Cruel Intentions cast: Where are they now?

It's been years since we saw a pair of diabolical step-siblings try to seduce the new headmaster's daughter. See where the stars of the cult classic have ended up.

01 of 13

Still so cruel after all these years

'Cruel Intentions': Where Are They Now?
Columbia Pictures/Courtesy Everett Collection

The sexy and scandalous Cruel Intentions was released on March 5, 1999. Catch up with the cast of the '90s teen classic, decades later, ahead.

02 of 13

Sarah Michelle Gellar (Kathryn Merteuil)

Sarah Michelle Gellar (Kathryn Merteuil)
Bob France/Columbia Pictures; Tibrina Hobson/Getty Images

As she battled the supernatural on cult favorite Buffy the Vampire Slayer, Sarah Michelle Gellar also gave the dark side a shot as the vengeful Kathryn Merteuil in Cruel Intentions. Prior to the film, she'd made a handful of TV appearances — most notably as Sydney Orion Rutledge on Swans Crossing — and earned her first Daytime Emmy award in 1995 for playing Kendall Hart on All My Children before breaking big on the silver screen in 1997's I Know What You Did Last Summer (where she met Freddie Prinze Jr., who she married in 2002).

Aside from her seven-season run on Buffy, Gellar went on to expand her résumé with a variety of roles. She acted in a string of movies throughout the early-2000s, including Scooby-Doo (2002), The Grudge (2004), Southland Tales (2006), and The Air I Breathe (2007). Switching back to TV in 2011, Gellar had a starring part on Ringer and, later, The Crazy Ones. Over the years, she's also supplied voice-overs for the likes of American Dad!, Robot Chicken, The Simpsons, Star Wars Rebels, and Masters of the Universe: Revelation. Gellar has appeared in the 2022 films Clerks III and Do Revenge; scored a starring role on the 2023 Paramount+ series Wolf Pack; and is set to star in and executive produce a limited-series adaptation of Alice Feeney's Sometimes I Lie.

03 of 13

Ryan Phillippe (Sebastian Valmont)

Ryan Phillippe (Sebastian Valmont)
Columbia Pictures/Courtesy Everett Collection; J. Countess/Getty Images

When Ryan Phillippe hopped on board for Cruel Intentions as Gellar's stepbrother-slash-partner-in-crime, Sebastian, he'd already kicked off a budding career. Phillippe debuted on the soap opera One Life to Live in 1992, amassing a handful of TV appearances and laundry list of movie parts throughout the '90s: Crimson Tide (1995), White Squall (1996), I Know What You Did Last Summer (1997) Homegrown (1998), and 54 (1998), among others.

Phillippe has racked up a slew of titles since Cruel Intentions, grabbing film roles in Company Man (2000), Gosford Park (2001), Crash (2004), Chaos (2005), MacGruber (2010), and Setup (2011), plus a costarring spot with Matthew McConaughey in The Lincoln Lawyer (2011). He turned to TV with Damages in 2012, Secrets and Lies in 2015, USA's Shooter from 2016 to 2018, and MacGruber in 2021. (He also appeared in the 2021 premiere episode of Big Sky where his character got killed off.) Phillippe has had parts in other films like Wish Upon (2017), Lady of the Manor (2021), Collide (2022), American Murderer (2022), and The Locksmith (2023).

04 of 13

Reese Witherspoon (Annette Hargrove)

Reese Witherspoon (Annette Hargrove)
Columbia Pictures/Courtesy Everett Collection; Jeff Vespa/WireImage

Witherspoon joined Cruel Intentions as Annette Hargrove, the wholesome headmaster's daughter at the center of Kathryn and Sebastian's scheme. The actress appeared with her then boyfriend, Ryan Phillippe, going on to marry the star just a few months after the release of Cruel Intentions, though they divorced eight years later. She acted alongside a number of big names beforehand, making her debut in 1991's The Man in the Moon with Sam Waterston and Gail Strickland. Other '90s titles include Fear (1996), Pleasantville (1998), and Twilight (1998).

Witherspoon continued to achieve critical and commercial success, starring in American Psycho (2000), Legally Blonde (2001), and Sweet Home Alabama (2002). In 2005, she won an Academy Award for her performance as June Carter in the Johnny Cash biopic Walk the Line. She's since racked up various leading roles, including spots in Four Christmases (2008), Water for Elephants (2011), Mud (2012), Wild (2014) — which earned her a Best Actress Oscar nomination — Home Again (2017), A Wrinkle in Time (2018), and Your Place or Mine (2023). She stars alongside Jennifer Aniston and Steve Carell on Apple TV+'s The Morning Show.

