While HBO’s revival of the show Gossip Girl was short and sweet, the original show continues to attract viewers and remains a staple of 2000s pop culture. Featuring the lives of ostentatiously wealthy, privileged teenagers wreaking havoc on the Upper East Side of New York changed how audiences viewed teen dramas. The show also launched the careers of Blake Lively, Leighton Meester, Penn Badgley, and Chace Crawford — each of whom has become a star in their own right.
A huge reason for the show’s success was its shamelessly excessive approach to wealth. The characters wore designer clothing and lived in gorgeous penthouses and townhouses, presenting a romanticized version of the 1%. Because the characters in Gossip Girl were beyond rich, and while some were richer than others, they all ended the show sitting comfortably atop a mountain of money. That said, viewers keep asking: “Who is the richest in Gossip Girl?”
20
Dorota Kishlovsky
Played by Zuzanna Szadkowski
Dorota was a staple in the Waldorf household in Gossip Girl, often working in the shadows and being protective of her favorite Upper East Sider, Blair. As far as how the working class are treated in a show about the elite, Dorota was loved by the family she worked for and by us, with the Waldorfs even playing a big part in her wedding. She often had the best reactions to whatever antics crossed the Waldorf lobby, playing into the aghast, protective maternal role she embodied for Blair.
Dorota is by no means the wealthiest character in Gossip Girl and is one of the rare working-class characters we see in the show. However, she never really complained about her financial situation, so we can guess that she was probably paid well by Eleanor Waldorf as a maid. She was one of the most consistent characters in the show, probably indicating that her financial situation didn’t change much throughout it, and she continued to live modestly due to her profession (and her husband’s occupation as a doorman). – Jasneet Singh
19
Carter Baizen
Played by Sebastian Stan
Carter Baizen was a whirlwind of a character in the first three seasons of Gossip Girl, from his friends-turned-enemies status with Nate and Chuck, to his chaotic romantic rendezvous with Blair and Serena. At the end of Season 2, he also helped Serena try and track down her father, where Serena ended up caught in Carter’s shadier past. If Carter were around, trouble was close behind.
Though Carter was born into a wealthy family, it was revealed that he had been cut off from his trust fund. However, after developing a serious heroin addiction while traveling, Carter returned to the Upper East Side and engaged in shady business deals to pay off his debts. This came with a price, as his freedom was often threatened, but by the end of his stint in the series, Serena had paid off his debt, certainly leaving him in a better place than he started. – Jasneet Singh
18
Vanessa Abrams
Played by Jessica Szohr
Vanessa arrives in the middle of Season 1 and becomes an integral part of the show. She was never popular with fans, and her storylines often showed her in a somewhat negative light, especially whenever showcasing her jealous, petty, and insecure aspects. That said, she does try her best to be a moral compass in some of the best episodes of Gossip Girl — fearlessly speaking her mind even if it means getting in the way of the elite Upper East Siders.
Unlike most other characters in the show, Vanessa doesn’t become rich throughout the story. She earns considerable money from stealing Dan’s first novel and charging the checks, but she doesn’t gain the same obscene wealth as other characters. Vanessa’s final scene shows her living modestly somewhere in Spain, proving she didn’t finish Gossip Girl better than she started.
17
Jenny Humphrey
Played by Taylor Momsen
Taylor Momsen‘s Jenny Humphrey is widely considered among the most annoying TV characters. Jenny is Dan’s younger sister, a rebellious teen who longed to be popular. After her father marries Lily Bass, Jenny gains the wealth she always craved and rises to become queen of the Upper East Side. However, she meets her downfall as she flies too close to the sun, with Blair Waldorf banishing her for her unsavory behavior.
Jenny leaves the show in Season 3 and only makes sporadic appearances in future seasons. However, she ends the show as a successful fashion designer — she seemingly has her own line under Blair’s larger company. Jenny might not be overly rich, but she surely has more than enough to keep up with her uber-wealthy friends.
16
Penelope Shafai
Played by Amanda Setton
Penelope Shafai is the classic rich mean girl who constantly strives to be the Queen Bee of Constance. Shafai comes from a prestigious and wealthy family who have strong ties in the Manhattan elite community, notably her great-aunt being one of the founders of Hamilton House.
