The Fascinating Journey of the 'Cruel Intentions' Cast: Catch up with Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and More

Long Island iced tea, please! Even after two decades since its release in 1999, Cruel Intentions continues to captivate fans with its scandalous plot and the irresistible charm of its lead character, Sebastian Valmont.

This iconic 90s cult classic, inspired by the French film Dangerous Liaisons, revolves around the intriguing relationship between Sebastian (played by Ryan Phillippe) and his alluring stepsister Kathryn Merteuil (portrayed by Sarah Michelle Gellar). Kathryn daringly challenges Sebastian to seduce the innocent Annette Hargrove (played by Reese Witherspoon), the daughter of their school's new headmaster, setting the stage for a thrilling tale of manipulation and desire.

Sebastian is taken by surprise when he falls in love with Annette and experiences heartbreak after she discovers the truth about the bet. Ultimately, Annette emerges victorious, outplaying Kathryn in her own game, and rides off into the sunset. Unfortunately, Sebastian is not by her side as he sacrifices himself to save Annette. However, as she drives his cherished convertible, she feels his presence while The Verve's "Bittersweet Symphony" plays in the background.

Talking exclusively to We in September 2021, Phillippe shared, "It brings a smile to my face almost every time. It doesn't matter where I am. There have been instances in my life where I'm at a gas station or somewhere similar, and suddenly I hear the song playing from a distance. Then a group of people would start waving at me. It's like they deliberately played the song because they spotted me there."

The actor from The Big Sky, who became engaged to Witherspoon during the filming of the drama, expressed his thoughts on being associated with a particular song. He acknowledged that there are far worse songs to be linked with and praised it as a truly great song. Whenever he hears the opening strings, it still brings him joy and puts a smile on his face. (Phillippe and Witherspoon got married in 1999 but ended their marriage seven years later.)

Cruel Intentions not only revolves around the twisted love story of Sebastian and Annette, but also sheds light on the hidden lives of a group of students attending an elite prep school on the Upper East Side. This includes their sexual encounters, mischievous behavior, and scandalous extracurricular escapades.

Kathryn's manipulation of Cecile Caldwell becomes particularly memorable in one iconic scene where she uses her as a pawn in her game, teaching her how to kiss. Additionally, Cecile's motivation stems from wanting to impress her music teacher, leading her to seek guidance. When asked about Selma Blair's kissing skills, Gellar praised her, emphasizing the softness of her lips and her pleasant scent.

The actress from Buffy the Vampire Slayer revealed that kissing a girl on camera is preferable because it avoids the issue of makeup rubbing off, which requires touch-ups when kissing a guy. Reflecting on her past, the actress from I Know What You Did Last Summer admitted that while she anticipated the film would be iconic, she was unaware of the extent of its success.

"And I was instantly captivated when I read the script, filled with an overwhelming desire to be a part of it," expressed Gellar. "It has held a special place in my heart for as long as I can remember, having witnessed every rendition and Broadway adaptation."

Credit: Bob Frame/Columbia/Kobal/Shutterstock

Long Island iced tea, please! Even after two decades since its release in 1999, Cruel Intentions continues to captivate audiences with its scandalous plot and the irresistible charm of its protagonist, Sebastian Valmont.

In the 1990s cult classic, a teenage adaptation of the French film Dangerous Liaisons, Sebastian's stepsister Kathryn Merteuil presents him with a provocative challenge: to seduce the daughter of the new school headmaster, Annette Hargrove. Little does Sebastian know, he will unexpectedly fall in love with Annette and be left shattered when she discovers the truth behind their bet. Ultimately, Annette emerges triumphant, outsmarting Kathryn at her own game, and rides off into the sunset. Unfortunately, Sebastian is unable to join her as he sacrifices himself to save Annette. However, as she drives his cherished convertible, she can still feel his presence, accompanied by the heartfelt tune of The Verve's "Bittersweet Symphony" playing in the background.

Phillippe shared with We in September 2021 his fondness for the final scene playlist, which never fails to bring a smile to his face. He recounted instances where he unexpectedly heard the song playing at a gas station, only to discover a group of people waving at him, knowing he was there. These encounters reaffirmed the impact of the song on his life.

Despite the association with the song, Phillippe expressed his gratitude that it is a great song to be connected with. He emphasized that whenever he hears the opening strings, it still brings him joy and puts a smile on his face. This pleasant association serves as a reminder of the positive memories tied to the song. (Phillippe and Witherspoon got married in 1999 but ended their relationship after seven years.)

Cruel Intentions not only delved into the twisted love story of Sebastian and Annette but also shed light on the clandestine lives of a clique of privileged prep school students from the Upper East Side. The show explored their sexual escapades, mischievous endeavors, and scandalous extracurricular adventures.

A particularly memorable moment occurred when Kathryn cunningly used Cecile Caldwell (played by Selma Blair) as a pawn in her game, teaching her how to kiss. Cecile sought Kathryn's guidance to impress her music teacher (portrayed by Sean Patrick Thomas).

