This classic teen comedy-drama was based on a book series of the same name by Cecily von Ziegesar and ran from 2007 to 2012. Gossip Girl follows the everyday lives of the Manhattan elite, specifically a group of teenagers who attend a prestigious private school on the Upper East Side. An anonymous blogger called Gossip Girl who documents their every move torments their lives, exposing secrets and scandals. Starring some now big names, including Blake Lively and Penn Badgley, the show still gains new viewers through Netflix and HBO Max. This iconic teen show defined a generation of television.

What made Gossip Girl so great was its extensive array of compelling characters, from rebellious and troubled Chuck Bass (Ed Westwick) to free-spirit Serena (Lively). The various dramas and twists wouldn’t have occurred without this band of privileged and complex teens. Throughout 6 long seasons, the characters underwent years worth of development as they progressed through high school, college, and into the real world. Let’s break down who had the best character arc.


Gossip Girl

Release Date
September 19, 2007

Stephanie Savage, Josh Shwartz


10 Georgina Sparks

Portrayed by Michelle Trachtenberg

Georgina Sparks Gossip Girl
Image via The CW

Michelle Trachtenberg‘s portrayal of the evil, enigmatic Georgina Sparks solidified the character as a fan favorite, despite her constant targeting of the other characters with malice. From her introduction, Georgina’s manipulations and schemes are the cause of major plot points, including Serena’s breakdown in the first season. She even forces Dan (Badgley) to look after her baby, claiming it to be his child. That’s cold. Georgina continues to crave chaos even during her religious phase, and after becoming a mother. She does have some development, though.

When she has a baby, she begins to reevaluate her priorities and aims for a fresh start. But even once she is settled down with a husband, she searches for schemes and gets herself involved with the main group’s dramas. However, as the show progresses, we do see different sides to Georgina Sparks. Somewhere deep down, there is a woman who wants to be loved. As she grows, she makes unlikely alliances with people such as Blair (Leighton Meester). Whether she’s begging for forgiveness or going back to her old tricks, Gossip Girl wouldn’t be the same without this iconic villain.

9 Vanessa Abrams

Portrayed by Jessica Szohr

Jessica Szohr as Vanessa Abrams in Gossip Girl
Image via The CW

Vanessa Abrams (Jessica Szhor) is introduced in season one as an old friend of Dan Humphrey, reappearing when she moves to the city. She is disdained by the superficial Manhattan elite scene and doesn’t warm to the other characters for a while, but eventually finds herself stuck in the middle of the drama. She even dates Nate (Chace Crawford) and has a brief fling with Chuck. Vanessa prides herself on her morals, always wanting to do the right thing. This begins to change throughout the show as she ends up antagonizing certain characters, including Blair, becoming the very thing she hated all along.

Vanessa is one of the more unpopular characters, likely due to her higher sense of self despite being just as morally gray as the rest. But her character arc is still a compelling one, as she portrays a complex individual who gets wrapped up in manipulation despite starting as an outsider. One of her defining moments is when she publishes Dan’s writing about the Upper East Side without his permission, exposing his inner thoughts about his friends. When she begins to not recognize herself, she distances herself from the privileged scene for her own sake. Whether you like her or not, she makes for some great TV.

8 Lily van der Woodsen

Portrayed by Kelly Rutherford

Image via The CW

Lily van der Woodsen (Kelly Rutherford) is the mother of Serena and Eric and a member of the Manhattan elite. She is known for being a distant mother and having many relationships/husbands that affected Serena and Eric’s upbringing. Underneath her air of elegance and sophistication is a history of secrets and scandal. From her perspective, the decisions she makes are to better herself and her children, but this is a cause for trouble. Such as when she had Serena’s teacher put in prison after exaggerating the situation. Lily also has tumultuous relationships that contribute to her arc, including Chuck’s father and Rufus Humphrey (Matthew Settle).

