The iconic '90s thriller 'Cruel Intentions' turns 25: Here they are then and now

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The ICONIC sexy teen thriller Cruel Intentions turns 25 today, and we officially feel like the Crypt Keeper.

Between the late ’90s hair and outfits, the sexy situations—that kiss Sarah Michelle Gellar and Selma Blair has been living rent-free in our heads for more than two decades—and the smoking hot stars, this film sparked queer awakenings for countless ‘90s teens.

Back in 1999, when the film premiered, some cast members were already big stars. Gellar was busy kicking vampire butt, Ryan Phillippe was making a name for himself in teen movies, and Joshua Jackson had landed a starring role on Dawson’s Creek the year prior. It was this star power, along with the quintessential ‘90s styling and naughty, subversive plot that still has us in a choke hold all of these years later.

This modern retelling of Dangerous Liaisons follows wealthy step-siblings Kathryn Merteuil (Gellar) and Sebastian Valmont (Phillippe), who make a devious bet that Sebastian can’t seduce the virginal headmaster’s daughter Annette Hargrove (Reese Witherspoon).

So, as we celebrate the 25th anniversary of this unforgettable film, let’s take a look at where all those stars are today.

Cruel Intentions is currently streaming on Prime Video.

Sarah Michelle Gellar

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When Cruel Intentions came out, Sarah Michelle Gellar was already one of the biggest stars in Hollywood. She had starred in the quintessential ‘90s slasher movies Scream 2 and I Know What You Did Last Summer and was currently starring as a valley girl-turned-vampire hunter in Buffy the Vampire Slayer.

After Cruel Intentions, she went on to star in The Grudge and its sequel, as well as the Scooby-Doo live-action films, and has voiced characters in countless animated series. Most recently she's starred in the Netflix film Do Revenge and the TV show Wolf Pack.

Selma Blair

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In the film, Selma Blair plays Cecile Caldwell, whom Kathryn uses to seek revenge on her ex-boyfriend, Court Reynolds. Cruel Intentions was Blair’s breakthrough role, after which she in Down to You, Legally Blond, The Sweetest Thing, the Hellboy movies, and more recently, American Crime Story: The People vs. O. J. Simpson.

In 2018, Blair revealed she had been diagnosed with multiple sclerosis, which she wrote about in her 2022 memoir Mean Baby: A Memoir of Growing Up.

Reese Witherspoon

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Reese Witherspoon had already been in films like The Man in the Moon and Election when Cruel Intentions thrust her into the limelight. Since then, she’s had a meteoric trajectory, staring in Legally Blonde and its sequel, winning the Academy Award for Best Actress for playing June Carter Cash in Walk the Line, was nominated again for Wild, and more recently has starred in hit shows like Big Little Lies, Little Fires Everywhere, and The Morning Show.

Witherspoon also turned her highly successful book club into a production company called Hello Sunshine, which produces female-led literary adaptations, such as the films Gone Girl and Where the Crawdad Sings and the miniseries Daisy Jones and the Six.

Ryan Phillippe

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After Ryan Phillippe wrapped filming on Cruel Intentions, he starred in a slew of popular movies, including Gosford Park, Igby Goes Down, Crash, and The Lincoln Lawyer, as well as TV shows like Brooklyn Nine-Nine, Will & Grace, and MacGruber. Just last year, he starred in the films The Locksmith alongside Kate Bosworth and Miranda’s Law with Abigail Breslin.

Phillippe and Witherspoon's on-screen romance may have ended tragically, but he ended up marrying his Cruel Intentions co-star. Sadly, the couple divorced in 2008 after having two children together.

Tara Reid

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Tara Reid, who starred as Marci Greenbaum, had landed her first big role the year before Cruel Intentions came out when she played Bunny in The Big Lebowski. 1999 was a banger year for the actress who also starred in American Pie, which premiere just months after Cruel Intentions. She went on to star in the American Pie sequels, National Lampoon’s Van Wilder alongside Ryan Reynolds, all of the Sharknado movies, and, most recently, the drama Of Things Past and the horror film Bloodthirst.

Eric Mabius

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Eric Mabius played Greg McConnell in Cruel Intentions, after which he went on to star as Jenny Shecter’s season one boyfriend, Tim, in The L Word before landing a starring role in Ugly Betty. Since then, he’s been on Chicago Fire and has become a mainstay of the Hallmark channel.

Swoosie Kurtz

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Swoosie Kurtz was an actor long before she starred as Dr. Regina Greenbaum in Cruel Intentions. She had starred in the films Slap Shot, The World According to Garp, and Against All Odd. After she played Dr. Greenbaum — she also portrayed Madame de Volanges in the 1988 film version of Dangerous Liaisons — she went on to star in the long-running TV shows Sisters and Mike & Molly, as well as Pushing Daisies, Man with a Plan, and, most recently, Call Me Kat.

Joshua Jackson

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Joshua Jackson was already a household name when he joined the cast of Cruel Intentions as the frosted-tipped Blaine Tuttle, thanks to starring as fan-favorite Pacey in Dawson’s Creek. He spent the late ‘90s and early 2000s starring in teen thrillers and horror flicks like Urban Legends, The Skulls, Gossip, and Shutter. He then switched back to TV and won the starring roles in Fringe, The Affair, Fatal Attraction, and Dr. Death.

Sean Patrick Thomas

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After playing Ronald Clifford in Cruel Intentions, Sean Patrick Thomas went on to star in hits like Save the Last Dance, Not Another Teen Movie, Halloween: Resurrection, and all three Barbershop movies. He also starred in the TV show The District and, most recently, in Till, Gen V, Reasonable Doubt, and For All Mankind.

Christine Baranski

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Before landing the role of Bunny Caldwell, Cecile Caldwell’s mother, in Cruel Intentions, Christine Baranski starred in The Birdcage and the TV show Cybill. But afterward, her career really took off. She starred in Chicago, both Mama Mia! movies, The Good Wife and The Good Fight, and is currently on the HBO show The Gilded Age.