The 20 Best Episodes of ‘Gossip Girl’

  • Dec 17, 2012
  • Buddy TV

As the series finale of Gossip Girl approaches, it’s time to take a look at the stellar episodes we’ve had the pleasure of watching along the way. Just like Gossip Girl herself, we’ve been witness to all the schemes and backstabbing, as well as a dizzying amount of breakups and makeups. From secret British lords and royal weddings, to limo stalking and dips in Parisian fountains, here are the 20 best episodes of Gossip Girl in very unscientific order.


#20 “The Revengers”

Season 6, Episode 9: I initially couldn’t decide if this melodramatic, insanely soapy installment should make the list. But you have to give respect to a show that throws caution to the wind…and throws Bart Bass off a building. In by far one of the most insane episodes Gossip Girl has ever aired, Chuck lets cartoon villain Bart drop off a building, Nate goes to jail, and Blair forms a fabulous bitch brigade. Some great Chuck and Blair as well as Blair and Serena scenes give the episode some emotional stakes, but mostly it’s just so insane you have to respect it’s commitment.


#19 “G.G.”

Season 5, Episode 13: Gossip Girl’s fifth season was a dismal time for the show. Blair remembered her pact with God but forgot she had been pregnant, there were dowries like the show took place in the 16th century, Louis was in almost every episode, and Dan’s hair began to take on sentient life. But for Gossip Girl’s 100th episode, the show pulled it together to make a show-stopping episode involving a wedding, a damaging Gossip Girl blast, a runaway bride, and Georgina dressed as clergy. And that isn’t even mentioning the Marilyn-Audrey dream sequence.


#18 “Raiders of the Lost Art”

Season 5, Episode 22: In this episode, which I lovingly refer to as the ‘haunted house orgy’ episode, Chuck discovers Bart is actually alive. “Got you, son!” “Not for long dad!” Meanwhile Elizabeth Hurley actually factors into the overall plot, Blair finds out Serena was Gossip Girl and everyone schemes together like a well-oiled machine until they end up at a creepy sex club. Everyone knows on Gossip Girl it’s not really a good scheme unless hookers are involved.


#17 “Gone Maybe Gone”

Season 6, Episode 1: It’s a few months later and everyone realizes “Oh whoops, I think we misplaced Serena!” So the whole gang goes on a road trip to find Serena and bring her back to her rightful place on the Upper East Side. Meanwhile the dysfunctional literary duo of Dan and Georgina meet up with the group on the way, and everyone ruins the lovely wedding of a gay couple. It’s a fun episode that manages to avoid getting mired in some of the ludicrous plotlines and Evil Bart Bingo which dominates the rest of the season.


#16 “The Treasure of Serena Madre”

Season 3, Episode 11: Gossip Girl loves Thanksgiving, and in this turkey day classic everything goes to hell in a handbasket quicker than you can say ‘Cece loves gin’. Serena carries on her illicit relationship with married senator Tripp, while Nate carries a torch once more for Serena. Rufus and Lily have some more relationship nonsense, while Blair tries to get her mother to drop a big secret. It all culminates in a fantastic dinner table scene that is furiously fast and hilarious. Gin for everyone!

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#15 “War at the Roses”

Season 4, Episode 7: Coming off another Blair and Chuck war, Nate and Serena do the only thing two reasonable semi-adults can: they make them sign a literal peace treaty. With a notary involved! But if Blair and Chuck aren’t fighting, it turns out they just end up having hate sex on pianos. Meanwhile, Dan goes insane for questionable reasons and teams up with confused Swedish pop singer Robyn to unveil Blair’s darkest secret. Considering that Blair has literally banished people from Manhattan before, it’s even funnier when her darkest secret turns out to be bad karaoke.


#14 “Witches of Bushwick”

Season 4, Episode 9: The beginning of the fourth season was a very strongly plotted, enjoyable moment for the show. This episode saw the nightmare team of Jenny, Vanessa, and Juliet form to take down Serena. Meanwhile Serena tries to chose between Nate and Dan but finds it hard, while Blair and Chuck reunite for one steamy, dramatic moment at the Saints and Sinners party. Were there any saints at that party? Everyone knows the Upper East Side if full of sinners.


#13 “O Brother, Where Bart Thou?”

Season 2, Episode 13: When Bart “dies” for the first time, Chuck is much more distressed than he was the second time around. In fact, Chuck spends much of this episode looking like he’s transitioning into a vampire or hasn’t stepped foot in the sun for a century. Grief can do that to you. Blair finally gives in and admits her love for Chuck, but he just isn’t ready to hear it yet despite their tearful hug. And as death looms all around, Lily and Rufus decide it’s time for romance and Eleanor makes an honest man out of Cyrus. Not enough!


#12 “The Debarted”

Season 3, Episode 12: Gossip Girl really loves it’s Bart pun titles doesn’t it? In this great season three episode, Serena is nearly killed by wolves because…why not? There are moments so perfectly preposterous that they live on in your memory forever: Serena’s near death-by-wolves is one of them. Meanwhile Chuck faces the demons of his father’s death for the 50th time, but it results in a sweet scene with Blair in the hospital. “You carry people. You carry me,” she tells him as a beautiful M83 song plays in the background. And Nate fulfills his purpose on this show by punching someone in the face.