She makes a lot of mistakes throughout the show, mostly having an internal struggle with motherhood. In her relationship with Rufus, he challenges her not only as a parent but as a judgmental individual, as she learns about Rufus’ financial struggles (ignoring the plot hole that the Humphreys were definitely not as poor as they made the audience think). In Lily’s arc, she also faces a complex relationship with her own mom, which comes to a head when she passes away. Lily aims for redemption, and ultimately, she does win back the trust of her children and finds peace.

7 Dan Humphrey

Portrayed by Penn Badgley

Penn Badgley as Dan Humphrey in Gossip Girl
Image via The CW

Everybody’s favorite ‘Lonely Boy’ Dan Humphrey, was the outsider that ended up an insider. Dan attends the school with the others on a scholarship, and comes from a different economic background to them. He gets a foot in the door when he starts dating Serena, and despite having other romantic relationships, this one follows him through his entire arc. Dan tries to keep his integrity as he lives in the world of the Upper East Side, but this falls apart when his career as a writer takes off. He writes about his friends and family, eventually publishing a novel based on their lives.

On top of the novel, it is, of course, revealed in the final season that Dan was Gossip Girl all along. Somehow. This was a spanner in his character arc, as some viewers argued that he had been the same person all along; someone with a superiority complex and a lack of empathy for his friends and family. But others argued it made sense, with the Upper East Side corrupting him. Regardless, his character arc is more akin to an anti-hero. Despite his actions getting worse as the series progresses, the characters still forgive him. And he marries Serena. Joe Goldberg, is that you?

6 Eleanor Waldorf

Portrayed by Margaret Colin

Margaret Colin as Eleanor Waldorf in Gossip Girl
Image via The CW

Eleanor Waldorf (Margaret Colin) is Blair’s mother, and a big name in the fashion industry with her own label named Waldorf Designs. When we first meet Eleanor, she is either passing judgments on Blair or is away on business for weeks at a time. As Gossip Girl progresses, she improves on this slowly. Her life takes a happy turn when she gets together with Cyrus Rose (Wallace Shawn), who is a positive influence on her. Eleanor steps up for Blair when she hits tough times, including her situation with Prince Louis (Hugo Becker) and countless ups and downs with Chuck.

Eleanor’s character arc is a great one to watch unfold. At first, her relationship with Blair is extremely strained to the point that Blair barely even likes or respects her. Due to her social standing and upbringing, Eleanor can be harsh to Blair. As Blair begins to need her support more than ever, Eleanor finally learns to prioritize her daughter and family over her business. Her bond with Dorota (Zuzanna Szadkowski), Blair’s maid, also gets more wholesome as time goes on, specifically when Dorota has babies of her own. Eleanor comes to realize that Dorota basically raised Blair, and once she comes to terms with this, she makes up for lost time and heals.

5 Nate Archibald

Portrayed by Chace Crawford

Nate Archibald- Chace Crawford Gossip Girl
Image via The CW

Nate Archibald (Chace Crawford) is the ultimate golden boy with his life being set up for him. In contrast to his friends, Nate does appear to have a very kind heart, despite being best friends with Chuck Bass. He still makes bad choices, like sleeping with Serena when he was still with Blair. At first, Nate is just a confused kid who doesn’t see eye to eye with his dad. His arc begins when his dad gets involved with drugs, and it leads to him losing everything for a while, including his money.

Above all else, as the show progresses, Nate’s biggest desire is to forge his own path and be in charge of his own decisions. From the hardships with his father, Nate took the opportunity to grow as a person and get to know himself beyond the ‘Nate’ that his father wanted him to be. This compelling arc is sometimes overshadowed by his questionable taste in relationships, but he continues to push himself while remaining a good friend to the rest of the group. Nate manages to make a name for himself in the journalism world, repeatedly rejecting handouts from his grandfather. He ends the show as the only single one, but we can hope he finds true love eventually.

4 Jenny Humphrey

Portrayed by Taylor Momsen

Jenny Humphrey from Gossip Girl standing

Perhaps the most divisive of the characters is Jenny Humphrey (Taylor Momsen), Dan’s younger sister. In season one, she is a sweet kid untainted by the Upper East Side. When she starts to feel immense pressure to fit in, her character begins to break down as she jumps through hoops for Blair, eventually getting herself wrapped up in drama and scandal. At first, she idolizes her peers, until she becomes like them. She even steals a dress from her friend in a moment of desperation. In her darkest moments, Jenny is spiteful and manipulative, even to those who love her.

