If you were around in 1999, Cruel Intentions likely made its way onto your radar. What began as a modest independent project quickly transformed into a teen drama blockbuster, capturing the attention of a wide audience upon its release in March 1999.
An adaptation of the 1782 French novel Les Liaisons dangereuses (Dangerous Liaisons), the film was brilliantly reimagined by screenwriter and director Roger Kumble, who shifted the story to focus on the lives of privileged American teenagers.
While the storyline was compelling, it was the star-studded ensemble cast that truly drew teenagers to theaters, turning Cruel Intentions into a cultural phenomenon and cementing its status as a cult classic.
Reese Witherspoon and her boyfriend Ryan Phillippe attend the ‘Cruel Intentions’ Westwood Premiere on February 25, 1999, at Mann Village Theatre in Westwood, California (Credit: Featureflash Photo Agency / Shutterstock)
Helmed by (now instantly recognizable) names like Reese Witherspoon, Sarah Michelle Gellar, Ryan Phillippe, and Selma Blair, Cruel Intentions received mixed reviews when it premiered. However, the performances of the young cast members caused the film to gain a cult level of appreciation that is still felt today.
We’re sure the storyline filled with drama, sex, and seduction definitely didn’t hurt, however. The People v. O. J. Simpson: American Crime Story actress Selma Blair, who starred as Cecile Caldwell in the movie, was 26 years old when the film was released on March 5, 1999. She celebrated her 27th birthday on June 23, 1999.
Selma Blair attends the ‘Cruel Intentions’ Westwood Premiere on February 25, 1999, at Mann Village Theatre in Westwood, California (Credit: Featureflash Photo Agency / Shutterstock)
In this article, we’ll look at the major stars of Cruel Intentions and how old they were when the film first premiered. Let’s dive in.
1. Sarah Michelle Gellar: The Age and Role of Kathryn Merteuil
Sarah Michelle Gellar was born in April 1977 in Long Island, New York. Gellar had a childhood interest in figure skating and even earned a black belt in taekwondo.
However, these interests were forced to fall by the wayside as Gellar began her acting career at a young age upon being spotted by an agent at a restaurant in Upper Manhattan.
Gellar first appeared in television commercials at age 4, notably a controversial Burger King commercial that caused her to be banned from McDonald’s in a subsequent lawsuit.
Sarah Michelle Gellar dazzles in a daring black dress with sheer panels at the Cruel Intentions Westwood premiere on February 25, 1999 (Credit: Featureflash Photo Agency / Shutterstock)
As a child actress in the early 1980s, she landed smaller roles in a variety of films and starred in the long-running soap opera All My Children in 1993. Her character premiered to much fanfare, although Gellar would leave the show only two years later to explore other opportunities.
It’s a good idea that she did because she was then cast as the eponymous character in Buffy the Vampire Slayer in 1997, a wildly popular television show created by famous showrunner and film director Joss Whedon.
The short actress followed up this famous role with roles in popular drama films like I Know What You Did Last Summer (1997) and horror films like Scream 2 (1997).
When Cruel Intentions was released in 1999, she was 21 years old, and she celebrated her 22nd birthday on April 14, 1999.
Sarah Michelle Gellar as Kathryn Merteuil in the 1999 American teen romantic drama film Cruel Intentions (Credit: Sony Pictures Releasing)
Gellar stars in the film as Kathryn Merteuil, a manipulative, vindictive, popular, and beautiful high schooler who seeks to destroy people’s lives for her own sick amusement and desire for revenge.
We’re sure that Gellar’s fame as a star in summer teen dramas and a popular television show attracted the casting directors and persuaded them to give her the lead role.
2. Reese Witherspoon: How Old She Was as Annette Hargrove
Hailing from New Orleans, Louisiana, and born in 1976, Reese Witherspoon began her acting career when she auditioned for a bit role in the 1991 film The Man in the Moon.
Much to her surprise, the then 15-year-old Witherspoon landed the lead role of Dani Trant, a young girl who falls in love for the first time.
She followed up this early breakthrough success with lead roles in films like Disney’s A Far Off Place (1993) and S.F.W. (1994), which further helped to solidify her status as a talented young actress with plenty of promise.
