By Neia Balao
6:04pm PDT, Sep 9, 2022
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The 1999 film "Cruel Intentions" — a modern-day take on the 1988 movie "Dangerous Liaisons," which is based on the 18th century novel "Les Liaisons dangereuses" — served up a deliciously decadent platter of seduction, betrayal and manipulation with a dash of reluctant romance. To celebrate star Ryan Phillippe's 48th birthday on Sept. 10, 2022, Wonderwall.com is checking in on the film's cast to find out what they're up to (and what they look like) more than two decades later.
Keep reading for more on the actresses and actors who played the film's elite Manhattan high schoolers…
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How has Ryan Phillippe's career fared since his tenure as a '90s hottie? He went on to star in films including "MacGruber," "The Lincoln Lawyer" and "The Bang Bang Club." From 2016 to 2018, Ryan starred on the USA Network thriller series "Shooter." The actor, who shares daughter Ava and son Deacon with ex-wife and "Cruel Intentions" co-star Reese Witherspoon — welcomed a third child, daughter Kai, with ex-girlfriend Alexis Knapp in 2011.
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Reese Witherspoon played Annette Hargrove, the sweet and chaste headmaster's daughter who Sebastian tries to seduce. Of course, what starts off as a crude bet soon turns into an unexpected (and tragic) romance.
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Reese Witherspoon's career has continued to flourish! She's starred in several lauded films including "Legally Blonde," "Sweet Home Alabama" and "Walk the Line," for which she earned a best actress Oscar. Reese was recognized as the world's richest actress by Forbes in 2021: Her net worth was estimated at $400 million after she sold a majority stake in her production company, Hello Sunshine, through which she's made many acclaimed projects including series she's starred on like "Big Little Lies," "Little Fires Everywhere" and "The Morning Show." In 2023, Reese will reprise her role as Elle Woods in "Legally Blonde 3." After divorcing "Cruel Intentions" co-star Ryan Phillippe, with whom she has two adult kids, in 2007, Reese — who also owns the clothing company Draper James — married talent agent Jim Toth in 2011; they later welcomed son Tennessee.
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While she portrayed a teenage superhero on "Buffy the Vampire Slayer," Sarah Michelle Gellar took on an entirely different role in "Cruel Intentions." She starred as villainess Kathryn Merteuil, who makes a bet with her stepbrother, Sebastian Valmont (Ryan Phillippe), believing he won't be able to seduce a girl who's saving herself for marriage. At the same time, she sets out to corrupt the preppy and inexperienced Cecile Caldwell.
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Following "Cruel Intentions," Sarah Michelle Gellar continued to star on "Buffy the Vampire Slayer" until 2003. She made a leap to the big screen again in 2002 when she starred in the live-action adaptation of "Scooby-Doo" and also appeared in its 2004 sequel. The same year "Scooby-Doo 2: Monsters Unleashed" debuted, Sarah starred in the cult-classic horror flick "The Grudge." She returned to her small-screen roots when she starred on the short-lived series "Ringer" and "The Crazy Ones." She'll soon be returning to her small screen roots: At Comic-Con in 2022, it was announced that she'll star on the upcoming "Teen Wolf" spinoff series "Wolf Pack" for Paramount+. Sarah — who also founded the company Foodstirs and released a cookbook — married her "I Know What You Did Last Summer" co-star Freddie Prinze Jr. in 2002. The couple has two kids: Charlotte and Rocky.
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Selma Blair starred as sweet and impressionable Cecile Caldwell — Kathryn Merteuil's (Sarah Michelle Gellar) new protégé.
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In 2001, Selma Blair reunited with her "Cruel Intentions" co-star Reese Witherspoon when she portrayed Vivian Kensington, Elle Woods' foe-turned-bestie, in "Legally Blonde." She gained widespread fame when she starred in 2004's "Hellboy" and its 2008 sequel, "Hellboy II: The Golden Army." In 2016, she took on the role of Kris Jenner in the buzzy first season of the FX drama series "The People v. O. J. Simpson: American Crime Story." Selma, who shares son Arthur with ex-boyfriend Jason Bleick, has worked to raise awareness of multiple sclerosis after revealing she was diagnosed with MS in 2018. She and "Cruel Intentions" co-star Sarah Michelle Gellar maintain a close friendship to this day.
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We're not in Capeside anymore! "Dawson's Creek" star Joshua Jackson played Blaine Tuttle, Sebastian's equally conniving friend.
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After "Cruel Intentions," Joshua Jackson accrued even more acting credits, landing starring roles on shows like "Fringe," "The Affair," "When They See Us" and "Little Fires Everywhere." More recently in 2021, he starred as titular neurosurgeon Christopher Duntsch on the crime miniseries "Dr. Death." After his 10-year relationship with actress Diane Kruger ended, Josh wed "Queen & Slim" actress Jodie Turner-Smith in 2019; they welcomed a daughter in 2020.
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Sean Patrick Thomas played Ronald Clifford, Cecile's music teacher who also happened to be in love with her.
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Two years later, Sean Patrick Thomas scored a leading role in a famous early aughts film — 2001's "Save the Last Dance" co-starring Julia Stiles. Sean, who also starred in "Barbershop" and its 2004 sequel, more recently appeared in the 2021 Oscar-nominated historical thriller "The Tragedy of Macbeth." As for his personal life? He's been married to actress Aonika Laurent, with whom he shares two children, since 2006.
