In January 2004,Varietyannouncedthat Warner Bros. Studios would adapt the bestselling book seriesGossip GirlbyCecily von Ziegesarinto a movie. The film would starLindsay LohanofMean GirlsandFreaky Fridayfame as Upper East Side “queen bee” Blair Waldorf. They announced thatAmy Sherman-Palladinowould write the script for the movie, her first major motion picture project. Sherman-Palladino is best known for quick-witted dialogue punctuated with in-the-know pop culture references, best seen in her popular showsGilmore GirlsandThe Marvelous Mrs. Maisel. Though the movie adaptation never happened, it’s safe to say this would have been a very differentGossip Girl.

Gossip Girl

Privileged teens living on the Upper East Side of New York can hide no secret from the ruthless blogger who is always watching.

What Is ‘Gossip Girl’ About?

TheGossip Girlbook series details the sordidlives of privileged teens living in Manhattan’s Upper East Side. The two main characters, Blair Waldorf and Serena van der Woodsen, are the series' central focus. The two leading ladies (played byLeighton MeesterandBlake Livelyin The CW series, respectively) are sometimes BFFs and sometimes enemies. Really, they are the very definition of frenemies. As the teens navigate the treacherous world of the Manhattan social scene, their lives are constantly turned upside down by the anonymous blogger “Gossip Girl.” The gossip-dealing troublemaker constantly sets the gang of Constance Billard School for Girls against each other, then sits back to watch the carnage unfold.

With so many intriguing characters andover-the-top storylines, the book series is better suited to television than film. It’s challenging to imagine cramming the flashy world ofGossip Girlinto just two hours. It takes time to understand and even like the characters ofGossip Girl. However, if any movie adaptation ofGossip Girlcould have been successful, it’s one starring Lindsay Lohan. The early 2000s queen of teen-centered cinema is the ideal choice for a likable mean girl like Blair Waldorf. Throw in the audacious writing of Sherman-Palladino, and it’s fun to think of what could have been.

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Lindsay Lohan Would’ve Been a Totally Different Blair

Lindsay Lohan brings a particularly affable nature to her characters. She is easy to like, even when she isn’t very nice. Take her role inMean Girls, which came out several monthsaftertheGossip Girlannouncement. Her character, Cady Heron, is a naive homeschooled outsider who makes friends with the popular girls at school. Though she plans to expose the “plastics,” the snobby clique made up of Gretchen Wieners (Lacey Chabert), Karen Smith (Amanda Seyfried), and “queen bee” Regina George (Rachel McAdams), Cady instead becomes a mean girl herself. Even as a self-centered egotist, Lohan’s good-natured charm makes Cady likable.

This charismatic appeal could have made Lohan’s Blair perfect for afilm adaptation ofGossip Girl. Right off the bat, Blair would have been more relatable. The meticulous and sophisticated Blair Waldorf is the opposite of the laid-back, effortlessly stylish Serena van der Woodsen. While Serena is calm and collected, Blair seems high-strung and high-maintenance. Those traits make her somewhat unappealing. The only way around that is to either take time to develop her character and show the many facets of Blair’s personality like the TV show does, or use the popularity and instant appeal of a beloved actor such as Lohan to create a connection with the otherwise aloof character.

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The television version of Blair Waldorf is hard to like at first. She is snobbish, cut-throat, competitive, and unapologetic for her mean-spirited antics. She is beautiful and outwardly flawless, but her perfect exterior makes her hard to relate to. It isn’t until the series unfolds that Blair’s inner insecurities are brought to light, making her much more likable and understandable. This works for a television series where character development can evolve over time, and Meester pulls it off with impeccable finesse. However,Lindsay Lohan would have been the ultimate lovable mean girlfor a film version, making her an ideal Blair Waldorf.

Amy Sherman-Palladino Is a Bold Choice for ‘Gossip Girl’

Amy Sherman-Palladino’s writing style is unique.Watch an episode ofGilmore GirlsandThe Marvelous Mrs. Maisel, and it’s easy to see the connection between their writing styles. Both contain punchy, fast-paced, pop-culture reference-packed dialogue. This style works for these quick-witted TV shows, and it’s endearing. Sherman-Palladino’s fast-talking characters fit the premise of their shows perfectly. It makes sense that the quirkyMiriam Maisel (Rachel Brosnahan), who has a talent for delivering scathing, off-the-cuff stand-up, is an overly talkative extrovert. The fast-repartee-style conversations inGilmore Girlsalso work for the youthful mother-daughter relationship that defines the show. But what would a Sherman-PalladinoGossip Girlhave looked like?

Gossip Girl’sBlair Waldorf is certainly sharp-witted. Her intense intellect and trend-setting style lend themselves to a more loquacious Sherman-Palladino iteration. And Lindsay Lohan could have delivered this more verbose version with ease. Lohan’s version ofThe Parent Trapshowcased her ability to handle fast-paced dialogue deftly. However, Sherman-Palladino’s more comedic style does not fit Serena van der Woodsen. Serena’s cool, calm, and collected demeanor doesn’t exactly lend itself to high-energy discourse. It would be an entirely different Serena, (not to mention the otherGossip Girlcharacters) who would wholly have to change with Sherman-Palladino’s writing style.

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What Went Wrong With the ‘Gossip Girl’ Movie?

Sherman-Palladino’s fast-paced dialogue would have givenGossip Girlan entirely different feel. As a movie,Gossip Girlwould have been different no matter what, but more talkative versions of Ziegesar’s beloved characters are hard to imagine. Instead ofa soapy teen dramafilled with intrigue and mystery, a Sherman-Palladino version would feel like a satire rather than an accurate representation of the books. It’s not that this version wouldn’t have worked as a film… it could have been great! But, alas, as is common in Hollywood, theGossip Girlmovie deal fell through.

Properly portraying the lavish lives of the Upper East Side teens takes a certain degree of seriousness and dedication to honoring the unapologetic wealth portrayed in the book series. The wealth and luxury depicted in theGossip Girlbooks are essential to the story. It’s impossible to separate the characters from their opulent surroundings. The characters are who they are becausethey are wealthy beyond compare. We can only envision the teens of Constance flitting around Manhattan, sporting designer duds, and traveling to exotic locations because of their wealth and privilege. Sherman-Palladino does not depict familial riches with reverence. Just look atGilmore Girls. Rory’s grandparents are ultra-wealthy,but their grandiosity is typically seen as something to disdain, not aspire to. For a series about excess,Gossip Girlfans expect a lot of flash and dazzle, perhaps not well suited to Sherman-Palladino.

Rachel McAdams, Lacey Chabert, Amanda Seyfried and Lindsay Lohan in Mean Girls

A fast-talkingGossip Girl, perhaps in the style of a rom-com, with the incomparable Lindsay Lohan in the lead role would have been fantastic. Lohan’s charisma and charm would have made Blair Waldorf instantly likable. Amy Sherman-Palladino would also have brought some exciting elements to aGossip Girlmovie. Her quick-witted banter makes for captivating television, and her unique style would undoubtedly make for a fascinating take onGossip Girl. It’s too bad audiences never got the chance to enjoy this very different version of the beloved book series because it would have been something special. But thank goodnessJosh SchwartzandStephanie Savagedecided to adapt the book series to the small screen and into the outrageous yet lovable TV show we can’t get enough of.The CW’sGossip Girldelivered the drama and luxury of the book series perfectly, and fans wouldn’t change that for anything.

Gossip Girlis available to watch on Max in the U.S.

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Gossip Girl cast dressed in formal wear and posing for a picture on a staircase in front of a red curtain