The Best Episodes of Gossip Girl

Last Updated: May 30, 2019

Privileged teens living on the Upper East Side of New York can hide no secret from the ruthless blogger who is always watching.

New York, I Love You XOXO

#1 - New York, I Love You XOXO

Season 6 - Episode 10

In a fashionable farewell to remember, our favorite Upper East Siders join forces for one last soiree, and the shocking identity of Gossip Girl is finally revealed.

star 8.46
457 votes
Directors: Mark Piznarski
Writers: Stephanie Savage
Buy on iTunes
The Goodbye Gossip Girl

#2 - The Goodbye Gossip Girl

Season 2 - Episode 25

Gossip Girl decides to liven things up at the Constance Billard and St. Jude’s graduation by sending out a shocking and damaging email blast in the midst of the commencement ceremony, stirring Serena to come up with a plan of attack. The Mean Girls challenge Jenny to throw her hat in the ring to succeed Blair as Queen Bee next year. Lily and Rufus struggle to repair their relationship after Lily’s betrayal. As for the cliffhangers, Blair and Chuck finally… and Serena is shocked by… and Georgina decides to… and Dan, Nate, and Vanessa unknowingly…. Jenny and Eric do something they might end up regretting.

star 8.45
285 votes
Directors: Norman Buckley
Writers: Joshua Safran
Watch on Amazon Buy on iTunes

#3 - G.G.

Season 5 - Episode 13

The much-anticipated 100th episode will open with a musical dream sequence featuring Serena, Blair and all the men in their lives. Also, while Chuck wrestles with the reality that Blair is about to walk down the aisle with Prince Louis, the return of Georgina Sparks might make the royal affair a royal disaster.

star 8.24
308 votes
Directors: Mark Piznarski
Writers: Joshua Safran
Buy on iTunes
The Townie

#4 - The Townie

Season 4 - Episode 11

Blair and Dan decide to team up to take down an MIA Juliet. The odd couple takes a road trip to Cornwell, where they find Damien Daalgard. He gives Blair and Dan some missing pieces to find out why Juliet is after Serena. Meanwhile, Juliet finds out about Blair and Dan's present in her home town and decides to return to New York to finish what she started. Lily is keeping a secret from Chuck, which Rufus finds out. Nate tells his mother about what the Captain has been up to and she decides to get through with the divorce. When Nate realizes he had it all wrong a last attempt to rescue his parent's marriage fails due to Anne's longing to the rich society of Manhattan.

star 8.19
247 votes
Directors: Joe Lazarov
Writers: Stephanie Savage, Amanda Lasher
Watch on Amazon Buy on iTunes
Victor (Victrola)

#5 - Victor (Victrola)

Season 1 - Episode 7

Serena and Dan finally accept that they are crazy about each other, despite that they come from polar opposite worlds. Chuck thinks of investing in a club trying to make his father Bart Bass proud of him. Nate confronts his father, about the drugs he found in his house but he denies having a problem. Jenny discovers a secret that her parents have been keeping from her. Finally, Blair is devastated by Nate's actions when Jenny reveals that Nate kissed her by accident thinking she was Serena.

star 8.17
379 votes
Directors: Tony Wharmby
Writers: K.J. Steinberg
Watch on Amazon Buy on iTunes
They Shoot Humphreys, Don't They?

#6 - They Shoot Humphreys, Don't They?

Season 3 - Episode 9

Not satisfied with just being Queen of Constance Billard, Jenny sets her sights on becoming the Queen of all the Upper East Side by landing the hottest escort for Cotillion. Meanwhile Dan and Vanessa try to convince Olivia to stay in NY by showing her the "true college experience."

star 8.17
257 votes
Directors: Alison Maclean
Writers: Amanda Lasher
Watch on Amazon Buy on iTunes
All About My Brother

#7 - All About My Brother

Season 1 - Episode 16

Georgina informs Serena that she can reveal a deep dark secret from Serena's past, but no one is prepared for what Georgina does next. Blair and Jenny's power struggle continues when each of them start spreading scandalous rumors about each other on Gossip Girl. Dan sees Jenny's new beau, Asher, cheating on her, but Jenny won't listen to him. Rufus goes to Lily for advice on how to handle Jenny's new behavior. Serena tries to confront Georgina, but she leaves before Serena has a chance. After this, Serena says that she and Georgina are not friends.

star 8.17
336 votes
Writers: Paul Sciarrotta
Watch on Amazon Buy on iTunes
Hi, Society

#8 - Hi, Society

Season 1 - Episode 10

Serena's grandmother announces that Serena has to go to Debutante Ball. However, Dan is not what CeCe wants as an escort for Serena, and she makes her opinion heard loud and clear, causing a rift between Serena and Dan. Although they are officially broken up, Nate asks Blair to go to the ball with him. A jealous Nate begins to suspect that Blair is seeing someone else. Jenny finds herself having to make the decision of either attending her mother's art opening or following her dreams to the Debutante Ball, even though her parents don't want her to go.

