When dissecting the most detestable characters on “Gossip Girl,” we dive into a world crafted by Josh Schwartz and Stephanie Savage, loosely based on Cecily von Ziegesar’s novels. This iconic series offers a dramatic, campy portrayal of immensely privileged teens and young adults navigating New York City’s elite Upper East Side with unmatched authority. The show’s allure lies in its characters—each one a master of deceit and manipulation, with a hint of wickedness. The HBO Max reboot, which aired from 2021 to 2023, missed the mark by trying to paint these characters as sympathetic. From the sharp-tongued Blair Waldorf (Leighton Meester) to her socialite best friend Serena van der Woodsen (Blake Lively), and from the golden boy Nate Archibald (Chace Crawford) to the rebellious Chuck Bass (Ed Westwick), this depiction of New York is rife with characters consistently engaged in terrible acts against one another. So, how do we define a “bad” character in such a setting?

Surprisingly, the gravest sin a “Gossip Girl” character can commit isn’t trading a partner for a hotel, betraying a best friend, or leaking secrets to the notorious blogger. The ultimate transgression is being dull, irritating, or worst of all, both. Yet, there remains a character who, despite being neither boring nor annoying, commits such heinous acts that they top the list of the worst. With that in mind, here are the five most reprehensible “Gossip Girl” characters—spoiler alert!

Vanessa Abrams, played by Jessica Szohr, proclaims disdain for the wealthy, spoiled progeny of New York’s Upper East Side elite, yet she spends an excessive amount of time amidst them. Introduced in Season 1 as a supposed romantic rival to Serena while she dates Dan, Vanessa’s role as a true competitor is laughable given Dan’s infatuation with Serena. Despite Szohr’s commendable efforts, Vanessa comes across as insufferably self-righteous in a series that thrives on scheming and deception. She perceives herself as morally superior, yet consistently meddles in others’ affairs with disastrous results.

For someone who claims that she hates the wealthy, spoiled, and privileged offspring of New York’s elite who reside on the Upper East Side, Jessica Szohr’s Vanessa Abrams sure does spend a frankly inordinate amount of time around those same wealthy, spoiled, and privileged kids. Introduced partway through Season 1 as an ostensible romantic rival for Serena while the “it girl” is happily dating Dan — though to call Vanessa a true romantic rival is ridiculous, considering that Dan is head over heels in love with Serena — Vanessa, put simply, stinks. With all due respect to Szohr, who does the absolute best she can with the material she’s given by the series, Vanessa is a dull person who genuinely thinks she’s better than every other character on the show but is constantly getting in the way, doing boneheaded things, and being incredibly self-righteous on a show where the best thing a character can do is connive and scheme.

Almost any plotline involving Vanessa is a dud — her weird fling with Chuck Bass in Season 2 is one of the most bizarre things this show ever did, which is really saying something — and whenever she gets involved with anyone else’s plotline, like Blair’s doomed romance with Lord Marcus Beaton (Patrick Heusinger) or Dan’s brief relationship with movie star Olivia Burke (Hilary Duff), she ruins that too. Thankfully, after the close of Season 4, Vanessa stopped appearing as a series regular, though she did make a small cameo in the show’s series finale during its sixth and final season.

When we first meet Katie Cassidy’s Juliet Sharp in season 4 of “Gossip Girl,” she’s introduced as a mysterious girl reading a book alone at a restaurant who catches Nate Archibald’s eye. As it turns out, Juliet has a much more sinister mission than just scoring a date with Nate; she’s got a long-standing connection to Serena van der Woodsen and is only in New York to bring her down. Why? Well, Juliet’s brother, Ben Donovan (David Call) is in prison thanks to Serena’s mother Lily van der Woodsen, who forged Serena’s signature on a document credibly accusing Ben of statutory rape due to an alleged relationship he had with Serena while she was a student at boarding school and Ben was her teacher. One problem? Nothing ever happened between Ben and Serena while she was underage — despite her best efforts, Ben actually turned down her advances — but that doesn’t matter to Juliet, who wants to ruin Serena’s life in return for Ben’s wrongful incarceration.

The way Juliet goes about this is truly insane, even by “Gossip Girl” standards. Not only does she spread vile rumors about Serena having a sexually transmitted disease, she eventually impersonates Serena at a party, drugs her drink, and gaslights Serena into believing she went on a dangerous bender — which eventually sends Serena to a rehab facility despite the fact that Juliet attacked her. The only good thing that Juliet ever brings to “Gossip Girl” is a scene where the main gang surrounds her and runs her out of town in Season 4 while they’re all in evening wear, which is incredibly campy and incredibly fun.

