12 Richest ‘Gossip Girl’ Characters, Ranked

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 Badgleyand 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?”

12 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.

11 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 craves 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.

10 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.

9 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 friendshe 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.

8 Rufus Humphrey

Played by Matthew Settle

Played by Matthew SettleRufus 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.

7 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.

6 Nate Archibald

Played by Chace Crawford

Nate Archibald is the purest, dumbest, nicest character in Gossip Girl. Played by Chace Crawford, the likable character Nate usually avoids all the scheming, instead preferring to focus on his numerous relationships and hobbies. However, he is staunchly loyal, willing to help his cunning lifelong friends whenever they need him.

Out of all the characters in the show, Nate has the most hectic financial life. Originally from old money on his mother’s side, Nate loses his fortune in Season 1 and becomes virtually homeless in Season 2. He then bounces back and ends the show as a successful publishing magnate considering a political career in the grand tradition of his maternal family, proving the apple really doesn’t fall far from the tree.

5 Blair Waldorf

Played by Leighton Meester

Leighton Meester cemented her status as a TV icon with her lauded performance as Blair Waldorf in Gossip Girl. Arguably the show’s true protagonist, Blair is the funniest, most entertaining, and glamorous figure in the Upper East Side. Her notoriously toxic relationship with Chuck Bass, enduring friendship with Serena, and love for deceit and scheming are Gossip Girl‘s major ongoing storylines.

Blair is the daughter of a wealthy lawyer and a successful fashion designer. She later becomes the wife of a literal prince, although she doesn’t receive any money following their separation. However, she ends the show married to a billionaire while leading a fashion empire, meaning she probably has more money than god.

4 Serena van der Woodsen

Played by Blake Lively

Serena van der Woodsen is ostensibly Gossip Girl‘s main character and the queen bee. A wealthy, beautiful, and popular young woman, Serena is the center of attention and the “It Girl” of the Upper East Side. She spends the show exploring several options and career paths without ever settling for one, mainly because her family has so much money she has her life resolved.

Unlike her friends, Serena doesn’t end the show as a major figure in any business. However, she is an heiress, the daughter of a billionaire, and married to a successful novelist. Simply put, Serena doesn’t need to work and probably never will, following her mother’s steps to become the ultimate career socialite in New York City.

3 Lily Bass

Played by Kelly Rutherford

As a show that features the top 1%, Gossip Girl has tycoons, spoiled children, and socialites. One of the most popular socialists in Manhattan is Kelly Rutherford‘s Lily Bass The serial bride married three billionaires before tying the knot with Bart Bass and surely secured juicy settlements each time. She marries Rufus in one of Gossip Girl‘s most rewatchable episodes, but by then, she is already so rich that she can afford to support him, his children, and their children, plus her own.

Lily’s wealth is vast, especially considering Bass Industries is seemingly almighty, and she owns a 20% share of it. Coupled with the money left by her father and other business ventures, Lily is quietly Gossip Girl‘s second-wealthiest character, outranked only by the powerful Bass family.

2 Chuck Bass

Played by Ed Westwick

Chuck Bass is one of the richest characters in Gossip Girl. The cunning libertine with a heart of gold is the show’s main antihero, fighting his self-destructive tendencies throughout the seasons as he tries to become a serious businessman and a worthy partner for Blair Waldorf.

Following his father’s apparent death in Season 2, Chuck inherits his 51% share of Bass Industries. He then begins his own business by buying the Empire Hotel before assuming full ownership of Bass Industries after his father’s second death in Season 6. His growth as a businessman is a part of his character’s narrative, seeing him from managing his father’s empire to creating his own business ventures. Chuck is among the richest people in New York and probably the world, and he reigns supreme as a wealthy character in Gossip Girl.

1 Bart Bass

Played by Robert John Burke

The father of Chuck Bass is a ruthless tycoon who will stop at nothing to make sure that his empire thrives and survives. Played by Robert John BurkeBart Bass is perhaps the richest character in the show up until his second death in the final season. He often shows up in the Gossip Girl storyline as an opposing force to Chuck, which leads them to have a tumultuous and rocky relationship.

In terms of wealth and social status, Bart Bass is portrayed as one of the wealthiest and most powerful figures in the Gossip Girl universe. As the founder of Bass Industries, he is within reach of a company that has a diverse portfolio of assets, such as restaurants, property holdings, and hotels. He also comes from a wealthy and influential family. His social status is further solidified by his connections to other wealthy and influential individuals, cementing his place at the top of the Upper East Side hierarchy.

NEXT: Every Season of ‘Gossip Girl’, Ranked