The 20 Best Episodes of Gossip Girl

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Gossip Girl is returning to HBO Max with a new reboot premiering July 8, featuring 10 juicy hour-long episodes featuring the original eponymous narrator Kristen Bell.

The reboot will take place eight years after the final surprising twist ending that revealed the true identity of Gossip Girl. We've been clued in on how stylish–and cool–the new characters are, but don't know too many details about the new reboot.

As we wait for the premiere, we're taking a look back on the six original seasons, in all its high-society New York glory. Here are the best episodes of Gossip Girl, to catch up on while you wait for the remake.

Leighton Meester as Blair Waldorf and Blake Lively as Serena Van Der Woodsen in season one of Gossip Girl.

GOSSIP GIRL, Emma DeMar, Nicole Fiscella, Amanda Setton, Dreama Walker, Taylor Momsen, Leighton Mees

Leighton Meester as Blair Waldorf and Blake Lively as Serena Van Der Woodsen in season one of Gossip Girl.
Photo: © CW Network / Courtesy Everett Collection

“The Pilot,” Season 1, Episode 1

Of course, the very first episode of Gossip Girl has to be on this list. It’s the introduction to all of the characters and their basic plotlines throughout the six seasons: Serena, who bites her lower lip and falls for guys within five minutes; Blair, who pretty much hates Serena but still acts like her best friend; Daniel/Lonely Boy (imagine that being your nickname, yikes), who’s creepy, stares longingly in the background, and is low-key miserable; Nate, who doesn’t really serve much of a purpose but is beautiful; Chuck, an odd 50-year-old in a 17-year-old body (he eventually does undergo a rebrand); and Jenny, who longs for nothing more than to be a Manhattan elite.

It also introduces us to the fact that these sophomores in high school attend parties on weekdays far more than anyone else does, and that their original casting for Eleanor Waldorf was abysmal.

“Victor/Victrola,” Season 1, Episode 7

The episode where Chuck and Blair's romance officially began. Bart Bass is interested in buying a burlesque club, so he sends his sophomore-in-highschool son to go check it out. While he's there, Blair gets over her breakup with Nate by letting it all go on the burlesque stage–and Chuck's into it. Then Blair is very into Chuck being into it. So into it that she loses her virginity to him in the back of his limo. Very different experiences from when I was a sophomore in high school but an episode to remember.

“Blair Waldorf Must Pie,” Season 1, Episode 9

Our introduction to the best of Gossip Girl: the Thanksgiving episodes. The introductory Thanksgiving episode has a little bit of everything: a glimpse at just how long Dan has been obsessed with his current girlfriend, Serena; flashbacks to happier times at the Waldorf family before Blair’s dad left her mom for a hot male model named Roman; the fact that Lily Van der Woodsen and Rufus Humphrey are basically the adult version of Dan/Serena and that they had a full-blown love story; and the fact that despite having a full spread of food on almost every table in this show, the characters never eat any of it.

“Desperately Seeking Serena,” Season 1, Episode 15

It's springtime in the Upper East Side which means it's time for us to all be introduced to the one and only Georgina Sparks. This episode really highlights what we all love about this show. It has amazing outfits and everyone's having cosmopolitans in bars on a school night even though they're supposed to be in what, the 10th grade?

Blair Waldorf sabotages Nelly Yuki before the SATs because she's Blair Waldorf. Nervous that Nelly will get a better score than her and take the only spot in Yale, Blair decides to ruin her chances of scoring well by playing the song that reminds Nelly of her ex-boyfriend – it's by Flo Rida – then making sure said boyfriend stops by to ruin Nelly emotionally, then taking out her batteries of her calculator before the SATs. Justice for Nelly Yuki even though she likes Flo Rida.

Blake Lively and Leighton Meester in Gossip Girl.

GOSSIP GIRL, Blake Lively, Leighton Meester, 'The Blair Bitch Project', (Season 1, ep. 113, aired Ap

Blake Lively and Leighton Meester in Gossip Girl.
Photo: © CW Network / Courtesy Everett Collection

“Never Been Marcused,” Season 2, Episode 2

Surprise! Blair Waldorf’s personality-less boyfriend is actually an English Lord. Surprise, part two! English Lord’s mom is the older, married woman that Nate is having an affair with. They met in book club, because that’s totally normal for high-school students and married women to be a part of one together.

Chuck decides to stir the pot and bring older woman/Marcus’s mom to a party as his date (again, not okay), and Kristen Bell/Gossip Girl sums up this episode and all of its absurd plotlines quite succinctly with her voiceover, questioning, “What’s this? Chuck’s date and Blair’s date are mother and son? And Nate and Blair are exes? And Nate and the mother are in a book club? Now there’s a novel plot twist.” Couldn’t have said it better myself, GG.

