Reese Witherspoon Slapped Ryan Philippe in ‘Cruel Intentions’ After He Improvised off-Camera

Cruel Intentions is a film that still stands out as one of the all-time classic teen dramas. A 1999 movie that featured a star-studded cast, including Sarah Michelle Gellar, Ryan Phillippe, and Reese Witherspoon, Cruel Intentions received mixed critical reviews at the box office but was extremely well-received by fans. These days, viewers look to Cruel Intentions as a great example of the genre, as well as the film that united real-life couple Phillippe and Witherspoon. As it turns out, sparks flew between Phillippe and Witherspoon onscreen as well as off.

Why did Reese Witherspoon slap Ryan Phillippe in ‘Cruel Intentions’?

In Cruel Intentions, Ryan Phillippe played Sebastian Valmont, a privileged prep school student who prides himself on his skills as a womanizer and master manipulator. His plan to seduce the sweet Annette, played by Witherspoon, goes awry when he falls in love with her. Determined to protect her reputation, Sebastian lies to Annette, telling her that he never really had feelings for her – which led to a confrontation between the young couple.

The fight scene was full of intense emotions, and Phillippe was determined to get it right. According to a video on the MsMojo YouTube channel, Phillippe was improvising heavily during the scene, riling Witherspoon up to the point where she slapped Phillippe. The shocking moment was organic and raw, proving the characters’ pain – and director Roger Kumble decided to keep the take with the slap in the finished film.

How did Ryan Phillippe convince Reese Witherspoon to join the cast of ‘Cruel Intentions’?

While it might be difficult for fans to imagine anyone else in the role of Annette, Witherspoon was not initially drawn to the script for Cruel Intentions. In fact, during casting for the film, Witherspoon and Phillippe, who were dating at the time, had a number of discussions about the movie. Witherspoon would later recall that Phillippe tried hard to convince her that she was perfect for the character of Annette. In a 2019 oral history of the movie for Entertainment Weekly, Witherspoon noted that both Phillippe and Kumble pitched the movie to her during a dinner meeting. 

“I thought we were all just going to dinner as friends, and then Roger and Ryan asked me to do the movie,” Witherspoon said. “I remember a lot of coercing.” Phillippe added, “We drank a lot of wine. We were wooing her! She loved the movie for me, but it wasn’t a great part at the time for her. She helped Roger turn it into one.” The rest, of course, is history, with both Witherspoon and Phillippe signing on for Cruel Intentions and helping to make the film a cult classic.

Ryan Phillippe and Reese Witherspoon first met at a birthday party

Witherspoon and Phillippe had actually been dating for close to two years when they started filming Cruel Intentions. According to The List, the two first met at Witherspoon’s 21st birthday party, beginning their romantic relationship not long after. The two tied the knot in September 1999, and a few months after that, Witherspoon gave birth to their first child, a daughter named Ava. Four years after the arrival of their daughter, Witherspoon and Phillippe had a son named Deacon.

In 2006, seven years after they got married, Witherspoon and Phillippe announced their split. The two would later attribute their divorce to getting married at a very young age. After their divorce was finalized in 2007, Witherspoon and Phillippe went on to find love with other people. Still, they have remained good friends and continue to co-parent their two children amicably.