However, the film that gained her the most notoriety at this stage in her career was Freeway (1996), a black comedy in which she starred as Vanessa Lutz, a poor, illiterate girl who runs into a serial killer while trying to travel across the country.
Reese Witherspoon keeps it simple and chic in a white dress with a vibrant orange ribbon at the Cruel Intentions Westwood premiere on February 25, 1999 (Credit: Featureflash Photo Agency / Shutterstock)
The film received positive reviews from critics at the time (with Witherspoon’s performance getting specific admiration, although it was a failure at the box office. Witherspoon was 20 years old when she appeared in the film.
1998 was a busy year for Witherspoon, as he landed lead roles in three films: Overnight Delivery, Pleasantville, and Twilight. Despite positive reviews for her performance in Pleasantville, none of the films were box-office successes.
By 1999, Witherspoon was a reasonably established young star with plenty of experience, although she had failed to star in many successful box office films.
Reese Witherspoon and Ryan Phillippe hold hands as they arrive together at the Cruel Intentions Westwood premiere on February 25, 1999 (Credit: Startraksphoto)
While Cruel Intentions was in pre-production, Witherspoon was dating her co-star Ryan Phillippe, who plays Sebastian Valmont. They met for the first time at her 21st birthday party in 1997 and married shortly after the film was released.
“I don’t know what came over me — maybe the seven Midori sours — but I told [Ryan], ‘I think you’re my birthday present,’” she told Jane magazine in 1998. “He thought it was so flattering, and now that I think about it … how embarrassing!”
Reese Witherspoon and Ryan Phillippe share a tender moment in a scene from Cruel Intentions, where they played the characters Annette Hargrove and Sebastian Valmont (Credit: Sony Pictures Releasing)
Philippe convinced Witherspoon to take on the role of Anette Hargrove over a dinner date. “I thought we were all just going to dinner as friends, and then Roger and Ryan asked me to do the movie,” she said.
“I remember a lot of coercing.” – recalls Witherspoon. Luckily, Witherspoon took on the role, as Cruel Intentions was a box-office success, and her role as the innocent and naïve Hargrove is still admired today.
When Reese Witherspoon filmed Cruel Intentions during the summer of 1998, she was 22. She celebrated her 23rd birthday on March 22, 1999.
3. Ryan Phillippe: Age and Portrayal of Sebastian Valmont
Unlike many young Hollywood stars, Ryan Philippe came from humble beginnings and was born in Delaware in 1974.
After signing with a management agency in New Jersey, Philippe got his first taste of acting by playing the recurring role of Billy Douglas in the daytime drama One Life to Live from 1992 to 1993.
After appearing in various minor roles in multiple television shows and films, Phillippe hit his big breakthrough by appearing in I Know What You Did Last Summer (1997) when he was 23.
Sarah Michelle Gellar and Ryan Phillippe exude chemistry as Kathryn Merteuil and Sebastian Valmont in a pivotal scene from Cruel Intentions (Credit: Sony Pictures Releasing)
I Know What You Did Last Summer was a massive box office success, helping to solidify Philippe’s status as a sex symbol for teenagers in the late 90s and reignite the slasher genre for the era (along with Scream, another popular entry into the genre).
Philippe followed up this breakthrough performance with another starring role in the film 54, which followed the story of the famous Studio 54 nightclub in New York City.
Ryan Phillippe was 24 years old when she attended the premiere of Cruel Intentions in 1999 (Credit: Featureflash Photo Agency / Shutterstock)
The film was a modest financial success but did not fare well with critics then. In 1999, Philippe was cast in Cruel Intentions in the lead role of Sebastian Valmont, undoubtedly due to his status as an actor who could portray sexy male characters to a tee.
Philippe was 24 years old when he starred in Cruel Intentions, making him the oldest of the three main protagonists in the film. He celebrated his 25th birthday on September 10, 1999.
His character is perhaps the most interesting one in the film. Although he starts out as a scheming womanizer, in the end, he genuinely falls in love with Witherspoon’s character, Hargrove.
1999 American teen romantic drama film Cruel Intentions starring Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair (Credit: Sony Pictures Releasing)
Decades after its initial release, Cruel Intentions still attracts a respectable level of fanfare and discussion, which is a testament to its popularity and the performances of the main cast. Even after two mediocre sequels, many still have fond memories of the original film and the original cast that made it truly special.