“New Haven Can Wait,” Season 2, Episode 8

Serena and Blair are fighting again! Except this time it's at Yale! Serena decides to go visit, accepting a personal invitation from the Dean of Yale himself. We see the two battle it out for attention at an exclusive invite-only event, only to kiss-and-make-up the next day. As always.

“Pret-a-Poor-J,” Season 2, Episode 8

This episode centers around Jenny basically calling out how unfair her unpaid internship to Eleanor Waldorf is, since she’s making most of the designs, befriending model/feminist Agnes, and going behind Lonely Boy/her brother’s back to hook up with Nate in one of his few age-appropriate relationships. So, in conclusion, we support Jenny and this episode.

“The Goodbye Gossip Girl,” Season 2, Episode 25

Everyone is graduating high school! S and B and D and N and C are all so excited to leave Constance Billard and Gossip Girl behind. But during their graduation ceremony, Gossip Girl lets everyone know that they can't really get rid of her that easily. S freaks out because she thought it would finally be the end of everyone knowing her business, so she decides to retaliate against the one and only GG. Gossip Girl decides to respond by sending out every single blast that anyone has ever sent to GG. Spicy.

Also, Chuck tells Blair he loves her for the first time in this episode. Rewatching the show and seeing how problematic Chuck Bass's character is, and how he's basically given a free pass to rebrand himself as a suitable guy for Blair Waldorf, it's not as cute. But it happened.

Taylor Momsen as Jenny Humphrey in Gossip Girl.

GOSSIP GIRL, foreground: Taylor Momsen, 'Pret-a-Poor-J', (Season 2, ep. 208, aired October 27, 2008)

Taylor Momsen as Jenny Humphrey in Gossip Girl.
Photo: © CW Network / Courtesy Everett Collection

“The Freshmen,” Season 3, Episode 2

We’ve made it to college. All the characters got into Ivy League schools last season, even though they are rarely seen doing schoolwork, but for show purposes, most of them decide to go to NYU. Blair Waldorf is no longer Queen B—no one at NYU cares about her headbands! Instead, they’re more interested in her roommate, Georgina, who’s back to wreak havoc. Vanessa becomes romantically involved with an awkward guy who ends up being—gasp!—Rufus and Lily’s secret love child. Finally, and most importantly, Blair and Chuck are really cute in this one.

“Dan de Fleurette,” Season 3, Episode 4

This episode has a lot of surprises. The introduction to Hillary Duff as a cast member in season three! Tyra Banks as an emotional actress who takes advice from Serena! And finally, Little J becoming the new Queen B of Constance Billard: reluctant at first, but then ending the episode by demanding her minions to “make sure a yogurt is waiting for her on the steps of the Met.”

“They Shoot Humphreys, Don't They?,” Season 3, Episode 9

Little J is power hungry! She's decided she doesn't only want to be Queen B of the school, but is setting her eyes on an entire borough: The Upper East Side. She pulls a page out of Blair Waldorf's playbook and orders her minions to confirm the hottest date to Cotillion on Jenny's behalf. But, Eric is over Jenny and her power trip so he decides to sabotage her date plans so that his own boyfriend can be her escort. When Jenny finds out, chaos ensues, and she decides to upstage everyone and their dates by showing up with the one and only Nate Archibald. Impressive.

“The Treasure of Serena Madre,” Season 3, Episode 11

Nothing says Thanksgiving like a chaotic, unhinged storyline on Gossip Girl. Or several.

Serena is having an affair with Nate's cousin, Tripp, who is also married. Also he's her boss. So they decide to spend the holiday apart. But then Lily runs into Tripp's wife, Maureen, on the street, and they're both wearing the same Red Valentino tweed jacket! So of course, Lily invites Maureen and Tripp to dinner with her family, and chaos ensues.

This episode comes to a climax at the Thanksgiving dinner table, when Lily finds out Serena is in fact in a relationship with a much older, married man, and Jason Derulo's “Whatcha Say” plays as everyone exits the table.

Hilary Duff in season 3 of Gossip Girl.

GOSSIP GIRL, Hilary Duff, 'Dan de Fleurette', (Season 3, ep. 304, aired October 5, 2009). 2007-. pho

Hilary Duff in season 3 of Gossip Girl.
Photo: © CW Network / Courtesy Everett Collection

“Double Identity,” Season 4, Episode 2

So much has happened in such a short amount of time. Chuck was shot and mugged in Paris and is now being taken care of by Fleur Delacour from Harry Potter and the Goblet of Fire. Dan thinks he has a baby with Georgina, Blair and Chuck reunite for a fleeting moment before she realizes she must let him go, and then Blair meets a member of the royal family of Monaco at a museum while staring at a painting. She then gives him one of her Roger Vivier heels to find her with. How can you not love this show?

