- by Katerina Daley
- – on
- in Lists
The early 2000s was truly the time to be a television watching teen. Formative high school hits such as Dawson’s Creek, Gilmore Girls, One Tree Hill, and The OC dominated the airwaves.
By the late ’00s, however, a noticeable shift in teenage media consumption occurred — and, as a result of it, teen dramas became less about high school and more about excessive wealth and destructive behavior.
Enter Gossip Girl. Premiering in 2007, the series challenged the way teens had been entertained, offering a view of a wealthier world — but also a more technologically savvy one, too.
The series was a soap opera, to be sure, but it was also a mystery and a thriller all along the way, no matter how mind-boggling and, truthfully, stupid a resolution to the mystery the series would eventually offer.
For six melodramatic seasons, Gossip Girl followed the lives of the residents of New York’s Upper East Side, including the members of the Non-Judging Breakfast Club – Blair Waldorf, Chuck Bass, Nate Archibald, and Serena Van Der Woodsen – as they found themselves plagued by an anonymous gossip blogger known only as Gossip Girl.
Just as the residents of the Upper East Side found themselves addicted to every juicy secret, viewers were hooked on the lives of these characters, too.
However, in the long run, how many of those casting choices really worked in the show’s favor?
Here are the 10 Casting Decisions That Hurt Gossip Girl (And 10 That Saved It).
20 Hurt: Penn Badgley (Dan Humphrey)
When Gossip Girl began, Dan Humphrey was your stereotypical outsider who longed to be part of the exclusive inner circle of rich kids and experience the wealth and luxury that was their everyday lives.
By the series’ end, not only was he marrying one of the innermost members of that circle, he had spent six years tormenting each and every member of it by assuming the online identity of Gossip Girl.
He began as a character of modest means and earnest intellect and feeling – but, as a result of existing in so warped and wealthy a world, became a monster who never really faced any consequences for his blackmail and gossip. Instead, he was rewarded with the girl of his dreams, because logic.
It’s not exactly an easy task to play someone who transforms from rags to riches.
However, it’s an even more difficult task to portray someone who goes from innocent bystander to manipulative mastermind – especially when it’s clear that the show never really intended that outcome to happen.
Penn Badgley never really had a chance, due to the volatility of the writing and the clear lack of planning put into it.
However, beyond that disadvantage, he was also never particularly convincing as Dan, the series’ ostensible romantic antihero.
He worked better as Dan, down on his luck, than he ever did as Dan, social climber. But since social climbing proved to be the point of his character, it’s safe to say that the series could have done a better casting job on that one.
19 Saved: Robert John Burke (Bart Bass)
In a series ostensibly about the world of teenage wealth and luxury, it comes as a surprise that some of the most magnetic characters are, in fact, the adults.
Ostensibly removed from that world of teenage foolishness, the parents nevertheless find plenty of ways to get themselves into soapy messes of their own – and perhaps none of them more than the series’ villainous Bart Bass.
A ruthless businessman, Bart’s contentious relationship with his son, Chuck, is one of the series’ central conflicts, resulting in Bart meeting his demise in the final season as a result of a heated argument that puts Chuck under scrutiny due to the compromising nature of their situation at the time.
It would be easy to turn so imposing and singularly evil a character as Bart into a caricature, a glorified mustache-twirling villain with a narrow view of only his dastardly deeds and nothing else.
However, thanks to the gravitas afforded to the role by veteran actor Robert John Burke, Bart’s threatening nature is never one that can be taken lightly.
His presence onscreen looms large, especially opposite his son, and his performance is captivating in each and every dynamic scene.
A veteran of series such as Law and Order: Special Victims Unit and Rescue Me, Burke has more than shown his dramatic power over the years, and it’s not at all wasted in the role of Bart.
18 Hurt: Blake Lively (Serena van der Woodsen)
Serena Van Der Woodsen just may be one of the most spoiled characters in television history. In a world full of privileged and selfish characters, Serena’s behavior is consistently the worst of them all.
She rarely ever thinks of anyone but herself, stealing significant others from so called friends and spreading rumors to enhance her own image.
