Gossip Girl kept mostly the same group of main characters throughout its entire run. Serena, Blair, Dan, Nate, and Chuck all remained in the Upper East Side spotlight, even as characters like Jenny and Vanessa went away. The show thrived on shock and scandal, which followed these five characters everywhere they went.
Out of all the drama, it's tough to choose just one scene for each character and named it the most iconic. Some characters - Serena, Blair, Dan - have plenty of defining moments in the show. Others, like Nate and Vanessa, are a tad harder to pin down. The show gave audiences enough juicy moments, though, and plenty of material to choose from and enjoy.
Georgina Is Back
Introduced at the end of season 1, Georgina Sparks is arguably the series' best antagonist. She's a cunning and cynical young woman who causes trouble simply because she loves chaos. Blair deals with her in the season 1 finale, but she returns in season 2, seemingly reformed after finding religion.
It's not long before Georgina is back to her old ways, though. During her most memorable scene, she calls Blair to let her know, memorably saying, "You can tell Jesus that the b**ch is back." The moment is prime soapy drama, enhanced by Michelle Trachtenberg's perfect delivery.
Vanessa Steals Dan's Novel
Vanessa goes through a chaotic journey during her time in the show. She starts as an outsider before slowly making her way in thanks to her relationships with Dan, Nate, and even Chuck. However, she soon becomes as scheming as all the others but still pretends like she's above them.
By the end of her story, she's burned all her bridges, and no one wants her in their life, not even Dan. After discovering his novel, Inside, and learning he doesn't want to publish it for fear of alienating Serena and company, Vanessa steals it and takes it to a publisher. It's a truly shameless action and the perfect sendoff to such a selfish character.
Jenny Presents Her Collection
Season 2 is a wild ride for Jenny. She works for Elanor Waldorf before quitting abruptly, befriends and is then betrayed by the chaotic Agnes Andrews, briefly gets together with Nate before he goes back to Vanessa, and ends the whole thing by becoming the new Queen of the Upper East Side.
In the midst of it all, she finds the time to create her first fashion collection, which she debuts during an event honoring Bart and Lily. The collection itself is quite ugly, but the fact that a sixteen-year-old pulled such a boss move is impressive.
Rufus Confesses To Lily
Back in season 1, Rufus and Lily engage in a will-they-won't-they dance that's very entertaining to watch. They can't get together because obstacles keep getting in their way, like Rufus' soon-to-be ex-wife Allison, or Lily's soon-to-be future husband, Bart.
During the Cotillion episode, Rufus learns the truth about why Lily broke up with him in the past. He calls her, and the two have an honest and heartfelt conversation about what could've been. He ends the call by revealing he regrets allowing her to let him go, leaving her speechless.
Lily Has Her Sister Arrested
In the pantheon of bad mothers, Lily Van der Woodsen has a place of honor. The show reveals she was an absent parent during her children's infancies, and she isn't much better during her time in the show. Lily constantly goes behind her family's back and keeps secrets from them, frames a man and sends him to prison, and is an overall untrustworthy person.
When Lily learns that her sister, Carol, slept with her ex-husband, William and that her daughter, Lola, is his, she loses what little patience she has left. She calls the cops and has Carol arrested while having dinner with a reporter. Carol sure had it coming, especially after the whole Ivy debacle, but even for Lily, that was stone cold.
Nate Confronts His Father
Like Lily, Howard "the Captain" Archibald isn't exactly father of the year. In season 1, he blames Nate when his wife discovers his marijuana.
Nate finally confronts his father in the street, and the Captain loses control. He punches Nate in the face and quickly understands the gravity of his situation. Nate does too and allows the cops to take his father, sadly walking away from the scene. It's a tough scene to watch, particularly because Nate's pain is real. Fortunately for these two, the Captain sobers up and becomes a better father after his stint in jail.
Blair & Chuck Meet In Paris
Because their relationship is so consuming, Blair and Chuck can't exist as separate, independent entities in the show. This is ultimately detrimental to both characters, who need each other to survive and lose their individualities in the process. Blair and Chuck, however, are instrumental to Gossip Girl's success, and their turbulent affair provides most of the series' most memorable moments.
Their most iconic happens at the start of season 4. After their break-up in the season 3 finale, Chuck and Blair have a climactic encounter in a Parisian train station. They share an intimate and honest moment where they confess they need each other but can't be together. Both allow themselves to be vulnerable and open, a rarity for the characters. In the end, they reach a feeble understanding, and it's refreshing to see them expressing their feelings in a healthy way instead of retorting to the twisted games they both enjoy.
Dan is Gossip Girl
For better or for worse, Dan was Gossip Girl. The choice made no sense, and multiple plot holes contradict the reveal. However, the fact remains that he's still Gossip Girl, and there's nothing fans can do about it.
His identity doesn't come to light until the last episode, and the show treats it like some shocking, game-changing reveal. In truth, Dan as Gossip Girl left a bitter aftertaste for fans and came off as more than a tad contrived. Over the years, fans became more comfortable calling out Dan's problematic behavior. In the end, love it or hate it, there's no denying that this twist remains Dan's most unforgettable moment in the show.
The Return Of Queen S
During the show's first two seasons, Serena is the show's de-facto protagonist. She becomes more of a supporting player to Blair and Chuck's storyline in later seasons, but at the beginning, it's all about her. In season 2, and after her second break-up with Dan, the two try to be friends, but things end badly when he starts dating another girl.
Serena becomes jealous, and her minions pull a stunt on the girl. Dan confronts Serena and doesn't believe her when she says it wasn't her. Angry and hurt, Serena decides to live up to her reputation. She walks into Constance like the new Queen, cruel, ice-cold, and beautiful. The crowd parts like the Red Sea, and Dan watches in awe and fear at the new and improved Queen Serena.