On September 19, 2007, Gossip Girl introduced the world to the elite lives of Manhattan’s young and ruthless. Over six seasons, it gave us high fashion, outrageous plot twists, and a narrator whose omniscient presence became as iconic as the cast itself.
To celebrate its 18th anniversary, we’re looking back at the 10 most iconic episodes of all time. The ones that changed everything, went viral before viral was a thing, and kept us glued to our screens.
Spoilers ahead!
Victor, Victrola (Season 1, Episode 7)
IMDb
Possibly the best episode of the series, thanks to the beginning of Chuck and Blair’s story. This was the episode that transformed Gossip Girl from a fun teen drama into a full-blown obsession. Victor, Victrola gave us the steamy limo scene between Chuck and Blair; the start of one of the most beloved (and chaotic) TV pairings of the 2000s. While earlier episodes hinted at Chuck’s bad-boy image, this one added unexpected depth and vulnerability to his character. Blair’s decision to let loose and embrace her own desires was a defining turning point. From that moment on, “Chair” was born.
Blair Waldorf Must Pie! (Season 1, Episode 9)
Gossip Girl – HBO
This Thanksgiving episode gave Gossip Girl its first real emotional weight. Beneath the designer coats and snarky dialogue, the characters revealed their vulnerability, particularly Blair, whose perfectionism cracks under the weight of her eating disorder and strained relationship with her mother. Meanwhile, Serena confronts her traumatic past, and Rufus and Lily’s unresolved chemistry simmers over dinner. The juxtaposition of Upper East Side glitz with raw, personal drama made this episode unforgettable.
The Goodbye Gossip Girl (Season 2, Episode 25)
HBO
This explosive Season 2 finale marked a turning point for nearly every major character and for Gossip Girl herself. As the gang graduates from high school, the mysterious blogger launches a brutal final attack, exposing secrets that almost destroy friendships and reputations. Blair and Chuck’s long-awaited “I love you” moment finally happens, giving fans the emotional payoff they’d waited for. The episode also raises the stakes for Season 3, showing that even as the characters move on from Constance and St. Jude’s, Gossip Girl still has the power to control their lives. A perfect storm of drama, romance, and mystery.
G.G. (Season 5, Episode 13)
IMDb / GIOVANNI RUFINO – © ©2011 THE CW NETWORK, LLC
Released as the show’s 100th episode, it had it all: heartbreak, high fashion, and a shocking twist that rocked the fandom. Set at Blair’s royal wedding to Prince Louis, G.G. delivered some of the show’s most unforgettable moments, including Chuck and Blair’s emotional confrontation, Serena’s sabotage, and Blair fleeing her own wedding in a paparazzi frenzy. Also, the final minutes, when Georgina dramatically reveals she’s Gossip Girl (or so it seems).
The Townie (Season 4, Episode 11)
IMDb
The Townie is often overlooked, but for true fans, it’s one of the most pivotal and darkest episodes of the series. Blair and Dan team up for a rare alliance, digging into Juliet’s sinister backstory and uncovering her role in Serena’s forced institutionalization. It’s a noir-inspired detour with thriller energy, giving both characters a break from romance and a chance to show their brains. The team-up also plants the early seeds of their eventual relationship. With tension, mystery, and a satisfying unraveling of a major subplot.
New York, I Love You XOXO (Season 6, Episode 10)
IMDb / Giovanni Rufino – © 2012 THE CW Network, LLC.
After six seasons of secrets, scandals, and schemes, Gossip Girl finally revealed her identity and few could’ve predicted it. In a jaw-dropping twist, it is unmasked the blogger who’d been narrating (and manipulating) their lives all along. The episode also gives fans long-awaited closure: Chuck and Blair get married in a quick, high-stakes ceremony, Serena reads Dan’s manuscript detailing his twisted love story, and a flash-forward shows everyone five years later.
Roman Holiday (Season 1, Episode 11)
IMDb
Christmas on the Upper East Side is never peaceful, and Roman Holiday proves it. This episode is iconic for introducing Blair’s father, Harold, and his new boyfriend Roman, whose presence completely upends Blair’s holiday plans. As she struggles to accept her father’s new life, we see a more vulnerable, deeply personal side of her. Meanwhile, Serena and Dan exchange heartfelt gifts, and Jenny begins her long-running habit of scheming to climb the social ladder.
Last Tango, Then Paris (Season 3, Episode 22)
HBO
Few Gossip Girl episodes packed the emotional punch and controversy of the Season 3 finale. Last Tango, Then Paris is infamous for the heart-wrenching fallout between Chuck and Blair, who had just been on the verge of reuniting. After discovering that Chuck had traded her for a hotel earlier in the season, Blair finally begins to move on. Meanwhile, Serena’s romantic indecision causes chaos, Jenny hits rock bottom after sleeping with Chuck (a twist that infuriated fans), and Dan punches Chuck. Blair kicks out Jenny of Manhattan. It’s dramatic, dark, and deeply polarizing: the kind of finale that had fans spiraling for an entire summer. Whether you loved it or hated it, there’s no denying this episode left a mark.
Pilot (Season 1, Episode 1)
The Gossip Girl pilot didn’t just introduce viewers to Manhattan’s elite; it threw them headfirst into a glittering world of secrets, status, and scandal. From Serena’s mysterious return to Blair’s simmering jealousy, Dan’s outsider charm, and Nate’s inner conflict, the show wasted no time establishing its core tensions. And, of course, we got our first taste of Kristen Bell’s iconic narration, a voice that would become pop culture canon.
The Thin Line Between Chuck and Nate (Season 1, Episode 13)
HBO
This episode is peak Gossip Girl: full of betrayal, drama, fashion, and the moment the show truly found its voice. After weeks of scheming and tension, Blair’s world comes crashing down when her biggest secret (that she slept with Chuck) is exposed to the entire school via a Gossip Girl blast and Nate finds out. She’s dethroned from her queen bee status, humiliated by her classmates, and publicly shamed in a way that felt both brutal and unforgettable. Meanwhile, Chuck becomes the ultimate villain, watching Blair fall from grace with cold satisfaction, while Serena and Dan continue to navigate their messy, star-crossed relationship.
