5 Best Gossip Girl Characters, Ranked

The best thing about “Gossip Girl” — the soapy, steamy series created by Josh Schwartz and Stephanie Savage and very loosely adapted from a book series by Cecily von Ziegesar — is every character is evil. Even if they’re not fully, entirely evil, every person on the show has evil instincts and tendencies, which is precisely what makes the series so fun to watch (and, incidentally, is precisely what ruined the HBO Max reboot; they made everyone way too nice!). With that in mind, when we talk about the “best” characters on “Gossip Girl,” we don’t mean these fictional teenagers and adults are pure of heart or essentially good. Instead, we mean these characters might be conniving schemers and power players, but they’re incredibly fun to watch. (With that said, a few people on this list actually are good, but put a pin in that. We’ll get there.)

When “Gossip Girl” began its run in 2007, we were introduced to a handful of wealthy teens and their even wealthier parents residing on New York’s expensive Upper East Side; the action begins when “it girl” Serena van der Woodsen (Blake Lively) returns to New York after running away a year prior under strange circumstances. As Serena’s friends Blair Waldorf (Leighton Meester), Nate Archibald (Chace Crawford), and Chuck Bass (Ed Westwick) welcome her back with mixed results — Nate declares his love for Serena, Chuck acts like a huge creep, and Blair is angry that her seat as queen bee could be stolen — Brooklyn outsiders and siblings Jenny and Dan Humphrey (Taylor Momsen and Penn Badgley) watch from the sidelines. So which “Gossip Girl” characters do we love to hate and love to watch on screen? Here are the “best” characters on “Gossip Girl,” ranked.

Played by the late, great Michelle Trachtenberg, Georgina Sparks is introduced in the first season of “Gossip Girl” and is the only character who’s not part of the main cast to appear not just in every season, but every season finale; Trachtenberg was even one of the only performers to return for a cameo in the HBO Max reboot. Georgina is, it should be said, the literal opposite of a good person — instead, Georgina is a sneering, conniving, and borderline sociopathic troublemaker whose entire job in the “Gossip Girl” narrative is to cause chaos. That’s precisely why she’s on this list, though.

Any time Georgina shows up on “Gossip Girl,” you know you’re in for a wild ride. Right from the start, she reappears to remind Serena, who’s trying to change and become a better person (boring), of her wild past … and in order to prove that Serena’s still a party girl, she drugs her and drags her along on a crazy night out. After Blair intervenes and has Georgina dismissed temporarily (though not before Georgina pretends to be a random girl named Sarah and seduces Serena’s boyfriend Dan), Georgina keeps showing up to sow discord. Whether she’s surprising Blair as her new roommate at New York University, presenting Dan with a baby and saying it’s his, or casually exposing the secret love child of Dan’s father Rufus Humphrey (Matthew Settle) and Serena’s mother Lily van der Woodsen (Kelly Rutherford) at Rufus and Lily’s long-awaited wedding, she is just an absolute delight. At some point, she even takes up the mantle of the titular anonymous blogger Gossip Girl herself just for fun. Georgina is awful, but in the most delightful, watchable way possible.

In direct contrast to someone as bombastic as Georgina Sparks, Nate Archibald, the “golden boy” of the main group played by Chace Crawford, is … sort of boring. Still, he’s arguably got the purest spirit of anyone on the show; at the end of Season 2, when the gang is trying to figure out Gossip Girl’s identity after a damaging blast made its way through their high school graduation, we learn that Nate has never sent in a tip about any of his friends or loved ones to the mysterious blogger.

That’s why Nate is on this “best” characters list, at the end of the day — he might be a little duller than the other people we’re writing about here, but he’s frankly the only person with any semblance of a moral center. Saying that is a little ironic, though, considering that the entire inciting incident of “Gossip Girl” is a secret romantic tryst between Nate and Serena (atop the iconic Campbell Bar tucked away in Grand Central Station, no less), despite the fact that Nate is Blair’s long-time boyfriend. Still, Nate typically tries to do the right thing most of the time (although even that usually leads to some sort of “Gossip Girl” disaster, as good intentions tend to on this show).

Throughout “Gossip Girl,” Nate dates both Blair and Serena again and brings a bunch of dubious girls into the mix to boot — the funniest of which might be Elizabeth Hurley’s Diana Payne, who wears loud animal prints to signal that she is, in fact, a “cougar” — and while he doesn’t do much else, he doesn’t actively harm anyone. There are more interesting characters on “Gossip Girl,” to be sure, but Nate is actually good, even if it makes him sort of dull.