“Juliet Doesn’t Live Here Anymore,” Season 4, Episode 8

In this episode, we come to learn that Nate’s new romantic interest, Juliet, is actually obsessed with taking down Serena, thanks to a very interesting backstory. She’s also the cousin of Serena’s professor/love interest, Colin (again with the not-okay-whatsoever relationships), and is lying about being rich and lives in a studio in an “unsafe neighborhood,” according to Vanessa, so it’s probably a really nice neighborhood in Manhattan. Before Juliet and Vanessa can expose Serena’s affair with her professor—which probably should have been exposed—Team Constance Billard defend Serena and kick Juliet out of Manhattan, because they own the city.

“The Townie,” Season 4, Episode 11

We're not in the Upper East Side anymore! Dan and Blair have left Manhattan and are trying to find out what really happened when Serena was in boarding school. This episode has it all: Dan and Blair being an (unlikely) amazing duo, flashbacks to Serena's wild past in boarding school, a glimpse into why Juliet actually hated Serena, and answers to all the questions we've had in the past few episodes.

<h1 class="title">GOSSIP GIRL, (from left): Blake Lively, Leighton Meester, 'Double Identity', (Season 4, ep. 402, air</h1><cite class="credit">Photo: © CW Network / Courtesy Everett Collection</cite>

GOSSIP GIRL, (from left): Blake Lively, Leighton Meester, 'Double Identity', (Season 4, ep. 402, air

Photo: © CW Network / Courtesy Everett Collection

“Yes, then Zero,” Season 5, Episode 1

Upper East Side meets 90210. In this juicy episode, Serena is interning on a movie set: a full-blown working gal. Nate and Chuck come to visit her on set, where Chuck explains he has a new philosophy on life, which involves him saying “yes” to everything. (Inspiring.) Nate pretty much does nothing in this episode but look beautiful, as usual, until he meets a very hot older woman (how did they get Elizabeth Hurley on this show?) and suddenly has a purpose again. And 19-year-old Blair has her wedding dress fitting with Prince Louis, where another bombshell drops: She’s pregnant. Again, how could you not love this show?

“Rhodes to Perdition,” Season 5, Episode 9

In this episode, Serena is into Max, who’s Serena’s cousin Charlie’s ex-boyfriend. They’ve all gathered together to celebrate their dear old grandmother Cece at a fabulous Studio 54 party, where Fake Cousin Charlie is trying to get her trust fund money from Cece to share with her fake mom, Carol, Serena’s aunt. Max exposes the entire lie, explaining that Charlie is in fact a broke actress named Ivy, but CeCe defends her, saying, “I know in my bones that this is my granddaughter,” who up until a few months ago, she’d never met, even though she’s the same age as Serena. The episode ends with Fake Charlie/Ivy securing her status as a Rhodes, and saying bye-bye to one of the only somewhat honest characters on this show, Max, explaining, “I’m a Rhodes now.” Delicious!

“Crazy, Cupid, Love,” Season 5, Episode 15

It's Valentine's Day in the Upper East Side! You know what that means. A high-school themed party.

Nate throws a party and decides to hire his new friend/love-interest's catering company. His new friend is Lola, who is actually Serena's real cousin who Fake Cousin Charlie is trying to impersonate. Blair tries to get Serena and Dan back together, but turns out that Dan actually just wants Blair and decides to kiss her instead. Georgina records the whole thing and Serena is in shock and betrayed. Basically the same plotline from every season before that involves Blair, Serena, and someone else.

Chace Crawford, Blake Lively, and Ed Westwick in Gossip Girl.

GOSSIP GIRL, (from left): Chace Crawford, Blake Lively, Ed Westwick, 'Yes, Then Zero', (Season 5, ep

Chace Crawford, Blake Lively, and Ed Westwick in Gossip Girl.
Photo: © CW Network / Courtesy Everett Collection

“Dirty Rotten Scandals,” Season 6, Episode 3

So much has happened since season five. Serena is dating Matt from 7th Heaven. His daughter, who is in high school, is dating Nate (again, why was this okay?), and is basically a mini Queen B. Fake Cousin Charlie/Ivy is now dating Rufus, and the iconic Nelly Yuki returns as a Women’s Wear Daily editor who trashes Blair’s fashion show, which Blair blames on Serena because, as everyone knows, Blair hates Serena. As usual, Dorota and Chuck and Blair’s relationship are the highlights of this episode, and it ends on a high note, with Dorota giving Blair some words of wisdom and strength: “You will make Miss Eleanor proud.”

“New York, I Love You,” Season 6, Episode 10

Bart Bass (who died in a previous season but is revealed to be very much alive) actually dies after trying to attack Chuck. Then we find out that Lonely Boy is Gossip Girl (possibly the most disappointing ending of a show until season eight of Game of Thrones), and Serena backs him up because all Serena cares about is the fact that he’s obsessed with her. Chuck and Blair get married in Central Park, and the episode ends with a flash-forward several years to their cute son, and the whole crew getting ready for Serena and Dan’s wedding in an apartment. The ending cuts to a montage of Gossip Girl saying she will always be around, and that the constant need for gossip is what keeps her going.

Originally Appeared on Vogue