Her arc is one of the most fascinating, as her sense of self completely changes when she immerses herself in the upper-class lifestyle. It gets worse when her dad dates Lily, as she actively lives on the Upper East Side and has everything at her disposal. As her misgivings pile up, she realizes just how lost she is. Similarly to Vanessa, Jenny distances herself and moves away, rediscovering who she is beyond the facade. She is able to channel her passion and ambition into fashion design, and we see her success in the finale as she collaborates with Eleanor Waldorf.

3 Chuck Bass

Portrayed by Ed Westwick

Chuck Bass portrayed by Ed Westwick looking at Blair Waldorf
Image Via Max

Charles ‘Chuck’ Bass is the epitome of wealth and privilege; this play-boy personifies the debauchery of the Upper East Side. In season one, he is a cold, calculated character that takes any opportunity to talk down on someone or make them uncomfortable. Affected heavily by his father and desperately wanting to impress him, Chuck often acts impulsively. As the show progresses, cracks in his persona begin to show, namely as a result of his relationship with Blair. Falling in love is the Kickstarter of his character arc.

Chuck’s arc is up and down. He takes one step forward, then three steps back. When fans started to love him, he traded Blair for a hotel. That’s cold. His arc isn’t linear, but it is dramatic; by the end, he is an entirely changed man. Chuck is humanized when he loses his father (albeit temporarily), as he jumps into the world of business intending to make his own legacy. And as he matures, he defies all of his own insecurities. And Blair is definitely the best thing that ever happened to him, even if he arguably didn’t deserve it.

2 Serena van der Woodsen

Portrayed by Blake Lively

Serena van der Woodsen Blake Lively smiling
Image via The CW

Serena van der Woodsen is presented to viewers as the perfect IT girl, beautiful, intelligent, and charming. This makes her arc compelling, as the darkness within Serena is unexpected. She moves back to town and starts dating Dan, and is always at odds with Blair. Her past catches up to her with the return of Georgina, and the group finds out about Serena’s regrets, namely her guilt about a friend who overdosed. Her rebellious streak of drinking, doing drugs, and partying comes to an end for good as she, with the help of her friends, lets go of her past.

Her arc as she settles back into a more reserved life is a fascinating example of a privileged woman who does things without consequences. But she is still able to move past it, showcasing resilience as a character. Some viewers still have disdain for Serena, and understandably so. She makes a lot of mistakes but tries to grow from them. Whether you idolize her or hate her, we can’t deny that Serena’s carefree spirit made Gossip Girl what it is, and made up one of the best and most complex friendships with Blair, even if she says ‘I gotta go’ 10 times per episode.

1 Blair Waldorf

Portrayed by Leighton Meester

Leighton Meester as Blair Waldorf (1)
Image via The CW

When we first meet Blair Waldorf, she is a shallow, self-absorbed Queen Bee who wants power and for everyone to fall at her feet. Okay, so that doesn’t really change. However, as the show progresses, Blair grows into a more confident woman. She struggles under the expectations of her mother and wishes to be the perfect version of herself. Things unravel as she hurts those around her, and her relationship with Chuck Bass takes over. She faces setbacks as a consequence of her actions, such as not going to the college she dreamed of. But here, Blair Waldorf finds herself.

Blair arguably goes through the most changes, becoming more likable as you start to understand her character. Blair starts to do things to make herself happy, disregarding the expectations placed on her by her mom and other elites. As she suffers through failures, heartbreak, and disappointment, she is forced into self-reflection and comes out the other side a better person. She even befriends and briefly dates Dan, whom she once despised, as she challenges her prejudices. In the end, Blair prioritizes genuine connection, love and strength over wealth and power. Her journey from judgmental Queen to a confident and independent woman is marked by wins and setbacks, and she remains an iconic and timeless character throughout.

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NEXT: ‘Gossip Girl’: The 10 Main Characters, Ranked By Likability

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