At the helm of her media company, Hello Sunshine, Witherspoon has expanded her résumé as a producer, as well as an actor, in the HBO limited series Big Little Lies and in the Hulu miniseries Little Fires Everywhere. She's also produced blockbuster films like Gone Girl (2014) Lucy in the Sky (2019), and Where the Crawdads Sing (2022), as well as executive produced Amazon Prime Video's 2023 miniseries Daisy Jones & the Six.

05 of 13

Selma Blair (Cecile Caldwell)

Selma Blair (Cecile Caldwell)
Columbia Pictures/Courtesy Everett Collection; Jason LaVeris/FilmMagic

Save for sizable parts in Strong Island Boys (1997) and Brown's Requiem (1998), Selma Blair had mostly earned small or uncredited parts before being cast in Cruel Intentions, which was largely considered her breakthrough role. She played Cecile Caldwell, one of the wealthy socialites Sebastian must seduce if he wants to score with Kathryn.

Blair picked up a title spot on the WB's Zoe, Duncan, Jack & Jane just before Cruel Intentions debuted. She stuck with the series for two years, then dipped back into movies for roles in Legally Blonde (2001), The Sweetest Thing (2002), A Guy Thing (2003), and Hellboy (2004). Blair has hit TV with gigs on Kath & Kim, Web Therapy, Anger Management, The People v. O.J. Simpson: American Crime Story, and Another Life. In late 2018, she announced that she had been diagnosed with multiple sclerosis; making an emotional return to the red carpet at the 2019 Vanity Fair Oscars party. Blair remains active in Hollywood, booking roles in After (2019), After We Collided (2020), and Far More (2021), and competed on Dancing With the Stars in 2022. She unfortunately had to drop out out of the dance competition series due to health concerns, but performed once more for the season finale.

06 of 13

Louise Fletcher (Helen Rosemund)

Louise Fletcher (Helen Rosemund)
Columbia Pictures/Courtesy Everett Collection; Gabriel Olsen/Getty Images

Louise Fletcher had an impressive career behind her before claiming title of Sebastian's aunt Helen in Cruel Intentions. Starting in 1958, she made a slew of TV and movie appearances before launching to international stardom for her role in 1975's One Flew Over the Cuckoo's Nest as Nurse Ratched. The gig earned Fletcher an award trifecta, making her the third actress to win an Oscar, BAFTA, and Golden Globe for a single performance. She went on to act in a lengthy list of films and shows ahead of Cruel Intentions, including Brainstorm (1983), Firestarter (1984), Flowers in the Attic (1987), and TV series Picket Fences and Star Trek: Deep Space Nine.

Post-Cruel Intentions, Fletcher continued to take on many roles, with a heavier nod to TV in the 2000s. She snagged cameos on 7th Heaven, ER, Heroes, and Private Practice, picking up an Emmy nomination for her guest role on Joan of Arcadia. The late actress also played Frank Gallagher's (William H. Macy) hard-edged mother on the Showtime comedy Shameless and appeared in two episodes of Netflix's Girlboss, which was her last acting role before she died in September 2022 at 88 years old.

07 of 13

Joshua Jackson (Blaine Tuttle)

Joshua Jackson (Blaine Tuttle)
Columbia Pictures/Courtesy Everett Collection; Walter McBride/Getty Images

Joshua Jackson may have made a name for himself as Dawson Leery's charming best pal Pacey on Dawson's Creek, but his onscreen credits begin long before that. He first put himself on the map as The Mighty Ducks' Charlie Conway in 1992, grabbing several TV roles before locking in Dawson's Creek in 1998 and Cruel Intentions the following year. He played Sebastian's sordid accomplice Blaine, tricking Annette's ex-boyfriend into bed as blackmail.

Following his five-year run on Dawson's Creek, Jackson starred in films like Aurora Borealis (2005), Shadows in the Sun (2005), and Bobby (2006). In 2008, he scored the part of Peter Bishop on Fringe, after which he slid directly onto Showtime drama The Affair from 2014 to 2019. Jackson then appeared in Ava DuVernay's Netflix limited series When They See Us, as well as in Little Fires Everywhere and Dr. Death. He stars in the 2023 Paramount+ series adaptation of Fatal Attraction.

08 of 13

Eric Mabius (Greg McConnell)

Eric Mabius (Greg McConnell)
Columbia Pictures/Courtesy Everett Collection; J. Countess/Getty Images

Eric Mabius played Greg McConnell, the football stud whom Sebastian and Blaine suspect of leaking Sebastian's bad-boy rep to Annette. Before coming into the Cruel Intentions gig, Mabius appeared in a range of indie flicks, from Welcome to the Dollhouse (1995) and Black Circle Boys (1997) to The Minus Man (1999).

