Gossip Girl here, and she’s bringing in the latest news straight from the Upper East Side. Over six seasons, television would never be the same again, thanks to the ultra-fab and uber-rich of New York City. But daddy’s money has its consequences. A wad of Benjamins could easily buy fame and friends, but no amount of cash can save someone from the wrath of Gossip Girl.
Although the supposedly teen series may have earned its notoriety because of how it glamorizes underage drinking and excessive behavior, some episodes refreshingly stood out from the usual hedonistic escapades. Without further ado, here are the 10 best Gossip Girl episodes, ranked.
10
“Pilot”
Season 1, Episode 1 (2007)
The original Queen Bee, Serena van der Woodsen (Blake Lively), finally returns to New York after mysteriously moving to Connecticut for boarding school. Her old circle is shocked at her abrupt appearance, but none more so than her “best friend” Blair Waldorf (Leighton Meester). Blair feels threatened after discovering Serena once slept with her boyfriend, Nate Archibald (Chace Crawford). Outcasts Dan (Penn Badgley) and Jenny Humphrey (Taylor Momsen) try to find their place amongst the Upper East Side elite.
It can get tricky navigating the fluctuating social dynamics of the Upper East Side, but the show’s premiere episode lays down the groundwork well. Apart from setting the tone for Gossip Girl, the pilot episode does an exceptional job of establishing who the characters are and the relationships they share. It also strikes the right balance of drama, shock value, and nuance, preventing characters from being stuck in the wealthy-working-class binary, and showing that no matter how much wealth you accumulate, there will always be problems.
9
“The Wrong Goodbye”
Season 4, Episode 22 (2011)
As the aftermath of Blair’s accident slowly reveals itself, Chuck helps her through trauma. Whatever Blair wants, she gets. Serena admits her mistakes and reconciles with Blair, while Nate pursues a new media-driven path. Charlie’s secret identity is blown, causing a commotion among the family. As all of this is happening, Dan tries to figure out his true feelings for Blair.
It’s easy to use chaos as a shock value, but “The Wrong Goodbye” proves that emotional weight is just as powerful a tool. Chuck and Blair’s night spirals from danger to passion, only to end in sacrifice as Chuck lets her go. Meanwhile, Serena takes real ownership of her choices, while Dan’s secret manuscript threatens to uproot his place among the Upper East Side’s elite.
8
“Much ‘I Do’ About Nothing”
Season 1, Episode 18 (2008)
Georgina tries to ruin Serena by exposing her past, but Serena decides to tell Dan the truth about accidentally killing someone. Dan feels betrayed by the mess Serena puts him into and breaks things off with her. Blair finally reunites with Chuck, but he runs away in fear of commitment. Rufus confesses his feelings to Lily, but she chooses to go through with her wedding to Bart.
Before “Much ‘I Do’ About Nothing,” Georgina (played by Michelle Trachtenberg) has been latching onto Serena and the gang like a parasite, waiting for the right moment to suck them dry. Serena could barely do anything about it — after all, she was there when Georgina got someone killed. But for the first time, Blair and Dan team up to pull off a devilish revenge scheme. Surprising for Dan, but for Blair, it’s just another normal day.
7
“The Dark Night”
Season 2, Episode 3 (2008)
A citywide blackout puts a glamorous party on hold. Dan tries to patch things up with Serena, but they just can’t seem to get their messages across without getting riled up. Nate hides his affair with Catherine, but Vanessa pressures him for the truth, leading to a painfully honest moment between them. Blair is frustrated that her future husband cannot fulfill her more intimate needs. Chuck, however, still knows what Blair likes.
The real main character of “The Dark Night” is the blackout itself. With one of their basic needs stripped off against their will, these Upper East Siders are completely vulnerable in pitch black darkness. Everyone’s forced to confront their own fears and secrets. By the time the lights are back on, so is their conscience.
6
“The Debarted”
Season 3, Episode 12 (2009)
On the anniversary of Bart’s death, Chuck struggles to cope with his mounting grief, most of which stems from a sense of guilt. Blair tries to support him, but he resists. Eventually, the more he keeps to himself, the more emotions he piles up, leading to an intense emotional breakdown. As for Serena and Nate, the two are caught up in an unwanted situation when the former experiences a near-fatal crash, no thanks to Nate’s careless cousin.