She’s framed as the girl everyone wants to be or wants to be with, and over the course of the series, she racks up quite the impressive list of exes and enemies.
By series’ end, not only has she not grown in any way whatsoever, but she goes on to marry the man behind the monstrous Gossip Girl moniker, showing that there was never any real depth to the character either.
Blake Lively may be a red-carpet mainstay, and an aspiring lifestyle icon, but in the role of Serena Van Der Woodsen, she couldn’t have been more woefully miscast.
A more capable and talented actress could have found a way to imbue the overall unlikable princes of privilege with moments that garnered potential sympathy.
Instead, Lively spent much of her time as Serena gaping and pouting, over exaggerating emotion for the sake of soap opera theatrics. In recent roles, she has shown herself to be a stronger actress.
However, the years have not been kind to her performance as Serena – or to the character in general.
17 Saved: Kelly Rutherford (Lily van der Woodsen)
As yet another one of the adults who is far more interesting and sympathetic than the teenagers, Lily Van Der Woodsen is everything that Serena Van Der Woodsen could have been.
Over the course of the series, Lily perfectly dances the line between privileged but down to earth. Her romantic relationships are well-written and captivating, particularly with her first love and eventual (ex) husband Rufus Humphrey.
By allowing her to navigate the world of falling in love with someone of a lower socioeconomic class than Serena ever did, the series undercuts its own message of attempting to depict Lily’s daughter in a flattering light.
Lily is effortlessly graceful and unrestrainedly sympathetic, a hard balance to find in the world of so many callous Upper East Siders.
The world of the wealthy and dramatic is one that had long been familiar to actress Kelly Rutherford, who spent much of the 1990s starring on glitzy soap operas including Generations and Melrose Place.
Given her past experience, she brought the necessary poise and grace to the role that a matriarch such as Lily Van Der Woodsen required.
She was able to shift from maternal Lily to self-interested socialite Lily at the drop of a hat, always convincing and able to work well off any costar she was paired with for a plot, no matter how divisive response to the plots themselves may have been.
16 Hurt: Taylor Momsen (Jenny Humphrey)
Dan Humphrey had a difficult enough time fitting in the world of the Upper East Side from the very beginning.
However, if he thought he had it bad, it was nothing compared to what younger sister Jenny Humphrey went through, including attempted assaults, falls from social grace, and spirals into edgy depression that the show tried to convey with the overuse of black makeup.
The character was once promising – a smart and enterprising outsider shows real potential in fashion and her prestigious school – but over time, the series lost the point it was trying to make with her character.
After she spiraled further, the show soon gave up on trying to do anything with her, and actress Taylor Momsen decided to leave the show.
Momsen leaving the show may have been one of the best things to ever happen to it. While she was a perfectly adorable little kid as Cindy Lou Who in the Jim Carrey movie version of How the Grinch Stole Christmas, Momsen’s work as an adolescent actor never came across in a particularly believable way.
Jenny was often criticized by fans for being whiny and annoying, always getting in the way of characters they felt deserved more screen time.
Much of that criticism can perhaps be directly tied to Momsen’s poor acting choices above anything else.
Following her departure from the series, she focused more so on music with her band The Pretty Reckless; and since departing Gossip Girl, she has not acted at all.
15 Saved: Katie Cassidy (Juliet Sharp)
Every good teen soap series needs a whole bunch of characters who are allowed to be truly mischievous villains, and if there was one thing Gossip Girl did well in its twisty run, it was that.
The series had male and female villains alike in spades, most of them embittered socialites who were envious of all that the main group of characters had.
Take, for example, Juliet Sharp – a Columbia student with a vendetta against Serena Van Der Woodsen who will stop at nothing when it comes to bringing her down.
She wins over Serena’s onetime love, Nate, spreads as many rumors about Serena as she can, and generally sabotages her entire public image for some time with incredible ease and accuracy.
While Katie Cassidy may be a divisive actor within the world of the Arrowverse, there is no denying how spot on her portrayal of a scorned wannabe socialite is in the world of the Upper East Side.