Mabius worked primarily in movies in the early-'00s, most notably as activist-turned-cop Matt Addison in Resident Evil (2002). He switched his focus to TV around 2005 with a stint on The O.C., going on to take roles on Eyes, The L Word, Ugly Betty, and Chicago Fire. Mabius also stars as Oliver O'Toole in the Hallmark Movies & Mysteries film series Signed, Sealed, Delivered.

09 of 13

Sean Patrick Thomas (Ronald Clifford)

Sean Patrick Thomas (Ronald Clifford)
Columbia Pictures/Courtesy Everett Collection; Earl Gibson III/WireImage

Cruel Intentions was the first big film for Sean Patrick Thomas, who'd previously picked up bit parts in Courage Under Fire (1996), Conspiracy Theory (1997), Picture Perfect (1997), and Can't Hardly Wait (1998) before the movie's release. As music teacher Ronald Clifford, hopelessly in love with his student Cecile, he played an integral part in Kathryn and Sebastian's ploy to deflower the teen.

Just two years later, Thomas earned his first leading role in the 2001 romance flick Save the Last Dance, starring opposite Julia Stiles. He went on to appear in Barbershop (2002), Halloween: Resurrection (2002), The Fountain (2006), Barbershop: The Next Cut (2016), The Curse of La Llorona (2019), and Till (2022), plus TV series The District, Reaper, Ringer, and Reasonable Doubt.

10 of 13

Christine Baranski (Bunny Caldwell)

Christine Baranski
Columbia Pictures/Courtesy Everett Collection; Monica Schipper/FilmMagic

Aside from her assortment of roles in television and film throughout the '80s and '90s, Christine Baranski also bolstered her résumé on Broadway before playing Cecile's prim mother, Mrs. Caldwell, in Cruel Intentions. She picked up Tonys for her performances in The Real Thing (1982) and Rumors (1988), earned high praise for her part as Katherine Archer in the 1996 film comedy The Birdcage, and did a three-year run on Cybill as the boozed-up Maryann Thorpe.

Baranski continued to thrive after Cruel Intentions, booking parts in How the Grinch Stole Christmas (2000), Chicago (2002), Mamma Mia! (2008) — as well as the 2018 Mamma Mia! sequel, Mamma Mia! Here We Go AgainInto the Woods (2014), and A Bad Moms Christmas (2017), in addition to recurring roles on Happy Family, The Big Bang Theory, and The Good Wife. She starred on the Good Wife spin-off series The Good Fight from 2017 to 2022, and costars alongside Carrie Coon and Cynthia Nixon as Agnes van Rhijn on HBO Max's The Gilded Age.

11 of 13

Tara Reid (Marci Greenbaum)

Tara Reid (Marci Greenbaum)
Tibrina Hobson/Getty Images

Tara Reid had been acting for years by the time she joined Cruel Intentions as Marci Greenbaum, the daughter of Sebastian's therapist. She appeared in a mass of commercials as a child, later doing a stint on Days of Our Lives and landing her breakout gig as Bunny in The Big Lebowski (1998).

Reid hit screens as Vicky Lathum in American Pie (1999) just months after Cruel Intentions debuted. She went on to pick up spots in several comedies, including Josie and the Pussycats (2001), Van Wilder: Party Liaison (2002), and on the Zach Braff-led Scrubs. She has starred in the Syfy franchise Sharknado since the series' first installment in 2013, and appeared in a 2023 episode of CBS' Ghosts.

12 of 13

Charlie O'Connell (Court Reynolds)

Charlie O’Connell (Court Reynolds)
Columbia Pictures/Courtesy Everett Collection; Michael Stewart/WireImage

Charlie O'Connell played Kathryn's ex-boyfriend Court Reynolds, the fuel behind her vindictive plot. Prior to Cruel Intentions, he most notably appeared on the sci-fi fantasy series Sliders as scientist Colin Mallory.

O'Connell continued his big-screen turns with Dude, Where's My Car? (2000), Kiss the Bride (2002), and The New Guy (2002), but many fans will recognize him from his season 7 run on The Bachelor.

13 of 13

Herta Ware (Mrs. Sugarman)

Herta Ware (Mrs. Sugarman)
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Herta Ware's role as the forgetful Mrs. Sugarman in Cruel Intentions was one of her last. The then-81-year-old made several stops on TV throughout her career, including Knots Landing, Highway to Heaven, The Golden Girls, ER, and Beauty and the Beast. She appeared in a number of movies as well, including The Black Marble (1980), Cocoon (1985), and Practical Magic (1998).

Ware closed out her career with parts in Held Up (1999), Desperate but Not Serious (1999), and Beautiful (2000). She died at the age of 88 in 2005.

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