Summary
- Jenny Humphrey lost herself in her quest for popularity and became one of the most hated characters in Gossip Girl.
- Vanessa Abrams failed to live up to her potential as a relatable voice against wealth and privilege, coming off as a hypocrite.
- Lily van der Woodsen and Vanessa were both hypocritical characters who gave advice they didn't follow, making them unlikeable.
While Blair Waldorf, Chuck Bass, and their crew of wealthy friends aren't exactly the most likable people, some of the worst Gossip Girl characters are the supporting ones. Based on the Cecily von Ziegesar book series of the same name, Gossip Girl centers around a group of privileged teens in New York City's Upper East Side whose personal lives are reported on and skewered by the eponymous, anonymous blogger. The show ran for six seasons from 2007 to 2012 and inspired a short-lived Gossip Girl reboot series that debuted on Max (then known as HBO Max) in 2021.
Gossip Girl made huge stars out of its main cast, particularly Blake Lively (who played Serena van der Woodsen) and Penn Badgley (Dan Humphrey). But the teen drama also provided many opportunities for guest actors to make their mark, whether they played school rivals or love interests of the lead characters. Some actors even had guest roles on Gossip Girl before they were famous, like Sebastian Stan (Carter Baizen) and Rachel Brosnahan (a nameless "Girl"). Unfortunately, not every supporting player was embraced by the fanbase, and many unwittingly vied for the title of most hated character in Gossip Girl.
12 Jenny Humphrey
A lot of people did not like Little J, even though she came from the nicest and most normal family on the show. She really wanted to fit in at school and rise up from Brooklyn to the queen of Constance. To achieve this, she lost herself a bit and did not seem to care that she was hurting her loved ones and hurting herself. She stole, lied, cut class, picked up mean girl behavior and totally shut out the people who already liked the original and old Jenny.
The trouble with Jenny's descent into attempted villainy is that it wasn't gradual. It's like she was two different people — sweet little J and vicious backstabber. Jenny also attempted to usurp Blair's position of power, and the audience loved Blair Waldorf as Queen B. When Taylor Momsen decided to leave the show, The most humbling exit in Gossip Girl history, Jenny was literally banished from Manhattan by Blair — who was perhaps speaking for the audience.
11 Vanessa Abrams
Another character who was seemingly supposed to be likable but wasn't at all was Vanessa Abrams. She was a childhood friend of Dan’s, and she claimed to dislike the Upper East Side, though she never seemed to leave it. She even dated Nate Archibald, one of the richest people in the neighborhood. Gossip Girl had a great opportunity to comment on wealth and privilege through Vanessa and have her be the voice of the audience, but she just came across as a hypocrite.
Vanessa also dated Dan, and though audiences usually root for the childhood crush to win the object of their affection, Vanessa just didn't have the same chemistry with Dan that he had with Serena. And compared to Serena, and especially Blair, Vanessa's storylines just didn't have the same bite and often dragged the show down. Like Jenny, Vanessa also ended up moving away, as actress Jessica Szohr left the show, and though Szhor is a talented actress, her Gossip Girl character wasn't missed.
10 Lily Van Der Woodsen
Lily van der Woodsen is in Gossip Girl from the beginning to the end, but she’s usually a background player in her daughter Serena’s life. While Lily spends a lot of time saying she wants her children to have more grounded lives, and she appears to be a well-meaning mother, she doesn’t spend a lot of time practicing the same advice she dishes out, which makes sort of makes her and Vanessa opposite sides of the same coin — they both come across as wildly hypocritical.
This is especially true when it comes to Lily's relationship with Rufus. She makes a lot of the same mistakes with him that her daughter makes with Dan, despite having already learned from them when she was in high school. Gossip Girl season 2, episode 24 "Valley Girls" featured actress Brittany Snow as a young Lily in flashbacks that were meant to serve as a backdoor episode for a spinoff series. The spinoff never came to fruition, and though more Brittany Snow is always a good thing, Gossip Girl fans weren't sad to miss out on a show all about Lily.
9 Jack Bass
Blair Waldorf is hardly the kindest person in the world, but she is by and large considered to be the best Gossip Girl character. Therefore, wronging Blair is the biggest cardinal sin another Gossip Girl character can commit. And Jack's sin is worse than most, as he is beyond sleazy in his treatment of Queen B. From the moment he meets her, Jack sees Blair as a conquest and a sex object, and in one of Gossip Girl's most upsetting storylines, he tries to "buy" Blair from Chuck in exchange for a hotel. It's also worth noting that Chuck is no better than Jack, as he agrees to the deal.
In later seasons, Gossip Girl attempts to give Jack somewhat of a redemption arc, as he encourages Chuck to fight for Blair, and he's also the one to tip off the fan-favorite Gossip Girl couple that the police are after them and suggest they get married for spousal privilege — advice that they take. But in terms of Jack's likability, one favor, no matter how big, doesn't forgive what is essentially attempted human trafficking.