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN’s National Helpline at 1-800-656-HOPE (4673).

It’s mean to say that, during his tenure on “Gossip Girl” as Dr. William van der Woodsen, William Baldwin is doing a sub-par impression of his brother Alec’s “30 Rock” character Jack Donaghy … but unfortunately for this less-famous Baldwin, it’s also true. (In the sixth season, he tells a character we’ll discuss momentarily that she should go back to Florida and be “queen of the swamp people,” and it definitely sounds like a Jack line that “30 Rock” creator Tina Fey left on the cutting room floor for being too stupid.) Anyway, William is Serena’s estranged father and Lily’s ex-husband, and in the third season of the show, he re-enters the chat after Serena keeps trying to get in touch with him and mend their relationship. Besides his weird, growly way of talking, though, William is evil, and not even in a fun or interesting way.

By the time William finds himself back with his ex-wife and two children — Serena’s younger brother Eric, played by Connor Paolo, is much more hesitant about letting their dad back into their lives — Lily is already remarried to her longtime love Rufus Humphrey (Matthew Settle), something William does his best to ruin despite the fact that he and Lily have been apart for decades. Not only that, but in his capacity as a doctor, William starts prescribing Lily medication for a mystery illness that turns out to be caused by the very medication he’s supplying, so as if William isn’t bad enough, he also tries to win his wife back using Munchausen’s by proxy. The worst part, though?! This all works, and in the series finale, we see that Lily and William are married again (Rufus, for some reason, is married to singer-songwriter Lisa Loeb, who appears as herself).

The Florida woman in question who’s on the receiving end of William van der Woodsen’s “queen of the swamp people” dig is Ivy Dickens, a truly bizarre and wholly irritating “Gossip Girl” character played by Kaylee DeFer. When we first meet Ivy in Season 4 of the series, though, she’s going by Charlotte “Charlie” Rhodes, pretending to be the daughter of Lily’s sister Carol Rhodes (Sheila Kelley), the granddaughter of Lily’s mother CeCe Rhodes (Caroline Lagerfelt), and cousin to Serena. The reason for this ruse is that Ivy is an actress hired by Carol so that Carol can access the protected trust fund of her real daughter, the actual Charlie, without her knowledge (that Charlie, who also pops up in the series later on and goes by Lola, is played by Ella Rae Peck). 

Ivy wouldn’t be such an irritating character on “Gossip Girl” if she just appeared as a part of Carol’s scheme, but for some reason, the show keeps bringing her back into the fray over and over again, even writing a truly absurd plotline where the wealthy CeCe leaves her entire fortune to Ivy instead of her own daughter. Between that and Ivy’s romantic dalliances with everyone from Rufus Humphrey to William van der Woodsen to Nate to Dan Humphrey (Penn Badgley), she’s just unbelievably annoying on screen, which isn’t DeFer’s fault; it’s the writing. Pretty much every storyline the writers hand Ivy is a dud, and that’s why whenever she’s on-screen, even the most ardent “Gossip Girl” fan can’t help but let out a massive groan.

Without a doubt, the worst character on “Gossip Girl” is Dan Humphrey — because he’s Gossip Girl. Yes, in a reveal during the series finale “New York I Love You XOXO,” we learn that, this entire time, Dan has been spreading mean information and sharing secrets of the people closest to him, including his dad, his younger sister Jenny (Taylor Momsen), and literally all of his romantic partners. This makes some scenes in the early seasons of the show particularly goofy, though, because Dan spends a truly bizarre amount of time reacting to various Gossip Girl information blasts by himself and looking surprised, even though he’s ostensibly the one who wrote the posts; this can be explained by the fact that Internet sleuths guessed that Eric might be Gossip Girl and Josh Schwartz, who was originally planning on that exact reveal, decided to change course. Nate was also floated as a potential Gossip Girl — as Schwartz told Vulture after the show concluded, they went with Dan for a reason. “But in the end, it had to be Dan, because Dan’s a writer, observer, and could write in different styles,” he reasoned.

Not only is this stupid, but the ramifications of Dan being Gossip Girl are horrifying, especially when it comes to Serena, the ostensible love of Dan’s life. Despite spending years wooing her and ultimately marrying her, Dan spent a wildly long time cyber-bullying her in unbelievably vile ways, making him the show’s worst villain by far. Also, Dan is just smug and annoying, so that doesn’t help (with all due respect to Penn Badgley, who followed “Gossip Girl” by starring on “You,” a show that’s basically about Dan if he was also a murderer). “Bad” characters on “Gossip Girl” can be so fun, but Dan just … sucks.

“Gossip Girl” is streaming on HBO Max and Netflix now.