Gossip Girl: Top 12 Supporting Characters That Stirred Up the Most Controversy

Summary

Jenny Humphrey lost herself in her quest for popularity and became one of the most hated characters in Gossip Girl.

Vanessa Abrams fell short of fulfilling her potential as a relatable advocate against wealth and privilege, ultimately coming across as a hypocrite. Both Lily van der Woodsen and Vanessa demonstrated hypocritical behavior by dispensing advice they themselves failed to abide by, thus diminishing their likability.

While Blair Waldorf, Chuck Bass, and their affluent comrades may not be the most beloved individuals, the supporting characters in Gossip Girl take the cake for being the worst. Adapted from the book series by Cecily von Ziegesar, the show revolves around a clique of privileged teenagers residing in New York City's Upper East Side. Their personal affairs are both documented and criticized by the elusive blogger known as Gossip Girl. The series aired for six seasons between 2007 and 2012 and even spawned a short-lived reboot on Max (formerly known as HBO Max) in 2021.

Gossip Girl catapulted its main cast into stardom, particularly Blake Lively as Serena van der Woodsen and Penn Badgley as Dan Humphrey. However, the teen drama also served as a platform for guest actors to leave their mark, whether as school rivals or love interests for the main characters. Some actors even had small roles on Gossip Girl prior to achieving fame, such as Sebastian Stan as Carter Baizen and Rachel Brosnahan as an unnamed "Girl." Unfortunately, not every supporting player was adored by the show's fans, and many unintentionally found themselves competing for the title of the most despised character in Gossip Girl.

12 Jenny Humphrey

Many people harbored dislike for Little J, despite her hailing from a genuinely kind and ordinary family on the show. Her utmost desire was to belong in school and ascend from Brooklyn to become the reigning queen of Constance. In pursuit of this goal, she lost sight of herself and seemed unconcerned about the harm she inflicted upon her loved ones and herself. She engaged in theft, deceit, skipping classes, adopted the behavior of a mean girl, and completely shut out those who already appreciated the original, authentic Jenny.

The problem with Jenny's descent into a would-be villain was its abruptness. It was as if she were two separate individuals: the innocent and charming Little J, and the ruthless betrayer. Additionally, Jenny made audacious attempts to usurp Blair's influential position, which the audience adored Blair Waldorf as Queen B. When Taylor Momsen made the decision to depart from the show, it resulted in Jenny's most humbling exit in Gossip Girl history. Blair essentially banished her from Manhattan, which may have reflected the sentiment of the audience.

11 Vanessa Abrams

Vanessa Abrams, a supposed likable character, failed to live up to expectations. Despite claiming to dislike the wealthy Upper East Side, Vanessa never seemed to leave it and even dated one of the richest individuals, Nate Archibald. Gossip Girl missed a chance to address wealth and privilege through Vanessa, ultimately making her appear as a hypocrite.

In addition to Nate, Vanessa also dated Dan, but their chemistry did not compare to Dan's connection with Serena, crushing audience hopes for their childhood crush to succeed. Compared to Serena and particularly Blair, Vanessa's storylines lacked excitement and often dragged the show's momentum. Similar to Jenny, Vanessa eventually departed from the show as actress Jessica Szohr left, but her absence had little impact since her character did not resonate with the viewers.

10 Lily Van Der Woodsen

Lily van der Woodsen is a consistent presence in Gossip Girl, but she typically takes a backseat in her daughter Serena's life. Although Lily often claims that she wants her children to have stable lives, and she appears to be a well-intentioned mother, she fails to follow her own advice, making her quite similar to Vanessa in terms of hypocrisy.

This is particularly evident in Lily's relationship with Rufus. She repeats many of the same mistakes with him that her daughter makes with Dan, despite already learning from them during her own high school years. In Gossip Girl Season 2, Episode 24 "Valley Girls," actress Brittany Snow portrays a young Lily in flashbacks that intended to serve as a pilot episode for a spinoff series. Unfortunately, the spinoff never materialized, and while more Brittany Snow is always welcome, Gossip Girl fans weren't disappointed to miss out on a show solely centered around Lily.

9 Jack Bass

Blair Waldorf is not known for her kindness, but she is widely regarded as the most beloved character in Gossip Girl. Therefore, crossing Blair is the ultimate sin among the other characters. And Jack's transgressions against her are particularly heinous, as he treats Queen B with complete disrespect. From their first encounter, Jack views Blair as a conquest and objectifies her, and in one of Gossip Girl's most disturbing storylines, he attempts to "purchase" Blair from Chuck in exchange for a hotel. It's important to note that Chuck is also complicit in this terrible act.

In later seasons, Gossip Girl tries to redeem Jack by showing him supporting Chuck in fighting for Blair. Additionally, Jack tips off the fan-favorite Gossip Girl couple that the police are after them and suggests they get married for spousal privilege - advice they act upon. However, despite these favors, Jack's likability remains questionable, as these actions cannot excuse his involvement in what essentially amounts to human trafficking.

