Lady, we end up with a scene drawn much more from Edith Wharton’s The Age of Innocence. Age of Innocence tells of a wealthy New York lawyer who is betrothed to a New York heiress but is shaken when he falls madly in love with her scandalous cousin. Ringing a bell? Maybe it’s just me, but that sounds a whole lot like the Blair/Nate/Serena triangle we first saw in season 1.

Dan Humphrey or Jay Gatsby? 

Dan Humphrey may walk around talking about Allen Ginsberg all the time (which is a classic reference all its own), but we think there’s another classic story inspiring the character of Lonely Boy: Jay Gatsby. In The Great Gatsby, we meet the romantic hero Jay Gatsby, who spends his life throwing parties and staring across the water at the home of his first love, the coy Daisy. Dan may not have the money to be throwing the parties, but he sure knows how to pine after a girl who’s out of his reach. Combining characteristics of real life author F. Scott Fitzgerald with some of his famous hero from The Great Gatsby, Gossip Girl gives us the ultimate pining, angsty writer boy.

Roman Holiday

Blair is finally about to become a princess, and she’s riding off into the sunset with her dream Prince Louis. With a bob cut, a moped, and a handsome escort, Blair’s off to recreate one of the most iconic scenes from the movie that won Audrey Hepburn an Academy Award. But just like Princess Ann, Blair’s Roman holiday is about to get cut short – when her handsome fiancé morphs into her old love Chuck Bass.

All About Eve…or in This Case, Vanessa

Before Mean Girls, there was All About Eve, the story of an aging actress who takes a budding young actress named Eve under her wing – only to have Eve turn on her and begin to steal her place in the spotlight. Blair is all too familiar with this sense of jealousy and betrayal – only in this case, she’s being shown up by her nemesis Vanessa, who is the opposite of Blair in every way.

Sabrina

While I’ve got a soft spot for the Harrison Ford remake of this classic, it’s all about Hepburn and Bogart for Chuck and Blair. This is a recreation of the tennis court scene in the original 1954 romance Sabrina, where Humphrey Bogart woos Audrey Hepburn’s Sabrina in an attempt to keep her away from his younger brother David. Chuck is trying to keep Blair away from someone too – the charming Prince Louis – but the best part of this recreation is just how perfectly Leighton Meester can bring every classic Hepburn look to life.

Charade’s Up for Blair Waldorf

Blair is having a splendid evening with Chuck, and they start playing a party game with other guests at the nightclub they’re in – passing an orange without using their hands. But when Blair tries to pass on the orange to the next guest, it turns out to be Chuck’s murderous father. 

Did this scene feel a little weird? Well, it’s from a ‘60s comedy/romance/murder mystery called Charade – a weird combination of elements that somehow works. I can’t describe how delighted I was to see this reference, because it’s another Hepburn classic that gets much less attention than Breakfast at Tiffany’s does. It’s a final homage to Blair’s love for Hepburn, and a fitting one at that.

Don’t Forget about the Episode Titles

The final Easter egg starts the soonest in the series – with the show’s second episode. “The Wild Brunch” is episode 2’s title, and it’s a play on the 1969 Western film The Wild Bunch. Whether the episode title has any direct relation to the plot of the episode or not, nearly every episode title is a direct play on the title of some classic film or show. Just read the list and see how many you can guess for fun. My favorite is season 4, episode 15: “It-Girl Happened One Night.”