The 9 Best Musical Moments From ‘Gossip Girl’

Justin Timberlake, Lady Gaga and a whole lot of teen drama.

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Gossip Girl isn’t necessarily a great show — it’s problematic, to say the least, in regards to its depictions of literally every character that isn’t a rich white person, it’s terrible with plotting, and Ivanka Trump had not one, but two cameos across the series — but it’s a show that was important for the teen canon. While the quality of the Upper East Side melodrama may have waned over its six seasons, one thing — the soundtrack — remained consistent.

Compiled by Alexandra Patsavas — perhaps the most famous music supervisor ever and the woman responsible for the Twilight, O.C., Grey’s Anatomy and Hunger Games soundtracks, among others — the show’s music was a reflection of its time and place. It oscillates between little-known indie-rock (Brisbane’s Ball Park Music scored a sync with a song from their debut album way back in 2011) and mainstream pop music (Jason Derulo’s ‘Whatcha Say’ soundtracks a particularly heated Thanksgiving lunch).

Patsavas’ decision to pick and choose from both sides of the indie/mainstream divide that was so present in the mid-2000s was savvy — she understood that Gossip Girl’s audience was part of a generation for whom genre classifications would mean basically nothing. Looking at a list of songs from any given Gossip Girl episode is like looking at a curated Spotify playlist: the songs are stylistically disparate, but they work as a whole.

2017 marks ten years since Gossip Girl premiered and in honour, we’ve collected 9 of the best musical moments from the show (with a hat tip to the very dedicated YouTube channel that’s catalogued a whole 79 of these).

Serena arrives back in Manhattan

Season 1, Episode 1
Song: ‘What Goes Around…Comes Around’ — Justin Timberlake

Gossip Girl’s pilot is an incredible exercise in setting up tensions that unravel for the rest of the season (and series, for that matter).

This scene — Serena’s entrance back into the Upper East Side social scene — establishes Blair’s estrangement from her best friend, Nate’s latent attraction to her, and Serena’s disillusionment with the UES clique and her mother. Justin Timberlake’s bitter breakup anthem ‘What Goes Around … Comes Around’ fits the mood perfectly, Blair’s obvious horror at the prospect of Serena’s return mirrored in the song.

Blair confesses her hookup with Chuck to a priest

Season 1, Episode 8
Song: ‘One Week of Danger (Demo)’ — The Virgins

Chuck and Blair’s romance is one of the most fraught parts of Gossip Girl, but some of the syncs in the Chuck/Blair scenes are killer. This one, a demo of a song by New York band The Virgins, became instantly iconic after a few seconds (literally a few seconds) of it were used in this episode.

YouTube is littered with fan-made compilations of Chuck and Blair scenes set to the song. It makes sense that this — as opposed to any other of the hundreds of songs used in Gossip Girl — has become the couple’s calling card. It’s scuzzy, secretive, and the lyrics, a series of vaguely sexist come-ons, seem to describe Chuck and Blair’s relationship to a tee. It’s also bland as hell, and hard to listen to in full — again, reflective of Chuck and Blair’s relationship.

Blair ruins Georgina’s life

Season 1, Episode 18
Song: ‘Do You Wanna’ — The Kooks

After a few episodes worth of manipulation and scheming, Georgina Sparks — a recurring antagonist in the series — gets the first of many Blair Waldorf-orchestrated comeuppances in the series. The Kooks’ ‘Do You Wanna’ soundtracks the scene, Luke Pritchard’s vocals slowly becoming more and more manic as Georgina realises her fate. The song starts to wig out right as Blair delivers a classic Waldorf zinger: “Haven’t you heard? I’m the crazy bitch around here.”

Serena and Nate kiss at the White Party

Season 2, Episode 1
Song: ‘Paparazzi’ — Lady Gaga

Season 2’s White Party is well-remembered as one of Gossip Girl’s best set pieces, for good reason: set in the Hamptons during summer, it looks great, and it also sets up one of GG sauciest plot lines — Nate’s love triangle with Vanessa and married socialite Catherine Beaton, the stepmother of Blair’s boyfriend Lord Marcus Beaton, who is also having an affair with Catherine. His stepmother. Did you catch all that? It’s bonkers! And the stepmother is played by Madchen Amick from Twin Peaks! It’s wild!