“The Debarted” strips Chuck’s glossy facade and reveals his true nature: he’s soft (and actually has an interesting arc in Gossip Girl). But Chuck, being Chuck, is walking on a tightrope between putting up a steel front and being broken from loss. But Blair proves she’s the only one who can cut through the armor. No matter how hard-headed Chuck and Blair can be, the two always have each other’s backs.
5
“Victor/Victrola”
Season 1, Episode 7 (2007)
Chuck tries to be his own man in the business world, only to be undermined by his rags-to-riches business magnate father. No matter how many times Blair tries to convince him, Nate finally admits that he never loved her. Heartbroken, Blair acts recklessly at Chuck’s new burlesque club, where the two eventually catch feelings for each other in the back of a limousine. Meanwhile, Serena and Dan are trying to be more open about their relationship, while Jenny finds herself dismissed by Blair after telling her some painful truths.
Addison Rae once sang, “Losing all my innocence in the back seat,” — which truly describes the ending of “Victor, Victrola.” Previously, Blair and Chuck were never the obvious couple, and she certainly had no intention of losing her virginity to him. They were, however, constantly butting heads with their sharp opinions and their shared love of unadulterated scheming. This episode is just the beginning of the two’s tumultuous yet entertaining relationship, and there’s still more to come.
4
“Last Tango, Then Paris”
Season 3, Episode 22 (2010)
“Last Tango, Then Paris,” is a never-ending chain reaction of plot twists that ends in an explosion. Jenny snaps a photo of Dan and Serena asleep together. Blair, after going back and forth with her feelings, chooses Chuck — only to discover he’s slept with Jenny moments before their reunion. Jenny is exiled to Hudson, Serena ditches Nate for Paris with Blair, and Georgina crashes in with news of her pregnancy — with Dan’s baby.
Just as things couldn’t get any worse for these flawed characters, “Last Tango, Then Paris,” shows them at their lowest. Ironically, this makes it one of the best episodes of the drama series, simply because everyone’s worst impulses collide. What makes the finale even more unapologizing is how cruelly timed the betrayals are. Jenny’s desperate attempt to matter costs her everything, while Chuck sabotages his own happiness at the brink of redemption.
3
“The Goodbye Gossip Girl”
Season 2, Episode 25 (2009)
With their togas on and their diplomas ready, “The Goodbye Gossip Girl” is the quintessential high school graduation episode. But when it comes to the Upper East Siders, Gossip Girl is crashing the party. The notorious blog goes on a blast, branding Serena “irrelevant,” Blair “weak,” Dan “an insider,” Nate “whore,” and Chuck “a coward.” Serena vows to take Gossip Girl down, only to learn that they’re the reason why the site exists in the first place.
Even at their highest triumph in their teenage school lives, Gossip Girl shows no mercy. The site isn’t afraid to lay out all the tea, pointing out Serena’s fear of irrelevance, Blair’s desperation for Chuck’s love, and Dan’s denial of becoming “one of them.” Instead of letting them go, Gossip Girl proves she’s coming with them to college.
2
“The End of the Affair?”
Season 5, Episode 11 (2012)
“The End of the Affair?” jumps between present-day suspicion and flashbacks of the car crash aftermath. Chuck struggles to understand why Blair has suddenly cut him off, while Louis suspects an affair and drags Chuck into investigating her. Meanwhile, Blair is secretly leaning on Dan, who helps her hide late-night outings and her emotional breakdowns.
Gossip Girl has seen Blair making the wildest choices, but none compare to the one in this episode. Blair made a desperate promise to God at the hospital: if Chuck survived his near-fatal injuries, she would marry Louis. What looks like betrayal is really self-sacrifice in this Gossip Girl storyline. She loves Chuck so much, she’s willing to chain herself to Louis for his survival. Chuck, being the stubborn guy he is, isn’t going to let Blair off the hook without answers.
1
“New York, I Love You XOXO”
Season 6, Episode 10 (2012)
“New York, I Love You XOXO” doesn’t skimp on the shocking chaos. Bart, who faked his death back in Season 2, falls to his death after a confrontation with his own son. This leaves Chuck and Blair fugitives until Jack pushes them to marry under spousal privilege. Meanwhile, Dan slips Serena his final chapter, which reveals he has been Gossip Girl all along.
It’s the conclusion everyone has been waiting six seasons for. While viewers have their own positive and negative spins about Dan being Gossip Girl this whole time, it is still a surprising revelation, nonetheless. The series also ends on a bittersweet note. Flash forward five years, everyone’s back and happy in Blair’s apartment — even Jenny — to witness Serena and Dan tying the knot.