8 Georgina Sparks
Georgina Sparks was a Gossip Girl side character with main character energy — at least, according to her. Since her arrival in season 1, Georgina was on a one-woman warpath to mess up the lives of the Upper East Side teens, especially Serena's. But unlike Jenny and Vanessa, whom Gossip Girl fans genuinely wanted off the show, Georgina's chaotic energy was always a welcome storyline and she was a character that audiences loved to hate.
In some ways, Georgina was a combination of Serena and Blair's worst traits. She was a party girl like Serena, though she took her wild-child antics to a whole new level, and Georgina was also a schemer like Blair. However, Blair's scheming, no matter how vicious, was always in the name of keeping herself on top; Georgina was just addicted to destruction. Georgina was in a relationship with Jack Bass at the end of Gossip Girl, and there weren't two characters who deserved each other more.
7 Bart Bass
Bartholomew "Bart" Bass managed to pull off the impossible in Gossip Girl: make Chuck sympathetic. Though Bart's opinion that his son was nothing more than an irresponsible playboy was largely true, there is nothing that Chuck could ever do that would please or impress his father. Bart treated Chuck and the other members of his family like chess pieces, even keeping secret files on them.
Though Gossip Girl fans were no fan of Lily, particularly how she behaved in her relationship with Rufus, nobody could deny that the two had chemistry and were meant to be together. Bart threw a wrench in this and ended up marrying Lily, which broke Rufus' heart and evoked fans' rage. As callous as it may be, nobody was happy to see Bart come "back from the dead", nor was anyone sad when he left Gossip Girl for good.
6 Sage Spence
Over the years, Serena dated several guys, and one of them was Steven Spence, who had a daughter named Sage. Given the age gap between Steven and Serena, she was only four years older than Sage, which can feel awkward and be hard for a child to accept, even a teenager.
But it's hard to feel sympathetic for Sage when she pulls Georgina-level stunts to break up Steven and Serena, which has a ripple effect for Serena and even her friends, like when Sage ruined Blair's fashion show. But ultimately, Sage was not around for long, as Serena and Steven's uncomfortable relationship was mercifully short-lived.
5 Agnes Andrews
While the Gossip Girl fandom was no fan of Jenny Humphrey, it was clear that she was a talented fashion designer, and within her work, she met a model named Agnes Andrews. The two decided to go into business together, which was a mistake on many levels. Agnes was inept and lazy, and for once Jenny was actually in the right when she parted ways with her. Agnes' response — taking all of Jenny’s designs, throwing them into a dumpster, and setting them on fire — said it all.
Jenny was the worst main character, but at least she was still entrenched in the main drama of the show. Seeing anyone other than Blair take Jenny down a peg just wasn't as fun. Ultimately, Agnes was more mean-spirited than ambitious.
4 Diana Payne
While Elizabeth Hurley was among Gossip Girl's starriest guest actors, her character wasn't exactly beloved. Diana Payne was fairly one-note as an intrepid femme fatale keen on seducing Nate and using him and his family to further her career at The New York Spectator.
Nate is hardly the most interesting Gossip Girl character, but that's because the all-American teen never tried to backstab anyone. Seeing someone like Diana go after such an innocent person just isn't fun to watch, and it would have been a better storyline if some of her feelings for Nate were real.
3 Juliet Sharp
Another scheming woman who dated Nate was none other than Juliet Sharp. It turned out that this character’s brother, Ben, was put in prison because of Lily van der Woodsen.
While fighting for a family member’s justice is understandable, Juliet took it way too far. She falsely tipped off Gossip Girl that Serena had an STD and even drugged her. Juliet was so single-minded in her focus on Serena that there wasn't room for any other story with her. She was less of a character and more of an obstacle in Serena's life, albeit a vicious one.
2 Ivy Dickens
When it comes to characters that fans love to hate, Ivy Dickens rivals Georgina. Ivy posing as Serena's cousin (when she was in fact an actress looking to make some extra cash) was one of the biggest scandals in Gossip Girl, but the problem was that Ivy overstayed her welcome.
The cousin lie was a legitimately entertaining storyline, but after that, Ivy just kept randomly popping up for seemingly no other reason than to sew seeds of chaos, whether that was making a move on Dan and telling him to call her Serena or dating the group's dads. At least Georgina was a pot-stirrer who always kept things interesting.
1 The Grimaldis
Proof that royalty doesn't always equal class, the Grimaldis were collectively the worst supporting character in Gossip Girl. Like with Jack, the Monégasque royal family committed the egregious offense of mistreating Blair. Princess Sophie and Beatrice, Louis' respective mother and sister, made it clear that they did not care for Queen B, and thus, the audience didn't care for them.
As for Louis, his fairytale prince act proved too good to be true, and while it's understandable that he was upset about Blair's leaked love confession to Chuck, the fact that he wanted to trap Blair in a loveless marriage was despicable. As vicious as she could be, Blair wanted nothing more than her Prince Charming, and she was luckily able to find her perfect match at the end of Gossip Girl.