#11 “The Goodbye Gossip Girl”

Season 2, Episode 25: The gang graduates from high school, while Blair crowns Jenny queen with a literal gem-studded headband. But perhaps the most memorable moment of the episode came as Blair and Chuck finally exchanged those three words with eight letters as the camera swoops around them from above. Also Serena declares the first of her many and varied wars on Gossip Girl, but decides to run off with Carter Baizen instead, which is a solid choice.

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#10 “The Thin Line Between Chuck and Nate”

Season 1, Episode 13: In the season one mid-season finale, things finally come to a head with the Nate-Blair-Chuck love triangle. Jenny Humphrey ascends the Constance Queen Bee throne and Serena convinces a fleeing Blair to stay and fight for her crown. This episode brought together all the plot threads from the first batch of episodes and promised one heck of a catfight for the crown when the show returned.


#9 “Enough about Eve”

Season 3, Episode 6: Perhaps this episode wouldn’t make it to the top of everyone’s favorite episode list, but I loved how zippy and fun it was. Blair whores Chuck out for fun, profit, and social standing…and to a man no less. That’s usually Nate’s job! Meanwhile Nate and Serena team up together to become the most inept pair of high stakes gamblers the world has ever seen.


#8 “Blair Waldorf Must Pie”

Season 1, Episode 9: Gossip Girl loves it’s Thanksgiving episodes. Some of the show’s best episodes have taken place around a Thanksgiving table as everyone schemes and betrays everyone else. The mood was certainly set during this first Thanksgiving episode, when the truth about Lily and Rufus’ romantic past emerges. This family-centered episode also most directly deals with Blair’s eating disorder and her complicated relationship with both of her parents.


#7 “Belles Du Jour” and “Double Identity”

Season 4, Episode 1 and 2: This might technically be cheating, but I don’t care. Both episodes of Blair and Serena flouncing around Paris and pushing each other into fountains were great delights. Having the show really film in Paris allowed these episodes to be both narratively fun and visually stunning. The moment when Blair finds Chuck in her beautiful gown at the train station is a feast for the eyes and a beautifully emotional scene thanks to fine work from Meester and Westwick.


#6 “Hi, Society”

Season 1, Episode 10: What do you get when you take The Pierces, Carter Baizen, Grandma CeCe, formal wear, a failed Chuck scheme and add them together? You get this fantastic episode from the first season, when Blair and Serena come out at Cotillion only for everything to go both wrong and right simultaneously. This was a truly excellent and masterfully plotted episode and yet it would have made the list regardless of it’s artistic merits just on the basis of that hilarious wink Nate shoots Chuck. Oh Nate, you precious snowflake.


#5 “New Haven Can Wait”

Season 2, Episode 6: This great episode from season two could have made the list on the strength of Blair and Serena’s hilarious catfight alone. “I hate that stupid headband!” Serena yells as she rips Blair’s signature piece off and flings it away. But the episode really merits it’s place on the list by providing some great Blair and Serena material. Plus Chuck is kidnapped by a secret society, Nate punches some faces as usual, and Dan ends up tied to a pole in his boxers

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#4 “All About My Brother”

Season 1, Episode 16: It’s always great when Gossip Girl herself plays a prominent part in the episode, like she did in this late season 1 outing. This episode, in which Georgina outs Eric, Blair takes down Jenny, and Serena admits that she killed someone, never really stopped to take a breath of air. It was a great episode because, like the best episodes of this show, all the storylines were woven seamlessly together to make for one chaotic dose of scheming, betrayal, and the ultimate OMG ending.


#3 “The Age of Dissonance”

Season 2, Episode 18: Like an onion or Chuck’s multiple popped collars, this episode had many layers and intricacies. The most striking was the staging of Edith Wharton’s “The Age of Innocence,” which was in turned mirrored by the lives of our favorite Upper East Siders. Gossip Girl owes a lot to it’s literary allusions and Edith Wharton has more fingerprints on the show than any other source material. So it was great to see the show pay tribute to the ultimate teller of social hierarchy tales, while spinning it’s own yarn from Wharton’s pattern.


#2 “Bad News Blair”

Season 1, Episode 4: While the opening episodes of Gossip Girl’s first season were full of fun catfights and wild parties, the show didn’t truly find it’s heart until Blair read Serena her letter at the end of episode three. “Bad News Blair” finally begins to explore the thorny, special, and complicated friendship between our two main frenemies. Serena will always get the thing that Blair wants without even trying, and Blair will always try to hold onto what she wants so hard it will ultimately slip her grasp. Besides some great fashion, including the photoshoot outfits and Chuck’s insane basketball attire, this episode was one of the first to establish the softer sides of both Blair and Chuck.


#1 “Summer, Kind of Wonderful”

Season 2, Episode 1: Whenever I think about my favorite episode of Gossip Girl, I always come back to the pastel-hued perfection of the season two premiere. This episode really is the perfect encapsulation of Gossip Girl firing on all creative cylinders. The clothing is beautiful and sort of ridiculous. The emotional stakes are real and the multiple face-offs between Blair and Chuck are beautifully shot and acted. Serena has the most stunning hair of any living human being. Plus the episode also sports some of the hands-down funniest things the show has ever done. If there’s a TV moment funnier than Marcus outing himself as a British Lord, complete with fade-in accent, I haven’t seen it yet.

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