Each scene is masterfully acted, whether she is being coy and manipulative as she strings along the likes of the dimwitted Nate Archibald, or whether she is admitting her villainous intentions to the likes of Vanessa, Jenny, or Serena.
Juliet may have struggled to find her place in the scene of Columbia and the New York elite, but Cassidy fit perfectly into a cast that truly could have benefited from her in a larger role.
14 Hurt: Kaylee DeFer (Ivy Dickens)
In the absence of characters such as Jenny and Juliet, Gossip Girl was forced to quickly scramble and find a replacement amoral character who would be able to stir up trouble and get into ill-advised relationships.
Enter the beyond-annoying Ivy Dickens.
As part of an elaborate and aggravating scheme among the Rhodes-Van Der Woodsen family, Ivy first enters the series posing as Serena’s cousin, Charlotte.
When the truth about her identity is revealed, and the wealth she had deceptively inherited is stripped from her, Ivy assumes the role of a true villain, setting out to ruin the Van Der Woodsen clan in any way she can.
Ivy is an original character within the television series, which puts her at a character development disadvantage from the get go.
However, what makes her character most insufferable of all was the choice to cast Kaylee DeFer in the role.
Prior to starring on Gossip Girl, DeFer appeared in a few small movies and roles in low viewed television series; and following Gossip Girl, DeFer hasn’t done much else, even officially announcing a break from acting in 2013.
Based on the generally tone deaf and emotionless performances she turned in during her time as Ivy, that’s perhaps for the best. We’re not sure anyone could have made Ivy an enjoyable character – but DeFer certainly did the character no favors.
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13 Saved: Margaret Colin (Eleanor Waldorf)
Eleanor Waldorf is a hard character to get a handle on. She is at times alternately maternal and cruel.
Over time, she grows a considerable amount, becoming closer to her daughter in her times of need and eventually developing a healthy relationship with her.
However, in the earlier parts of the series, she is downright destructive to her daughter’s sense of worth and self, encouraging her eating disorder and criticizing her body image at every turn.
Thankfully, the series begins to see the error of its ways over time, especially with Cyrus as a mediator among the strong-willed Waldorf women.
Just as Kelly Rutherford’s performance in Gossip Girl was strengthened by her past in the world of soap operas, Margaret Colin was such a standout due to her own soap past.
In the early 1980s, she starred on As The World Turns for three years, originating the role of yet another strong-willed female character, Margo Hughes.
In her tenure as Eleanor Waldorf-Rose, even in her most unlikable moments, Colin was always convincing, providing the perfect amount of grace and composure and gravitas in every scene she shared, whether with her onscreen daughter or her onscreen love.
12 Hurt: Chace Crawford (Nate Archibald)
Nate Archibald isn’t exactly the sharpest tool in the shed or the brightest bulb in the box, but most of the time, he really does have a good heart.
Sure, he can be pretty selfish, as are all of his friends, but he makes the most earnest efforts over the course of the series to put the needs of others before his own.
While that often gets him into trouble – as he gets manipulated easily by seasonal villains, love interests, and friends alike – it also makes him one of the most forward-moving characters in the series.
He has some of the clearest development out of the teen cast, as he transforms from aimless high school student, to newspaper editor, and all the way to candidate for the mayor of New York City.
Nate’s character may be particularly interesting, and overall, he has a pretty compelling narrative on paper. But unfortunately, the interesting aspects of his character are owed entirely to the writing, and not at all to the portrayal by actor Chace Crawford.
Crawford is better taken in small doses. In comedic moments, he’s stronger, and is often quite boyishly adorable.
However, in serious dramatic moments, he always falls flat, never living up to the strength of his onscreen partners.
Nate is shown time and again to be a perfectly malleable character – but perhaps some of that was unintentional and can instead be attributed to the wishy-washy portrayal by Crawford.
11 Saved: Wallace Shawn (Cyrus Rose)
In a show full of so many cutthroat people who are only looking out for themselves, there has to be a character or two who truly represent all things good in the world, even if they’re hard to find within the series’ setting. For Gossip Girl, one of those characters is the adorably affable Cyrus Rose.