Gellar praised Selma's kissing skills, describing her as a fantastic kisser. She emphasized the softness of Selma's lips and complimented her pleasant fragrance. The Buffy the Vampire Slayer actress admitted that kissing a girl on camera is a preferable experience compared to kissing a guy. She explained that when kissing a guy, the makeup tends to rub off, requiring frequent touch-ups. However, when kissing a girl, there is no such concern, making the experience more convenient.

The actress, known for her role in I Know What You Did Last Summer, shared with Us that she had a feeling the film would become "iconic," although she couldn't anticipate its level of success. Gellar expressed her strong desire to be involved in the project after reading the script, stating that she has been a devoted fan of the story for a long time, having watched every version, including those on Broadway.

Scroll down to see what the cast of Cruel Intentions has been up to since 1999:

Credit: Shutterstock (2)

Sarah Michelle Gellar

Gellar's portrayal of the conniving Kathryn Merteuil in the cult classic came two years into her role as Buffy Summers on Buffy the Vampire Slayer. Following the end of the TV series in 2003 after seven seasons, she went on to appear in movies such as the Scooby-Doo franchise, The Grudge, Possession, and in 2016, she reprised her role as Kathryn in the Cruel Intentions TV movie. In addition to her film work, Gellar has also made appearances on various television shows including The Ringer, The Crazy Ones, Star Wars: Rebels, and Masters of the Universe: Revelation. She served as an executive producer on The Ringer and has been involved in numerous other projects. In 2015, Gellar cofounded the baking kits startup Foodstirs and later released the Stirring Up Fun With Food cookbook.

In her personal life, Gellar tied the knot with her co-star Freddie Prinze Jr. in 2002. Together, they have two children: daughter Charlotte and son Rocky.

Credit: Shutterstock (2)

Phillippe portrayed the role of Sebastian Valmont, Kathryn's mischievous stepbrother, in the movie. He also appeared in several other films such as Company Man, Crash, Breach, MacGruber, The Lincoln Lawyer, Brothers by Blood, and One Shot. Additionally, he showcased his acting skills in television shows like Damages, Secrets and Lies, Shooter, Big Sky, and MacGruber. In 2014, Phillippe ventured into writing and directing with his debut film, Catch Hell. He not only wrote and directed the project but also took on the role of a producer. Since then, he has continued to serve as a producer on Shooter and The 2nd.

The actor tied the knot with his Cruel Intentions costar, Witherspoon, in June 1999. They were blessed with a daughter named Ava and a son named Deacon before going their separate ways in October 2006. Additionally, the actor is a father to another daughter named Kai, whom he shares with his ex-partner, Alexis Knapp.

Credit: Shutterstock (2)

Reese Witherspoon

Witherspoon played the role of Annette Hargrove, the daughter of the headmaster, who eventually develops feelings for Sebastian. The actress, who hails from Louisiana, has appeared in various films such as Election, American Psycho, Legally Blonde, Sweet Home Alabama, Walk the Line, Water for Elephants, Wild, Home Again, A Wrinkle in Time, and voiced the character of Rosita in the Sing franchise. In addition to her successful film career, Witherspoon has also found success on television with hits like Big Little Lies, Little Fires Everywhere, and The Morning Show. With over 30 producing credits to her name, she has been involved in projects such as Legally Blonde 2: Red White & Blonde and TV series True Be Told and The Morning Show.

Apart from her acting career, the star of Just Like Heaven launched her own company, Draper James, in 2015. A year later, she co-founded the media company Hello Sunshine. In 2017, Witherspoon started Reese's Book Club and the following year she published her book, Whiskey in a Teacup. Fans of the Legally Blonde franchise will be delighted to know that Witherspoon is set to reprise her iconic role as Elle Woods in the highly anticipated Legally Blonde 3 film.

The actress from "Pleasantville" was formerly married to Phillippe for the period of 1999 to 2006. Together, they have a daughter named Ava and a son named Deacon. Witherspoon tied the knot with Jim Toth in 2011 and one year later, they welcomed their son, Tennessee. Unfortunately, the couple announced their separation in March 2023, just two days before their 12th wedding anniversary.

Credit: Shutterstock (2)

Selma Blair

The actress portrayed wealthy teenager Cecile Caldwell, who becomes involved with Sebastian before acquiring some skills from Kathryn. Blair then starred in Zoe, Duncan, Jack & Jane before reuniting with Witherspoon for Legally Blonde. She has since made appearances in The Sweetest Thing, the Hellboy franchise, In Their Skin, Mothers and Daughters, and After We Collided. Blair has also appeared on various TV shows such as Anger Management, Heathers, and Another Life.

In 2018, the Kath & Kim alum announced that she had been diagnosed with multiple sclerosis. She released a memoir titled Mean Baby: A Memoir of Growing Up in May 2022, where she extensively shared her experiences with health challenges.

The Michigan-born individual was previously wedded to Ahmet Zappa from 2004 to 2006, and subsequently had a two-year relationship with Mikey Day. In 2010, Blair started a new chapter with Jason Bleick, and a year later, the couple joyfully welcomed their son Arthur into the world. Unfortunately, the pair decided to part ways in 2012.