8 Georgina Sparks

Georgina Sparks was a Gossip Girl side character who exuded the charisma of a main character, or so she believed. From the moment she arrived in season 1, Georgina made it her mission to wreak havoc on the lives of the Upper East Side teens, particularly Serena's. Unlike Jenny and Vanessa, who viewers hoped would exit the show, Georgina's tumultuous energy was always a captivating storyline, making her a character that audiences loved to despise.

In many ways, Georgina embodied the worst qualities of both Serena and Blair. Like Serena, she was a party girl, though she took her rebellious antics to an extreme level, while also possessing Blair's penchant for manipulation. However, Blair's scheming, however ruthless, always served the purpose of maintaining her own status, whereas Georgina simply thrived on chaos. In the end, Georgina ended up in a relationship with Jack Bass, a pairing that seemed destined considering their shared disposition for mayhem.

7 Bart Bass

Bartholomew "Bart" Bass accomplished the impossible in Gossip Girl by eliciting sympathy for Chuck. While Bart's belief that his son was merely an irresponsible playboy held some truth, Chuck could never satisfy or impress his father, regardless of his actions. Bart treated Chuck and his family as pawns, even keeping secret files on them.

Despite fans' disapproval of Lily, especially regarding her behavior in her relationship with Rufus, it was undeniable that they had chemistry and were destined to be together. Bart disrupted this and ultimately wedded Lily, breaking Rufus' heart and enraging fans. Although callous, no one rejoiced at Bart's return from the dead, nor did they mourn his permanent departure from Gossip Girl.

6 Sage Spence

Over the years, Serena had been involved with multiple partners, one of them being Steven Spence, who had a daughter named Sage. Given the significant age difference between Steven and Serena, the fact that Serena was only four years older than Sage could create an awkward and challenging situation for the child, even considering she was a teenager.

However, it becomes difficult to sympathize with Sage when she resorts to schemes similar to those of Georgina to separate Steven and Serena. These actions have a ripple effect on Serena and even her friends, like the time when Sage disrupted Blair's fashion show. Fortunately, Sage's presence in their lives was short-lived, as Serena and Steven's uncomfortable relationship didn't last long.

5 Agnes Andrews

Despite Jenny Humphrey's unpopularity among the Gossip Girl fandom, her talent as a fashion designer was undeniable. During her work, she crossed paths with a model named Agnes Andrews, and the two made the ill-advised decision to embark on a business venture together. It quickly became evident that Agnes was lacking in both skill and motivation, leading Jenny to make the justified choice of parting ways with her. Agnes' extreme reaction of discarding all of Jenny's designs into a dumpster and setting them ablaze spoke volumes about her character.

Although Jenny may have been the least liked main character, she remained a central figure in the main drama of the show. Witnessing someone other than Blair humble Jenny just did not provide the same amusement. Ultimately, Agnes proved to be more malicious than driven by ambition.

4 Diana Payne

Elizabeth Hurley made a guest appearance on Gossip Girl, but her character, Diana Payne, was not well-liked. Diana was portrayed as a one-dimensional femme fatale who was determined to seduce Nate and exploit his family to advance her own career at The New York Spectator.

While Nate may not be the most captivating character on Gossip Girl, it was disappointing to see someone like Diana target such a innocent person. It would have been more engaging if there had been genuine feelings between Diana and Nate, making their storyline more compelling.

3 Juliet Sharp

Juliet Sharp, another conniving woman in Nate's dating history, had a surprising connection to the imprisonment of her own brother, Ben, courtesy of Lily van der Woodsen.

Though it's understandable to fight for justice for a family member, Juliet took her vendetta to extremes. She maliciously alerted Gossip Girl with false information about Serena having an STD and went as far as drugging her. Juliet's relentless fixation on Serena left no room for any other narrative in her life. Rather than a fully developed character, she became nothing more than a formidable hindrance in Serena's journey.

2 Ivy Dickens

Ivy Dickens, notorious for being a character that fans love to hate, gives even Georgina a run for her money. Ivy, who cunningly masqueraded as Serena's cousin while actually being an actress seeking to make a quick buck, ignited one of the most shocking scandals in the realm of Gossip Girl. However, the issue was that Ivy outstayed her welcome.

While the initial storyline involving her deceitful cousin act proved to be genuinely captivating, Ivy's recurring appearances became increasingly sporadic and devoid of purpose, merely serving to sow seeds of chaos. Whether it was making advances towards Dan and insisting he call her Serena, or embarking on relationships with the fathers of the group, Ivy seemed determined to disrupt the status quo. In contrast, Georgina consistently stirred the pot and infallibly ensured that things remained interesting.

1 The Grimaldis

Proving that being royalty doesn't always equate to having class, the Grimaldis were undoubtedly the most unsupportive characters in Gossip Girl. Similar to Jack, the Monégasque royal family committed the reprehensible act of mistreating Blair. Princess Sophie and Beatrice, Louis' mother and sister respectively, made it abundantly clear that they had no regard for Queen B, leading the audience to feel the same way.

Regarding Louis, his portrayal as the ideal prince was ultimately too good to be true. While it's understandable that he was deeply hurt by Blair's leaked love confession to Chuck, his desire to trap her in an unfulfilling marriage was truly despicable. Despite her own flaws, Blair yearned for nothing more than to be with her Prince Charming, and fortunately, she was able to find her perfect match in the end of Gossip Girl.