The arrival ofGossip Girlon the CW in 2007 helped to change the face of the network and the best episodes ofGossip Girlare a big part of that change. During the late 2000s,Gossip Girlruled the CW, allowing soapy dramas, characters with designer clothing, and schemes that involved double-crossing best friends to be the hallmarks of the shows airing at the time.
Gossip Girlwas inspired by the book series of the same name. It followed a group of mostly wealthy teenagers, and later, college students, who lived in the Upper East Side. Their lives were plagued by a mysterious blogger known only asGossip Girlwho always seemed to be one step ahead of them. The show was so scandalous that it had parents calling for boycotts of the network, but it was the kind of show people just could not stop watching. HBO attempted to repeat the interest with a revival series in 2021, but it just did not capture the same lightning in a bottle that these episodes did.
10Pilot
Season 1, Episode 1
…right out of the gate the show demonstrated how scandalous it would be…
Pilot episodes can be difficult to assess when it comes to looking back on a series as a whole. That’s because pilots are largely filmed as a way to sell the concept of a show to a network and give brief overviews of the main characters rather than tell a complete story. That means that by the end of a show, fans love just about every other episode besides the pilot. That is not the case withGossip Girlbecause right out of the gate the show demonstrated how scandalous it would be and how much betrayal would be happening among the main cast.
Thefirst episode ofGossip Girlsees Serena return home after spending some time at boarding school. Serena seems relatively sedate compared to a lot of the characters around her in the pilot episode, so the audience spends a lot of time wondering how she could be the “wild child” of the show until it’s revealed that she hooked up with her best friend’s boyfriend.
This episode encapsulates what season 1 of the show is all about. It introduces all of the major players in all of the big scandals, giving hints at which characters have the most chemistry and setting up some long-running storylines.It’s a fantastic way to kick off the series, even if there are a few items that are changed, like Chuck and Nate taking public transportation to school when they would later have their own drivers.
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9New York, I Love You XOXO
Season 6, Episode 10
For many fans, series finales are bittersweet. There’s an excitement about seeing storylines tied up, but there’s also the dread of saying goodbye to the characters they love.TheGossip Girlseries finale is certainly bittersweet, but it also runs through its story at a breakneck speed as secrets are revealed, and one last scandal has to be avoided.
Of course, the biggest takeaway from the finale is Gossip Girl’s identity being revealed to be someone almost none of the audience suspected. It’s one last big twist for the audience to analyze, even years later, because it changes a lot of what the audience knows about Dan Humphrey whenall of his actions as Gossip Girlare put in perspective.
Not all fans of the show love the finale, but it’s certainly right in line with all of the drama they would expect from the entire run of the show. It also brings some of the characters to the next logical step in their lives as careers are decided on and marriages are formed.
8The Treasure Of Serena Madre
Season 3, Episode 11
While the glamour of big society functions in the show is fun,Gossip Girl’ssecret weapon is actually its Thanksgiving episodes.The show has a handful of them, and two of them are among the best episodes of the show of all time, including this one.
The Thanksgiving episodes often draw together characters from vastly different areas of the show and always spill huge secrets that the characters have tried to keep hidden.In this case, the big story of the episode is Serena trying to keep her affair with her older and married boss a secret. Unfortunately for her, Serena’s own mother happens to invite the man’s wife to Thanksgiving dinner before she realizes what her daughter has been up to.
The episode (and dinner) devolves into pure chaos as Lily discovers Serena’s secret. It all comes together with Jason Derulo’s “Whatcha Say” playing over the dinner table.It’s bothGossip Girlat its soapiest and its funniest.
7The Age Of Dissonance
Season 2, Episode 18
Gossip Girlusually excels with drama, but this one will have fans crying tears of laughter instead.
When fans of the show discuss the best episodes ofGossip Girl, “The Age of Dissonance” often gets overlooked.It’s an underrated gem in Gossip Girl’s 100+ episodes because it is not like so many other episodes.Gossip Girlrarely works social commentary into its show, instead preferring to simply get as scandalous as it can for the audience. Here, however, it does.
The students at Blair and Serena’s prep school are putting on a play based on Edith Wharton’sThe Age of Innocence(hence the episode title), but everyone is so wrapped up in their own drama that they do not actually care as much about the play as it would appear. While Serena is busy trying to get the attention of the famous director in charge of the play, Blair is on the warpath because she did not get into her dream college.
Ultimately, everyone quite literally attacks one another on stage while in the middle of the play due to their own selfishness. The play ends up being praised for its meta take on the content, and the entire outing makes for one ofGossip Girl’sfunniest episodes ever.Gossip Girlusually excels with drama, but this one will have fans crying tears of laughter instead.
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6The Townie
Season 4, Episode 11
There are a lot of episodes that take the show out of Manhattan, but when that happens, it’s usually because Blair and/or Serena have jet-setted somewhere in Europe. That’s not what happens here. Instead, Blair and Dan take a trip to investigate Serena’s boarding school - the one she went to before the first season of the show.