Credit: Shutterstock (2)

Joshua Jackson

Jackson portrayed the character of Blaine Tuttle in the movie, who acts as Sebastian's friend and partner in crime. Blaine manipulates Annette's former boyfriend into sleeping with him and then uses this information to blackmail him. During this time, Jackson was also known for his role as Pacey Witter on the television series Dawson's Creek, which was on air between 1996 and 2003. Later on, he appeared as Peter Bishop in Fringe, Cole Lockhart in The Affair, Bill Richardson in Little Fires Everywhere, and Dr. Christopher Duntsch in Dr. Death. In addition to his television work, Jackson has also been a part of various films such as Cursed, Shutter, Inescapable, Sky, and Braddock, which is set to release in 2022.

Prior to his relationship with Jodie Turner-Smith, Jackson had a decade-long romance with Diane Kruger, which ended in 2016. He eventually found love again and tied the knot with Jodie in December 2019. The couple welcomed their first child, a daughter, in April 2020.

Credit: Shutterstock (2)

Eric Mabius

The actor played the role of Greg McConnell, a football player who Sebastian and Blaine suspect may have informed Annette about Sebastian's true intentions. Originally from Pennsylvania, he also appeared in movies such as Tempted, Resident Evil, A Christmas Wedding, and Where the Road Meets the Sun. Mabius is best known for his portrayal of Oliver O'Toole in the Hallmark Movies & Mysteries franchise Signed, Sealed, Delivered, both in the film series and the corresponding television show. He has also appeared in various other TV shows including The O.C., Eyes, The L Word, Ugly Betty, Outcasts, and Chicago Fire. In 2018, Mabius made his debut as a producer with the film Welcome to Christmas.

The Reading Writing & Romance actor has been married to Ivy Sherman since 2006. They share sons Maxfield and Rylan.

Credit: Shutterstock (2)

Sean Patrick Thomas

Thomas' Ronald Clifford was Cecile's music instructor and later became her romantic partner. He has also appeared in various films such as Save the Last Dance, Halloween: Resurrection, Barbershop, The Fountain, The Murder Pact, Christmas Hotel, Influence, The Tragedy of Macbeth, and Trophy Wife. Additionally, he has made appearances on television shows such as The District, Reaper, Ringer, Vixen, For All Mankind, and Reasonable Doubt.

In 2006, the native of Washington, D.C. and University of Virginia graduate, tied the knot with Aonika Laurent. Together, they have a daughter named Lola and a son named Luc.

Credit: YouTube; Picture Perfect/Shutterstock

Louise Fletcher

Fletcher took on the role of Helen Rosemund, Sebastian's aunt, in the film. She then went on to showcase her talent in several other movies such as The Contract, Touched by a Killer, Manna from Heaven, Finding Home, A Perfect Man, and Grizzly II: Revenge. Additionally, the Academy Award winner made appearances in popular TV shows including Star Trek: Deep Space Nine, ER, Heroes, and Shameless.

The One Flew Over the Cuckoo’s Nest star was married to film producer Jerry Bick from 1959 to 1978. The actress and her late ex-husband share sons John and Andrew.

Credit: Shutterstock (2)

Christine Baranski

Baranski portrayed the role of Bunny Caldwell, Cecile's strict mother, in the Broadway production. She has also appeared in various other films and shows such as How the Grinch Stole Christmas, Chicago, Bonneville, Mamma Mia!, Into the Woods, A Bad Moms Christmas, and Christmas on the Square. In addition to her acting career, Baranski has worked as a producer on The Good Fight and has contributed to more than 20 entertainment soundtracks. She has been involved in theater productions like Sweeney Todd, Mame, and Follies. Baranski was married to actor Matthew Cowles for 31 years until his passing in 2014, and they have two daughters named Isabel and Lily.

Credit: Shutterstock (2)

Tara Reid

Reid took on the role of Marci Greenbaum, the daughter of Sebastian's therapist. Originally from New Jersey, she later gained recognition for her performances in popular films such as the American Pie series, Josie and the Pussycats, Van Wilder, Unnatural Causes, Charlie's Farm, and the Sharknado franchise. In addition to her acting career, Reid made her producing debut with the film 7-10 Split in 2007 and has since worked as an executive producer on over 15 films. She has also made appearances on various reality shows, including Celebrity Big Brother, Big Brother's Bit on the Side, and Marriage Boot Camp: Reality Stars.

Credit: Shutterstock (2)

Charlie O’Connell

O’Connell made his debut as Kathryn’s ex-boyfriend Court Reynolds in his first major film. He then went on to star in a series of movies including Dude, Where’s My Car?, Kiss the Bride, Unlucky Charms, Mischief Night, and Staged Killer. The actor, known for his role in Sliders and the younger brother of Jerry O’Connell, also took on the role of the lead in the fifth season of The Bachelor, which aired in 2005.

After splitting from his Bachelor winner, Sarah Brice, in 2010, the New York native moved on with Anna Sophia Berglund whom he wed in 2018.