Between her father’s successful business and coming from a family of old money, Penelope has access to a never-ending source of money and seems to always get what she wants, no matter the price. While Penelope isn’t high on the food chain at Constance, her status excels once she attends Columbia University, where her vintage wealth and prominent name open all kinds of doors for her. – Andrea Ciriaco
15
Ivy Dickens
Played by Kaylee DeFer
Ivy Dickens, arguably Gossip Girl‘s least likable character, causes quite a stir when she arrives in Season 4. As a skilled manipulator, she’s not afraid to do whatever it takes to get what she wants, whether it’s infiltrating New York’s high society or pretending to be a van der Woodsen. She sticks around for the last two seasons as one of the show’s primary antagonists while acting as the occasional ally for the group’s schemes.
The Season 5 finale of one of the best 2000s shows sees Ivy receiving Lola’s share of the Rhodes inheritance, which she freely uses throughout Season 6. After being cast away from good following William’s cold rejection, Ivy becomes a best-selling author, and her biography gets turned into a movie. Thus, Ivy finally becomes wealthy on her own, away from the Upper East Side’s poisonous influence.
14
Dan Humphrey
Played by Penn Badgley
Like Jenny, Dan was desperate to belong to the prestigious clique of Serena and company — he just did a far better job at hiding it. He was considered an outsider because he didn’t come from old money and had a modest background. However, Season 6 finally shows Dan’s true colors as a scheming, lying, treacherous, and borderline psychopathic social climber willing to do everything to finally be on the inside.
Played by Penn Badgley, Dan is the one behind Gossip Girl and, thus, the show’s overreaching antagonist. Thanks to his novel “Inside” and a string of scathing exposés about his so-called friends, he becomes quite a successful writer. Dan becomes so rich he can even afford an apartment in Serena’s building! Talk about clawing his way to the top.
13
Rufus Humphrey
Played by Matthew Settle
Played by Matthew Settle, Rufus Humphrey is one of the few adults in the show who make frequent appearances and is central to the storyline. A former musician, Rufus is known for his bohemian-leaning lifestyle and artistic way of living. But with his artistic sensibilities come the struggling artist typecasting, which sees him desiring to keep his creative integrity while still being a part of the Upper East Side community.
In the show, he transforms from a struggling musician to a triumphant gallery owner. After years of being made to feel small due to the sheer wealth of his wife, Lily Humphrey, he eventually finds his footing and financial success. From his humble beginnings, Rufus proves that he wants to become a part of the Upper East Side elite with his determination, humility, and perseverance.
12
Diana Payne
Played by Elizabeth Hurley
Like many of the temporary “villains” in Gossip Girl, Diana brought forth waves of turbulence during her brief stint on the show during Season 5. She kicked off the drama by starting a romance with Nate and then led the chaos into the Bass family’s lives, where she claimed she was Chuck’s biological mother (which turned out to be untrue) and helped Bart disappear while he was presumed dead. As a paragon of seduction, Diana also proved to be somewhat of a mystery, as we still can’t quite pin down who the character is.
She has a long history with the Bass family, which revolved around a high-end sex club that Bart used to own, but eventually climbed the ladder to the successful and wealthy businesswoman she was in the show. She was introduced as the new owner and publisher of the Spectator, a huge newspaper in the Upper East Side. As such, while she was shrouded in mystery, her wealth is still clear as day, and knowing how resourceful she was, after leaving the show, we can imagine she continued a successful career elsewhere. – Jasneet Singh
11
Georgina Sparks
Played by Michelle Trachtenberg
Michelle Trachtenberg‘s Georgina Sparks is among Gossip Girl‘s most popular figures. The villain-turned-fan-favorite appears throughout the show, wreaking havoc everywhere she goes and looking fabulous while doing it. She even makes an appearance in the 2021 reboot of the show, creating chaos for the new students of Constance Billard School for Girls. A childhood friend of Serena, Georgina comes from old money, like the rest of the Non-Judging Breakfast Club.
Georgina marries Philip Becker, a wealthy young man she accepts only because of his fortune, so her son, Milo, can be a legacy at Yale. They eventually divorced, but Georgina, being Georgina, surely arranged for a nice portion of her money to go her way. She seemingly ends the show with Jack Bass, another rich target for her to exploit.