This episode really showcases the chemistry between Leighton Meester and Penn Badgley, and it’s easy to see why the writers decided to pair their characters up for a while.They are so fun together as very few other characters in the show can keep up withBlair and Dan’s wit. It also, of course, features flashbacks to Serena’s time at boarding school and finally answers some long-standing questions fans had about her.
It’s a great episode for exploring new character dynamics and deepening the history of the show.
5The Goodbye Gossip Girl
Season 2, Episode 25
When this episode first aired, it felt like the writers had been hedging their bets in case it became the show’s series finale.It’s graduation day for most of the characters, so there’s a lot of nostalgia and a lot of moments where it seems like they are fully moving on from their past lives.
Blair passes her crown on to Jenny (though that would not last in future seasons), Serena and Dan decide to remain friends, and Blair and Chuck confess their feelings for one another. Those all feel like the final moments of a show, but because this isGossip Girl, the series also throws in a huge zinger - making Serena angry enough at the anonymous blogger that she becomes determined to unmask Gossip Girl once and for all.
Thankfully, Serena does not succeed so that the audience can continue to speculate about Gossip Girl and indulge in all of the drama for another four seasons, but it is certainly fun to watch her try.
4G.G.
Season 5, Episode 13
The 100th episode of a television series is a huge landmark for a show. ForGossip Girl, it meant the writers decided to give fans a fun dream sequence that involves Blair as Audrey Hepburn and Serena as Marilyn Monroe in a musical sequence that sees Dan trying to choose between them. It’s an incredibly fun sequence that was not like anythingGossip Girlhad done previously. That alone makes the episode stand out.
The rest of the episode centers around Blair getting ready to marry an actual prince. While it seems like the fairy tale she always wanted, there is much more to it. Chuck still has feelings for her, Dan still has feelings for her, and Blair knows that something is not right.In true dramatic Blair fashion, she calls Dan for help at the end of the episode, kicking off the arc that would lead to their romance and giving the audience a dose of drama that would have larger ramifications for her relationships with Prince Louis, Chuck, and even Serena.
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Season 3, Episode 22
…a delicious season finale.
IfGossip Girlfans watch the show for the relationship drama, this is the episode for them. Serena ends up single after Gossip Girl blows up her love life again, Jenny ends up at odds with just about everyone, and Blair and Chuck seemingly end their relationship, though neither of them are really at fault for the end. Georgina also makes her return to the show.
All around, it is a delicious season finale.Gossip Girlalways knows how to end a season to keep the fans wanting to come back for the next.For fans who watched this one live, they would have been on tenterhooks waiting for season 4 to premiere because the final moments of the episode feature Chuck shot without anyone knowing about it. All of the relationships blowing up and Chuck at Death’s door make for the perfect way to end a season.
2Victor/Victrola
Season 1, Episode 7
This episode’s incredibly high ranking among the bestGossip Girlepisodes is two-fold.
On the one hand,this is a great early episode to explore family dynamics in the show. The audience gets to see why Chuck is the way he is when they see his interactions with his father. They also get a glimpse into Nate’s not-so-perfect homelife while his father is struggling with addiction.
On the other hand,this episode also marks the official start ofChuck and Blairas the show’s biggest will-they-won’t-they couple.While the show plays with romantic relationship dynamics among a lot of its main cast for the entire run of the show, Chuck and Blair always end up in one another’s orbit, and it starts here. Up until this point, Blair has been trying very hard to maintain a facade of perfection that includes her relationship with Nate, but she ends up sleeping with Chuck in the back of a limo.
If there is any episode of the show that demonstrates how the writers loved to employ story twists, it is this one.
1Blair Waldorf Must Pie
Season 1, Episode 9
It really solidifies that Serena and Blair are the core of the show…
“Blair Waldorf Must Pie” is the first Thanksgiving episode of the show. It’s the best holiday episode the show has. It’s also the best episode ofGossip Girl, and it happened very early in the show’s run.This episode digs into so many of the family dynamics in the show in a great way and also gives a lot of surprising background on the characters. The episode reveals Blair’s struggle with bulimia, Dan’s interest in Serena from an entire year prior to the events of the show, and the romantic history between Serena’s mother and Dan’s father.
It also gives some great insight into Blair’s need for perfection and her friendship with Serena.Though the two might be at one another’s throats a lot, Serena is the person Blair calls on Thanksgiving when she suffers a relapse with her eating disorder, and Serena immediately shows up and gets her out of the house. Serena and Blair do not hesitate to have Thanksgiving dinner at a diner with Eric, Jenny, and Dan. It really solidifies that Serena and Blair are the core of the show, even if it seems like romances take a front seat in later seasons.
“Blair Waldorf Must Pie” offers some of the best character work in the show, and that is what makes it even better than some of the more scandalous episodes ofGossip Girl.
Gossip Girl
Cast
Set among Manhattan’s elite, this drama series follows wealthy teenagers whose scandalous lives are exposed by an anonymous blogger. The show delves into themes of betrayal, ambition, and the complexities of high-society friendships, as the characters navigate interpersonal conflicts and personal aspirations.