As a lawyer to the stars, Cyrus had every reason to let fame and fortune go to his head. However, he never did, instead remaining one of the most down to earth characters in the entire series.
As Blair’s step-father, Cyrus was constantly a source of support, love, and warmth. And with all the positive warm and fuzzy feelings came a little pinch of comic relief, too.
After all, it would be impossible – if not unforgivable – to have the comic genius of the one and only Wallace Shawn in the role of Cyrus Rose and not make him a truly humorous character.
Shawn’s comedic timing and generally adorable old man demeanor make him the perfect choice for a role that was considerably expanded – and softened – from the Cyrus Rose in the Gossip Girl book series.
Shawn provided a welcome veteran talent source to the cast of mostly rising young stars, strengthening their work whenever he shared a scene with them.
10 Hurt: Connor Paolo (Eric van der Woodsen)
The Van Der Woodsen family is a truly dysfunctional bunch, whether you’re considering refined but emotionally complex matriarch Lily, generally disastrous wild child Serena, or any of the number of father figures that have come in and out of their lives.
Among them all, Eric Van Der Woodsen may have been the strongest, despite being the youngest.
Realizing at a young age that he identified as gay, Eric struggled with others’ criticism of him, even briefly being institutionalized due to his identity.
He consistently has a strong sense of himself and is proud of who he is, but later in the series finds himself getting caught up with the wrong crowd, before being written out as attending school in Europe with Jenny.
In many ways, Eric was a revolutionary character at the time, one of the first gay male characters to feature prominently on a popular teen drama series.
However, no matter how innovative and progressive his character itself may have been, the fact remains that his portrayer – Connor Paolo – was never very skilled in his portrayal of the complex emotions and traumas that Eric faced over the course of his young life.
Eric’s strength was portrayed more through the writers’ intentions than through any of Paolo’s interpretations.
9 Saved: Matthew Settle (Rufus Humphrey)
Besides the second season introduction of the recurring Cyrus Rose, Rufus Humphrey is possibly the closest thing Gossip Girl ever offered in terms of a strong, kind father figure.
While he made his fair share of mistakes, and especially in the romantic department (do we really need to relive that Ivy experience?), he always had the best of intentions with his children.
Then again, they did both turn out to be problem children in different ways – with Jenny spiraling into self-destructive behaviors and depressive episodes, and Dan being, well, Gossip Girl.
So maybe, despite having their best interests at heart for the most part, Rufus is perhaps also a cautionary tale about parenting in this world.
Part of what makes Rufus such a strong character is the boyish warmth and charm brought to the role by the incredibly likable Matthew Settle. He plays well on screen opposite both his children, no matter Badgley’s and Momsen’s own limited acting talents.
He also shares considerable chemistry with his on again, off again love interest, Lily, as played by the wonderful Kelly Rutherford.
He is the series’ best representation of the lower end of the socioeconomic spectrum (as far as the series is concerned to display, at least) and shows the potentials of social mobility and integration, all while maintaining his own self and integrity all throughout.
8 Hurt: Desmond Harrington (Jack Bass)
The Bass family truly caused more problems than they were worth throughout the entire run of the series.
However, if you thought Bart Bass was bad, you really hadn’t seen anything at all until you encountered his younger brother, Jack.
Yet another criminal member of the family tree, he runs the portion of the family business in Australia, but frequently visits New York to cause as much trouble for his brother and nephew as he can.
Perhaps what he is most infamous for, however, is an agreement he arranged with his young nephew – in which he would sign over all rights to The Empire to Chuck, if the teenage Blair agreed to spend the night with him.
It would be pretty hard to make Jack a remotely likable character, given how despicable and disgusting he is.
However, by casting the ever reliably cast as a villain Desmond Harrington in the role, Gossip Girl never once gave audiences the chance to wonder what Jack’s intentions would be.
To be fair, he was quite effective in the role, domineering and threatening just as his brother was.
