The Beautiful Game of Deceit: Revisiting Cruel Intentions and the Stories It Still Whispers
When Cruel Intentions was released in 1999, it was not just another teen movie, it was a cultural phenomenon. A modern, risk-taking adaptation of Pierre Choderlos de Laclos’s ‘Les Liaisons Dangereuses’, the 1999 film was a contemporary, stylish version dripping ‘Seduction and Sin.’ It passed the ‘nostalgia-test’ in 1999 by covering heart-break and human tragedy in a glossy surface of chanel skirts and antique convertibles. What the fans of the film did not realize was that Cruel Intentions was a scandalous film and that an immature fan base would grow with the movie. It was one of the first films of the 2000s to be associated with a phenomenon of conspiracy theory and ‘whispered’ alternate endings.
A Game Between Angels and Devils
The film centers on ‘step-siblings’ Sebastian and Kathryn, and their pastime. Destruction in the guise of ‘sophistication,’ and manipulation for pleasure by turning the innocent into ‘games’ for their amusement. It was a sick, game of pure ‘evil.’ When Kathryn dares Sebastian to seduce the ‘virginal’ headmaster’s daughter, Annette, Sebastian agrees, drawn by the game and the pure thrill.
The blurred lines of a twisted bet take a different turn when Sebastian falls for Annette. He finds himself ensnared in the emotions he once scorned. When the noose of Kathryn’s deception closes around him, Sebastian’s redemption is too late. He dies saving Annette, and leaves behind a journal to expose Kathryn’s lies.
That final shot— Annette drives away in Sebastian’s vintage Jaguar, his journal on her lap, and The Verve’s “Bitter Sweet Symphony” in the background— became iconic. It is more than a closing scene; it is the ending of innocence, and the victory of truth over decadence. Or so we thought. Fans have debated for years, and with good reason, whether the ending of the film was as clear a statement as it seemed.
Theories and Speculation
Cruel Intentions and other films that stylishly twisted morality cannot escape obsessive fan speculation. In the years after the film’s release, its message boards and early online forums buzzed with the theory that Cruel Intentions was hiding more beneath its glossy veneer.
One prominent theory suggested that Kathryn wasn’t really the villain—she was just a manifestation of the same patriarchal and social structures that she brutally bent to her will. Subtle hints were given to the defenders when Kathryn spoke of “the hypocrisy of society” and how her talent and brilliance were wasted on frivolous contests in a man’s world. “Kathryn wasn’t evil—she was just fighting fire with fire,” one fan wrote in a discussion thread from 2001 that still circulates among Reddit nostalgics.
There is still some speculation that Sebastian didn’t die after all. In the original script, whispers of a hospital scene where he survives, yet is paralyzed, were included. He is punished, after all, but he is still alive. This was never filmed, but director Roger Kumble confirmed in a 2019 interview that early drafts explored “a more ambiguous ending.” He explained, “We ultimately realized it needed to end like a tragedy. The story’s power comes from consequences—without them, it’s just another flirtatious drama.”
Nonetheless, some fans believe Annette’s final smirk in the car signaled she had become more like Kathryn, “a serpent disguised as a saint.” “She’s wearing white, driving the devil’s car, holding the book of sins,” as one theory goes. Even Witherspoon herself once teased the idea in an interview: “We might not think Annette is as innocent as we assume. I mean, who keeps that journal?”
The Offscreen Romance
What made Cruel Intentions so magnetic was not just the scandal but the chemistry as well. Ryan Phillippe and Reese Witherspoon, who met during filming, fell in love and married soon after the movie’s release. This was accompanied by the scandal, of course. Their onscreen tenderness bore an authenticity that couldn’t be faked.
In an interview with Rolling Stone, Phillippe acknowledged that embodying Sebastian led him to confront aspects he found unappealing within himself. He described Sebastian as “manipulative” and “broken,” and what “scared” him the “most” was that he was lonely, paralleling that loneliness with the isolation that brooding intensity, as loneliness, defines the late-’90s antihero with the blend of Sebastion’s charm, cruelty, and heartbreak to shape the era’s cinematic masculinity.
Having just completed Buffy the Vampire Slayer, Sarah Michelle Gellar found in Kathryn a character who allowed her to reverse this hero image. She called it “deliciously freeing” to portray someone without any moral justification. However, filming Kathryn’s breakdown scenes, particularly in the finale where she reveals her drug stash, was highly challenging. Before straining Gellar recited scripts and meditated for hours to find the balance between rage and collapse. “She’s not just caught. She’s stripped of her armor,” she once explained.
To the Gellar, a strong advocate for her cast members, is a source of inspiration for her family members and her partners. Several of them mentioned her positive influence, particularly on challenging all-night shoots. “She was the glue,” Kumble recalled. “Even when she was the villain, she kept the set warm.”
An Unused Script
Not many people are aware that costs were very close to being cut on the production of “Cruel Intentons”. Roger Kumble had a career in playwriting before branching into Hollywood, and Kumble’s adaptation of Les Liaisons Dangereuses was considered by the studios to be “too dark for teens”. Columbia Pictures backed out of the offer for Kumble’s work, citing fear of conservative audience backlash. It was Moritz the Independently financed producer that eventually took the risk touted by Kumble.
The film’s aesthetic was intentional. Kumble remarked how the prep-school and pop-culture were merged creating a unique look. Denise Wingate, the film’s costume designer, remarked how Gellar’s outfits were designed “armour for the modern woman”. The black corsets and designer suits were not just fashion. They were weapons. In contrast, Annette’s wardrobe started in soft colors, but darkened as the story unfolded. This was a symbol of her moral decline.
In filming there were chaotic moments too. Gellar had to regain her composure to continue filming a scene where Kathryn teaches Cecile (Selma Blair) how to kiss. Blair remembers, “It was supposed to be seductive, but we just couldn’t stop giggling.” “Then, when it became a viral talking point, we were shocked. We just thought it was weird and funny.”
The overexposure, the initial backlash, and the cult surrounding it to this day.
The initial hype around the release of Cruel Intentions was extravagant. Pre-release it was promoted as an MTV event with trailers set to Counting Crows and Placebo. Teen magazines called it “a dangerous new kind of love story.” It did modestly during its initial release but saw tremendous success in the home video market. It became a dorm room staples and a defining element of pop culture in the 1990s.
It had the potential to be a cult classic during its time and it was extremely successful in portraying the stakes of adult morality and lust on teenagers. It was a clash of adult morality and teenage lust. It was purely paradoxical. Critics were split. Some called it “porn with pearls” and others “wicked and witty.” It was seen as “wicked and witty” sixteen to twenty years later and characterized as “porn with pearls” during its release in the 1990s. It is frequently and openly noted as the work of Sofia Coppola and Greta Gerwig.
In fandom communities, Cruel Intentions has become something akin to a sacred text, inspiring countless theories, gifs, and essays focusing on themes of power and gender. Kathryn’s mirror scene, in which she applies lipstick as though it were war paint, has become a symbol of unapologetic femininity. “It’s the female gaze looking back,” a fan later wrote on Tumblr. “She’s not performing for men—she’s performing power.”