Sarah Michelle Gellar’s performance in the 1999 teen drama Cruel Intentions remains one of the most memorable roles of her career and a defining moment in late-90s cinema. Portraying the cunning, charismatic, and dangerously manipulative Kathryn Merteuil, Gellar delivered a performance that blended elegance, intensity, and dark humor—cementing the character as an enduring pop-culture icon.
Released in March 1999, Cruel Intentions reimagined the classic French novel Les Liaisons dangereuses in an upscale New York City prep-school setting. While the film starred several rising young actors of the era, including Reese Witherspoon and Ryan Phillippe, it was Gellar’s bold transformation from her wholesome Buffy the Vampire Slayer persona that captured the most attention. Her portrayal of Kathryn showcased her versatility and ability to command the screen with a mix of charm and calculated coldness.
More than two decades later, scenes featuring Gellar—especially the famous “makeout scene” with Selma Blair—continue to circulate widely on social media, attracting new generations of viewers. The film’s stylish aesthetic, sharp dialogue, and memorable soundtrack have helped it achieve a cult-classic status, and Gellar’s performance remains central to its lasting appeal.
In recent years, Cruel Intentions has experienced a resurgence in popularity thanks to streaming platforms, anniversary retrospectives, and nostalgic Gen Z audiences. Gellar herself has occasionally revisited the role in interviews, reflecting on the film’s cultural impact and its fearless approach to themes like power, sexuality, and manipulation.
As Hollywood continues to return to ’90s properties, Cruel Intentions stands out as one of the era’s most influential teen dramas—and Sarah Michelle Gellar’s daring performance as Kathryn Merteuil remains a powerful reminder of her talent and range.
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