This scene, where Serena kisses Nate to make Catherine jealous, before being seen by her ex-boyfriend Dan, is a classic — Lady Gaga’s ‘Paparazzi’, which underscores the scene, swells as Nate and Serena are seen pashing, and suddenly cuts as soon as Dan appears. Drama, drama, drama.

Serena becomes Queen of Constance and Dan goes back to being a nobody

Season 2, Episode 4
Song: ‘Shove It’ — Santigold

The final scene of Season 2, Episode 4 is a doozy — after he dares to go on a date with the new transfer student, Dan finds himself back at the bottom of the social pyramid, with his once benevolent ex Serena back on top and as cruel as ever. Santigold’s schoolyard chant of “We think you’re a joke” is nasty and beautiful, and makes up for Serena’s subtlety as she shakes her head at Dan and walks away.

Fights break out at Thanksgiving

Season 3, Episode 11
Song: ‘Whatcha Say’ — Jason Derulo

This season 3 Thanksgiving lunch is the most openly soap opera-y scene in Gossip Girl‘s entire series: set to Jason Derulo’s ‘Whatcha Say’, multiple conflicts break out along the Van Der Woodsen dining table before dinner’s even begun.

Rufus finds out Lily has been lying to him about her mysterious trip a few months earlier; Blair thinks her mother is pregnant; Jenny is angry at Eric for sabotaging her cotillion; Vanessa hates her estranged mum for being a terrible parent; and — my personal favourite — Serena gets blackmailed by the wife of Nate’s cousin Tripp, a congressman that she’s having an affair with. Believe it or not, this is actually one of the less convoluted plotlines from season 3.

Chuck falls from grace

Season 4, Episode 20
Song: ‘Ladder Song’ — Conor Oberst

(CW: domestic violence)

In one of Gossip Girl’s more problematic scenes, Chuck, drunk, smashes a window after Blair tells him they can’t be together. Chuck is the show’s most vile character: he’s abusive and manipulative from the first episode.

Gossip Girl’s ultimate failing is that it never problematises Chuck’s behaviour at all; instead, his abusive behaviour is used as impetus for his ‘redemption arc’, and Blair goes back to him unquestioningly. Conor Oberst’s ‘Ladder Song’ soundtracks the scene, its lyrics almost seeming to reference Blair’s bittersweet split from Chuck: “Kiss the feet of a charlatan / some imagined freedom”.

Chuck apologises to Blair

Season 5, Episode 6
Song: ‘Video Games’ — Lana Del Rey

And then Chuck apologises, and all is forgiven! Like I said, Gossip Girl never forces Chuck to truly acknowledge the heinousness of his behaviour.

It’s especially disappointing because the show presents Blair and Chuck as its Great Romance, and it’s the relationship that most fans were emotionally invested in throughout the run. Set to Lana Del Rey’s ‘Video Games’ — fittingly, a song about devotion to a damaging partner — the scene presents Chuck’s speech as a Big Romantic Gesture; realistically, it’s nothing.

Dan reveals he’s been playing Serena

Season 6, Episode 7
Song: ‘Kill For Love’ — Chromatics

At the midpoint of season 6, Dan and Serena are finally back together and it seems like everything’s pretty smooth sailing — until Dan reveals to Georgina that he’s only dating Serena again so he can write a scathing essay about her for Vanity Fair, as he’s done to all his other friends.

As Chromatics’ Ruth Radlet sings in the beginning of the song — “Everybody’s got a secret to hide”. The way ‘Kill For Love’ is used in this scene is typical of how Gossip Girl likes to end episodes, with the song peaking right as a final twist is revealed.

Shaad D’Souza is a freelance writer from Melbourne. Follow him on Twitter here.