star 8.15
347 votes
Directors: Patrick Norris
Writers: Joshua Safran
Watch on Amazon Buy on iTunes
The Blair Bitch Project

#9 - The Blair Bitch Project

Season 1 - Episode 14

Having been recently dethroned as Queen Bee, Blair returns to school with the support of Serena to find she is still on the outs with her old friends. Dan visits his mother over spring break, and when he returns, Jenny is on the verge of becoming a full-fledged member of the A-List crowd. Jenny must go to dangerous and even illegal lengths to fit in. Serena struggles to adjust to living with Chuck, and receives disturbing packages from an unknown sender.

star 8.14
338 votes
Directors: J. Miller Tobin
Writers: K.J. Steinberg
Watch on Amazon Buy on iTunes
There Might be Blood

#10 - There Might be Blood

Season 2 - Episode 9

Serena invites Aaron to a charity event, but soon uncovers a secret Aaron has been keeping from her. Thinking it will help her get into Yale, Blair agrees to babysit the 15-year-old daughter of a Yale donor, but her plan quickly backfires. Meanwhile, Jenny and Agnes plan a fashion show.

star 8.12
277 votes
Directors: Michael Fields
Writers: Etan Frankel, John Stephens
Watch on Amazon Buy on iTunes
The Revengers

#11 - The Revengers

Season 6 - Episode 9

After a run-in with an increasingly paranoid Bart, Blair grows alarmingly concerned for Chuck’s safety. However, feeling confident that his father will never hurt him, Chuck makes a deal that could change his life. Wanting to make things better for Chuck, Blair devises a plan with the help of Serena, Georgina and Sage to try and get what they need out of Bart. Meanwhile, Nate's financial dilemma finally lands him in a place that he never thought he would be.

star 8.11
325 votes
Directors: Patrick Norris
Writers: Sara Goodman, Natalie Krinsky
Watch on Amazon Buy on iTunes
Raiders of the Lost Art

#12 - Raiders of the Lost Art

Season 5 - Episode 22

Chuck, Nate, Blair, Serena and Lola team up to uncover what they think is an explosive secret between Diana and Jack. Meanwhile, Dan is offered a prestigious fellowship in Rome for the summer.

star 8.10
287 votes
Directors: Bart Wenrich
Writers: Jake Coburn
Watch on Amazon Buy on iTunes
Last Tango, Then Paris

#13 - Last Tango, Then Paris

Season 3 - Episode 22

Blair must decide whether to meet Chuck at the top of the Empire State Building or risk losing their future together. A Gossip Girl gossip bomb involving Dan explodes Serena and Nate's relationship. Dorota and Vanya welcome their baby. Jenny hits rock bottom. Georgina returns to the Upper East Side... and she has an agenda.

star 8.10
248 votes
Directors: J. Miller Tobin
Writers: Joshua Safran, Stephanie Savage
Watch on Amazon Buy on iTunes
Double Identity

#14 - Double Identity

Season 4 - Episode 2

Living out a real-life fairytale in Paris, Blair is pursued by a handsome young man, Louis, who she suspects is a member of Monaco's royal family. A very concerned Lily asks Serena to help her find Chuck, who hasn't been heard from or seen in months. Meanwhile, Chuck Bass is as we've never seen him before, adjusting to a fresh start in Paris with a mysterious new woman, Eva, at his side. Juliet offers to help Nate win Serena back, suggesting that reigniting Dan and Vanessa's romance may just be the trick to remove Dan from the Dan-Serena-Nate love triangle.

star 8.10
278 votes
Directors: Mark Piznarski
Writers: Joshua Safran, Sara Goodman
Watch on Amazon Buy on iTunes
School Lies

#15 - School Lies

Season 1 - Episode 12

Serena, Blair, Nate, Chuck and their class break into the school swimming pool for a night of fun, but when someone nearly dies, the school threatens to expel the person responsible for the break-in. Everyone agrees to not say anything, but this creates major problems between Serena and Dan. Vanessa, while working on a documentary project about private schools, accidentally captures Blair and Chuck discussing their affair. Lily tries to tell Rufus how she really feels about him.

star 8.09
339 votes
Directors: Tony Wharmby
Writers: Lenn K. Rosenfeld
Buy on iTunes
Memoirs of an Invisible Dan

#16 - Memoirs of an Invisible Dan

Season 5 - Episode 4

After much deliberation, Dan decides to gather Serena, Blair, Nate, Chuck, Rufus and Lily to reveal the truth about his book in the hope that they will support him at his book party. Meanwhile, Blair and Louis hit a crises point after Louis reads Dan's book. Diana learns incriminating information about one of Nate's friends and uses it to her advantage.

star 8.08
277 votes
Directors: Tate Donovan
Writers: Amy B. Harris
Watch on Amazon Buy on iTunes
Summer, Kind of Wonderful

