From Blaire Waldorf to Chuck Bass, which Upper East Sider holds the title of wealthiest character in Gossip Girl?
Gossip Girl remains a staple of 2000s pop culture. The show about a group of overly wealthy, privileged teenagers wreaking havoc on the Upper East Side of New York changed how audiences viewed teen dramas and launched the careers of stars Blake Lively, Leighton Meester, Penn Badgley, and Chace Crawford.
9 Jenny Humphrey 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.
7 Dan Humphrey 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. 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.
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.
4 Blair Waldorf 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.
2 Lily Bass Kelly Rutherford's Lily Bass is the ultimate Manhattan socialite. 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.
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