Harrington took his villainy to an over-exaggerated level, though, leaning too heavily into the soap opera-esque nature of the character, while Robert John Burke’s portrayal of Bart never once did.
7 Saved. Zuzanna Szadkowski (Dorota Kishlovsky)
In Gossip Girl, few characters are genuinely, truly good and kind at heart.
The world of the Upper East Side is so focused on ambition and power and financial gains that it’s hard to find someone who truly puts the needs of others above their own needs, or someone who is willing to stand by your side through thick and thin.
For the Waldorf family, they were lucky enough to have not only Cyrus Rose among them, but also their faithful maid Dorota Kishlovsky.
As Blair’s constant supporter and confidant, she was often the mother that Blair lacked, whenever she and her mother were on the outs.
She also proved to be quite the mischievous and reliable ally when the time came for fun schemes to be enacted.
It would have been easy for this series to turn one of its primary maid staff workers into the butt of a joke, or to keep her as a stereotyped, cartoonish character.
However, through the casting of the Polish-American actress Zuzanna Szadkowski, Gossip Girl was lucky enough to avoid falling into those tired tropes.
Szadkowski made Dorota into one of the series’ most iconic characters, full of heart and humor and warmth, and every bit as vital a member of the cast as any of its regular characters.
6 Hurt: Michelle Trachtenberg (Georgina Sparks)
As we’ve already mentioned, Gossip Girl knows how to make a good villain. If anything, the series’ success depends on the need for the core characters to have villains they’re trying to defeat.
Maybe it’s a bit of a laughable concept for a show about spoiled elite teenagers in New York, but nevertheless, villains are lurking at every turn.
One of the show’s earliest of them is Georgina Sparks, a dangerous party girl who arrives in the Upper East Side intent upon causing trouble and danger wherever she goes.
At various points throughout the series, she is alternately fixated on each core member of the group, though her fixation on and twisted joy in tormenting Serena are perhaps the signatures of her character.
Michelle Trachtenberg has a long history of playing polarizing characters who are, more often than not, passionately hated by their series’ respective fan bases.
After spending years as Buffy’s annoying younger sister Dawn on Buffy the Vampire Slayer, Trachtenberg once again got the chance to annoy teen television viewers everywhere as Georgina Sparks – a role so laughably over dramatized in its conception, but one that Trachtenberg still managed to overact in each and every scene.
If there was a female equivalent of mustache twirling cartoonish villains, whatever Trachtenberg decided to do with Georgina Sparks would be it.
5 Saved: Kristen Bell (as Gossip Girl)
The role of Gossip Girl herself – or, as the series finale reveals, himself – is perhaps the most crucial role in the entire series.
As the voice behind the longtime anonymous blogger intent upon wreaking havoc within the Upper East Side, Gossip Girl’s witty commentary keeps both the viewers and the characters within the universe on their toes at all times.
Gossip Girl is uncensored, attacking any and all citizens of the Upper East Side with equal opportunity, and revealing all the dirty little secrets that the public both wants to know about and wishes they never even had a clue about.
Of course, it’s eventually revealed that Dan Humphrey has been Gossip Girl all along, which makes the voice only embodiment of the gossip blogger more than a little confusing when you realize the voice belongs to none other than Kristen Bell.
However, logical leaps aside, the series absolutely hit the jackpot with the casting of Bell.
Having previously spent years offering wry and insightful narration of her own light noir series Veronica Mars, Bell is a pro at the dramatics of narration, making even the most bizarre of situations fascinating as long as she’s the one reading the update.
When Gossip Girl allowed Bell the opportunity to finally appear onscreen in the series finale, that was just the icing on the cake.
4 Hurt: Jessica Szohr (Vanessa Abrams)
In a universe filled with annoying characters who are painfully not self-aware, you’d be hard pressed to find a more obnoxious, ultimately useless characters than the perpetual waste of screen time Vanessa Abrams.
Vanessa offers more of a look at the world of the socioeconomically average, which is something the show struggled with all along.
