Still so Cruel after all these years
The sexy and scandalous Cruel Intentions celebrates its 20th anniversary March 5. Catch up with the cast of the ’90s teen classic, two decades later, ahead.
Sarah Michelle Gellar (Kathryn Merteuil)
THEN: As she battled the supernatural in 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 cameos — most notably as Sydney Orion Rutledge on Swans Crossing — before breaking big on the silver screen in 1997’s I Know What You Did Last Summer.
NOW: Aside from her eight-year run on Buffy, Gellar went on to expand her résumé with a variety of roles. She picked up a Daytime Emmy Award for her two-year stint as Kendall Hart on All My Children, and appeared 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). She switched back to TV in 2011 with a starring part in 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, and Star Wars Rebels. She’s currently set to star in and produce a limited-series adaptation of Alice Feeney’s Sometimes I Lie.
Ryan Phillippe (Sebastian Valmont)
THEN: When Ryan Phillippe hopped on board Cruel Intentions as Gellar’s step-brother-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, hitting a handful of TV appearances and a 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.
NOW: Phillippe has racked up a slew of titles since Cruel Intentions, grabbing roles in Company Man (2000), Gosford Park (2001), Crash (2004) Chaos (2005), MacGruber (2010), and Setup (2011), plus a co-starring spot with Matthew McConaughey in The Lincoln Lawyer (2011). He turned to TV with 2012’s Damages and 2015’s Secrets and Lies, and starred on USA’s Shooter from 2016 to 2018.
Reese Witherspoon (Annette Hargrove)
THEN: 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).
NOW: 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), and Wild (2014), the last of which earned her a Best Actress Oscar nomination. She is set to star alongside Jennifer Aniston and Steve Carell on Apple’s The Morning Show.
At the helm of her media company Hello Sunshine, Witherspoon has expanded her resumé as a producer as well as an actor in recent years, including on Wild and the HBO series Big Little Lies, in which she also stars.
Selma Blair (Cecile Caldwell)
THEN: Save for sizeable parts in Strong Island Boys (1997) and Brown’s Requiem (1998), Selma Blair had mostly earned small or uncredited roles 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.
NOW: 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). In recent years, she’s hit TV with gigs in Kath & Kim, Web Therapy, Anger Management, and The People v. O.J. Simpson: American Crime Story. In late 2018, she announced that she had been diagnosed with multiple sclerosis; she made an emotional return to the red carpet at the 2019 Vanity Fair Oscars party.
Louise Fletcher (Helen Rosemund)
THEN: Louise Fletcher had an impressive career behind her before claiming title as 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 Wars: Deep Space Nine.
NOW: Post-Cruel Intentions, Fletcher continued to take on many roles, with a heavier nod to TV in the 2000s. She snagged cameos in 7th Heaven, ER, Heroes, and Private Practice, picking up an Emmy nomination for her guest roles on Joan of Arcadia. Most recently, she played Frank Gallagher’s hard-edged mother on the Showtime comedy Shameless and appeared in two episodes of Netflix’s Girlboss.
Joshua Jackson (Blaine Tuttle)
THEN: 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 in 1998 and Cruel Intentions the following year. He played Sebastian’s sordid accomplice Blaine, tricking Annette’s ex-boyfriend into bed as blackmail.
NOW: Following his five-year run on Dawson’s, 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, sliding directly into Showtime drama The Affair in 2014. In 2019, he will appear in Ava DuVernay’s upcoming Netflix limited series When They See Us.
Eric Mabius (Greg McConnell)
THEN: 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).
NOW: 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 in Eyes, The L Word, Ugly Betty, and, more recently, Chicago Fire.
Sean Patrick Thomas (Ronald Clifford)
THEN: Cruel Intentions was the first big film for Sean Patrick Thomas, who’d previously picked up bit parts in Courage Under Fire, Conspiracy Theory, Picture Perfect, and Can’t Hardly Wait, 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.
NOW: Just two years later, Thomas won 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), and The Fountain (2006), plus TV series The District, Reaper, and Ringer. He will appear next in the horror film The Curse of La Llorona.
THEN: Aside from her assortment of roles in television and film throughout the ’80s and ’90s, Christine Baranski also bolstered her resumé 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 1996 comedy The Birdcage, and did a three-year run on Cybill as the boozed-up Maryann Thorpe.
NOW: Baranski continued to thrive after Cruel Intentions, hooking parts on How the Grinch Stole Christmas (2000), Chicago (2002), Mamma Mia! (2008), Into the Woods (2014), and A Bad Moms Christmas (2017), as well as recurring roles on Happy Family, The Big Bang Theory, and The Good Wife. Since 2017, she has starred on the Good Wife spin-off The Good Fight, and in 2018 she reprised her Mamma Mia! role for the film’s sequel.
Tara Reid (Marci Greenbaum)
THEN: 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).
NOW: 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 the Zach Braff-starring Scrubs. She has starred in the Syfy franchise Sharknado since the series’ first installment in 2013.
Charlie O’Connell (Court Reynolds)
THEN: Charlie O’Connell played Kathryn’s ex-boyfriend Court Reynolds, the fuel behind her vindictive plot. Prior to Cruel Intentions, he most notably appeared in the sci-fi fantasy series Sliders as scientist Colin Mallory.
NOW: 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.
Herta Ware (Mrs. Sugarman)
THEN: 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).
NOW: Ware closed out her career with parts in Held Up (1999), Beautiful (2000), and Desperate But Not Serious (2000). She died at the age of 88 in 2005.