When we first meet Blair Waldorf, we learn that her father Harold Waldorf (John Shea) left her mother Eleanor Waldorf (Margaret Colin) for a male model named Roman (future “Emily in Paris” star William Abadie), tearing her family asunder. Eleanor, a successful fashion designer, is perfectly happy on her own for a while … but when she meets entertainment lawyer Cyrus Rose (an always welcome Wallace Shawn) in Season 2 of “Gossip Girl,” she falls hard and fast. Blair is aghast; not only is she unwilling to let someone take her father’s place just yet, but she also thinks Cyrus is short and not “hot” enough for her mother, and spends a frankly inordinate amount of time trying to break up Cyrus and Eleanor early in their relationship.

Thankfully, Cyrus wins Blair over in the end, and by the time the show’s second season is over, Cyrus and Eleanor are married and Blair is perfectly happy with her blended family. Shortly thereafter, Cyrus and Eleanor canonically “move to Paris” (seemingly accommodating Colin and Shawn’s otherwise busy schedules by keeping them offscreen most of the time), but whenever Cyrus does show up, he’s a total delight, from his sharp problem-solving to his deep love for Eleanor and his family to his catchphrase “Not enough!” (which he usually says after someone gives him a hug he thinks is too short). Plus, he’s played by Wallace freakin’ Shawn. What more could you want from a great “Gossip Girl” character?!

Besides Cyrus Rose, Blair Waldorf’s maid and closest confidante Dorota Kishlovsky (Zuzanna Szadkowski) is the only “good” character on “Gossip Girl,” but even so, Dorota isn’t above a good scheme. In fact, whenever Dorota does get down and dirty with Blair, it’s a total delight. Dorota, who loves nothing more than a good costume, hails from Poland, and adores Blair even when the girl is wildly misbehaving, isn’t just an essentially kind person, but she’s a blast to watch on screen; it could and probably should be argued that the central relationship of the entire show isn’t between Chuck and Blair or Dan and Serena, but between Dorota and Blair.

Dorota gets some distinct storylines — she falls in love with the doorman at the van der Woodsen’s massive building, Vanya (Aaron Schwartz) and marries him before they have two children — but pretty much all of her storylines are ultimately tied to Blair, which is fine. “Gossip Girl” is a fundamentally unserious show in the very best way, which means that nobody ever thinks particularly hard about why Dorota is allowed to go with Blair to NYU (though it’s never totally clear where Dorota lives during Blair’s admittedly brief stint at the university) or why she has so much free time for scheming when she is, ostensibly, the housemaid of the Waldorf family. None of that matters. Dorota is so great that a popular fan theory about her being Gossip Girl even made it into the show’s series finale; reacting to the in-universe reveal about the blogger’s identity, former New York City mayor Michael Bloomberg exclaims, “I thought it was Dorota!”

You simply cannot write a list about the best characters on the original “Gossip Girl” and not name Blair Waldorf. Portrayed, again, by Leighton Meester — a comedic powerhouse who should really be booked and busy on a near-constant basis — Blair is the clear queen of her high school, Constance Billard, when we first meet her, holding onto her throne thanks to a combination of cruelty and imperious power. (Who could ever forget the time Blair dismissed one of her so-called “minions” by yelling, “Tights are not pants!”) While Blair is a “stereotypical mean girl” on the surface, she has a good amount of inner depth that Meester performs consistently and beautifully; her parents’ divorce shattered her entire world, Eleanor is a mostly absent mother, and when Blair first finds out that Nate cheated on her with her own best friend Serena, she grapples with the fact that she always suspected Nate loved Serena and her own inferiority complex surrounding Serena. 

Throughout “Gossip Girl,” the show affords Meester’s Blair the best outfits, one-liners, and plots (and yes, that does somehow include one where, during one of Blair’s many doomed relationships with Chuck, he “sells” her to his evil uncle in exchange for ownership of a hotel). Even when Blair is behaving like a brat, Meester’s carefully considered and perfectly deployed performance keeps her sympathetic, which is astounding when you consider Blair is probably the show’s most insidious schemer. From calling her ex-boyfriend a “mother-chucker” to the time she proclaims that “destiny is for losers,” Blair isn’t just the best character on “Gossip Girl” — she’s one of the best TV characters in recent memory, and she somehow knows it. As Blair once memorably tells Georgina while running her out of town, “Haven’t you heard? I’m the crazy b**** around here.”