But while the show tries to portray the insanely wealthy in a positive light, Vanessa is almost constantly viewed negatively, existing as an obstacle or distraction in countless plots that are bogged down and slowed down due to her presence.
Her wit and honesty make her a unique presence within the series, but beyond that, her main function seems to have been to aggravate characters and viewers alike.
Adding to the unbearable nature of Vanessa’s character is the way in which she was so terribly miscast.
Jessica Szohr brings absolutely nothing to the table in an already weak cast of young actors and actresses.
Her delivery of lines alternates between gratingly over-acted and aimless, as though she is barely trying at all.
She never comes across as having any chemistry with the many characters Vanessa is forced into having relationships with. However, thankfully, she exited the series after season four, allowing for a reprieve in the final two seasons much as Jenny’s departure did.
3 Saved: Sebastian Stan (Carter Baizen)
Initially introduced as a grungy gambling college student with a secretive past, Carter is then revealed to have become a humanitarian.
When he’s framed as having stalked Serena, it turns out that he spent the summer with her and supported her through a rough time in her life.
When it’s revealed that he once took advantage of a fellow socialite and her family for the sake of paying off gambling debts, he does everything in his power to make amends and repay them.
Yet since he is so briefly recurring a character, he never gets a full arc or the attention in the narrative that so richly layered a character deserves.
Perhaps part of what makes Carter Baizen such a successful character is the fact that Gossip Girl was ahead of its time in realizing the star power of a young Sebastian Stan.
Riveting and mysterious in each and every scene, Stan’s Carter always has a slight edge to him.
While the show may delight in the illusion of him being an untrustworthy character, only to reveal his many good sides in the end, it’s through Stan’s masterful juggling of emotions that this entire feat is accomplished.
2 Hurt: Ed Westwick (Chuck Bass)
It’s hard to watch Gossip Girl and not walk away without any sort of passionate feelings regarding Chuck Bass.
Some viewers walk away feeling devoted and protective, considering themselves proud Chuck girls who think he’s tortured and misunderstood. Other viewers walk away seething with rage and wondering how a predatory, selfish, cruel man could be portrayed as a suitable romantic hero.
Regardless of what your feelings about him are, it’s clear that Gossip Girl succeeded in creating a character that stands out among the rest of male leads in the genre of 2000s teen television – for better or for worse.
At the time of the series, Chuck’s popularity could be largely attributed to the strength of actor Ed Westwick’s performance.
Skilled at emotional manipulation and genuine emotional displays in equal measure, it was easy to fall sway to Chuck’s charms all while being aware of how despicable he was.
However, recent revelations have now cast Westwick’s performance in an entirely different, harder to stomach light. Within the last year, as a result of the #MeToo movement, multiple women who were once part of the industry have come forward to accuse Westwick of assault.
Any potential enjoyment once derived from Westwick’s performance is therefore fundamentally ruined.
1 Saved: Leighton Meester (Blair Waldorf)
What would Gossip Girl be without its Queen B? We don’t even want to think about it.
Fundamentally fascinating and wonderfully flawed, Blair Waldorf is the true center of the Gossip Girl universe.
As brave as she is brilliant, she overcomes so much in her time on the series, including repeated betrayals from her so-called best friends, betrayals from the so-called love of her life, betrayals from her family… We’re starting to notice a theme here.
However, at the end of the day, Blair is the strongest and the very best of them all.
Inspiring in her independence and commitment to pursuing her dreams of becoming part of the fashion industry, Blair is one of the only characters to emerge from the series as a true icon worth revisiting.
However, as strong as Blair may be on paper, she would have been nothing without the flawless, near effortless portrayal by Leighton Meester.
Arguably the most talented of the young cast of actors whose careers were launched by the series, Meester has long gone overlooked and underappreciated for her work in the series.
In recent years, she has had roles in smaller sitcoms and movies, but that does nothing to dim the brightness of her stardom. She alone made Gossip Girl worth tuning in for. The thought of anyone else filling Blair’s always stylish shoes is the definition of unthinkable.
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Where do you think Gossip Girl went right or wrong with their casting choices? Let us know in the comments!
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