#17 - Summer, Kind of Wonderful

Season 2 - Episode 1

As the summer draws to a close in the Hamptons, Serena and Nate have everyone fooled into thinking they are a couple to cover up the fact that Nate has been hooking up with a married, older woman. Blair returns from abroad with a hot guy on her arm making a very jealous Chuck question his decision to leave Blair stranded at the heliport. Dan has spent the summer assisting a famous author. While interning for Eleanor Waldorf's company, Jenny sneaks an invite to a much-coveted Hamptons' White Party at which Eric introduces her to socialite Tinsley Mortimer.

star 8.07
354 votes
Directors: J. Miller Tobin
Writers: Joshua Safran
Watch on Amazon Buy on iTunes
The Thin Line Between Chuck and Nate

#18 - The Thin Line Between Chuck and Nate

Season 1 - Episode 13

Gossip Girl reports that Serena van der Woodsen was seen buying pregnancy tests. Of course, on the Upper East Side, the truth is often even juicier and more scandalous than the gossip. Nate finds out about Blair and Chuck's affair. Everyone else also finds out what happened and Blair's life comes crashing down. Dan struggles to tell Serena those three words.

star 8.05
340 votes
Directors: Norman Buckley
Writers: Felicia D. Henderson
Watch on Amazon Buy on iTunes
The Serena Also Rises

#19 - The Serena Also Rises

Season 2 - Episode 5

In the midst of Fashion Week, a furious Blair learns that her mother, Eleanor, at the suggestion of her protege Jenny, has given Serena and her new socialite friend, Poppy Lifton, front row seats to the Eleanor Waldorf show. Hurt once again by Serena's popularity and her mother's betrayal, Blair decides to sabotage the show. Meanwhile, Dan starts hanging out with Chuck, but a walk on the dark side always has its risks and Dan learns that the hard way. Lily learns a secret that her new husband, Bart, has been keeping from her.

star 8.04
294 votes
Directors: Patrick Norris
Writers: Jessica Queller
Watch on Amazon Buy on iTunes
Woman on the Verge

#20 - Woman on the Verge

Season 1 - Episode 17

After Georgina reveals the true reason Serena left Manhattan, Serena goes back into her old habits. Her friends Blair, Nate, and Chuck, in order to help her, have to put their differences aside. Meanwhile, Rufus is excited when his band is invited to perform at a Rolling Stone-sponsored concert, but Lily is the last person on earth he expects to see at the performance, especially since her wedding rehearsal dinner is the same night.

star 8.04
327 votes
Directors: Tony Wharmby
Writers: Joshua Safran
Watch on Amazon Buy on iTunes
Shattered Bass

#21 - Shattered Bass

Season 4 - Episode 21

Charlie is finally starting to feel less like a fish-out-of-water with Serena and her friends, but complications present themselves when Charlie is invited to attend the Constance Billard alumni fundraiser. On the road to "happily ever after" Blair finds herself torn between the men in her life. Jack Bass return to the Upper East Side sets off a chain of events that could end up destroying Chuck and those closest to him.

star 8.02
234 votes
Writers: Sara Goodman
Watch on Amazon Buy on iTunes
Roman Holiday

#22 - Roman Holiday

Season 1 - Episode 11

Blair's father, Harold, comes home for the holidays with an unexpected guest. Blair cannot hide her disappointment and makes a plan to get rid of Roman forever. Jenny and Vanessa help Serena get the best Christmas present ever for Dan, who has a surprise of his own for Serena. Rufus refuses to remain the understanding husband any longer after Alison's former lover sends a letter to the house.

star 8.02
349 votes
Directors: Michael Fields
Writers: Jessica Queller
Watch on Amazon Buy on iTunes
The Wrong Goodbye

#23 - The Wrong Goodbye

Season 4 - Episode 22

The episode continues from the early events of the Constance Alumni event. Georgina Sparks turns up at the event looking for trouble. Serena and Vanessa reluctantly join forces to find Dan and Charlie, who does not take Dan's rejection of her well. Blair must make a choice between the men in her life when her life is in danger from Russell.

star 8.02
251 votes
Writers: Joshua Safran
Watch on Amazon Buy on iTunes
Rufus Getting Married

#24 - Rufus Getting Married

Season 3 - Episode 5

Lily and Rufus decide to move up their wedding to the next day, but will someone or something come between them before they become man and wife? Chuck discovers a secret that Carter has been keeping from Serena. Dan and Vanessa are pulled into one of Georgina’s schemes. Blair is suspect of Bree and shares her concerns with Nate.

star 8.02
272 votes
Directors: Ron Fortunato
Writers: Leila Gerstein
Watch on Amazon Buy on iTunes
Bad News Blair

#25 - Bad News Blair

Season 1 - Episode 4

Blair gets excited when her mother, Eleanor, chooses her to be the new face of her clothing line. However, Blair's happiness turns quickly into feelings of betrayal and jealousy when Serena takes her spotlight and Blair finds herself back in Serena's shadow. Meanwhile, Serena and Dan remember once again that they come from two very different worlds. Also, Nate and Chuck do a boys weekend to blow off steam after Ivy Week ends.

star 8.01
413 votes
Writers: Joshua Safran
Watch on Amazon Buy on iTunes