Ryan Phillippe: Living in the shadow of Reese Witherspoon

An incestuous pair of siblings, an innocent virgin, a phenomenal soundtrack, a cunnilingus scene and true love: It’s hardly surprising that “Cruel Intentions” hit pop culture like a bomb at the end of the 1990s. It was Ryan Phillippe (50) who, as the blond, curly-haired Sebastian Valmont, drove therapists, women and girls crazy and gave the female audience hope that true love could bring any bad boy to his senses.

The first gay teenage role in the USA

Before Ryan became the duckface of the Gen X/Millennial generation, the boy, born in 1974 in New Castle, Deleware, was hardworking. His mother had found him an agent when he was just 13 years old. Since then, he has been auditioning for commercials and TV roles. This was the case in 1992, when he got the role of Billy Douglas in the American soap opera “One Life to Live”. Billy Douglas is considered the first openly gay teenager in a TV series. The role broke a taboo at the height of the AIDS crisis in the USA and was a risk for the young actor. The young Phillippe said of his decision at the time: “I thought: ‘What will my family think? What about my friends?’ But I realized that the pain for Billy is a hundred times greater.”

A few supporting and television roles later, Phillippe played alongside Sarah Michelle Gellar (47), Jennifer Love Hewitt (45) and Freddie Prinze Jr. (48) in the 1997 teen horror film “I Know What You Did Last Summer”. Phillippe finally became a global teen heartthrob in 1999 with “Cruel Intentions”. In the romantic thriller, the initially ruthless womanizer Valmont finds true love. The reason for this is the role of Reese Witherspoon (48), who also turned Phillippe’s head in real life.

Young screen love with Reese Witherspoon

During the filming of Cruel Intentions, the film couple were either already together – or fell in love in real time. The two had met about a year earlier on Witherspoon’s 21st birthday. In the same year that the film was released, they married at the ages of just 23 and 25. Daughter Ava Phillippe (25) was born six months later. She was followed in 2003 by son Deacon Phillippe (20). But the young love did not last forever. In October 2006, Phillippe and Witherspoon announced the end of their marriage.

There was speculation in the media that Phillippe no longer wanted to be in the shadow of his wife, who had won the first Oscar for “Best Actress” in 2006. Phillippe’s look at the award ceremony did not actually show much joy. But there had already been tension at the Oscars four years earlier. At that time, the couple were supposed to read out the nominations for best makeup. Witherspoon jokingly asked her husband if she could open the envelope. He replied snippily: “You make more money than I do. Go ahead.” An unspoken comment that Witherspoon later said had “irritated” her.

“I don’t want to be seen like that”

After the end of his marriage, Phillippe revealed in an interview with “W Magazine” that the divorce was “the darkest and saddest place I’ve ever been.” He said he didn’t get out of bed for four to five months, and because of the paparazzi he didn’t want to leave the house. The interest of the photographers, “because I was married to the highest-paid actress in the world,” bothered him. He continued: “I don’t want to be seen like that.”

Sooner or later, he inevitably had to make peace with the situation. After all, escaping from Hollywood didn’t help him either. Because he wanted distance, Phillippe flew far away after the divorce, but was also approached there shortly after landing, as he reported to the Guardian in 2022. However, this time with the question: “Excuse me, are you Justin Timberlake?”

His career also continued after “Cruel Intentions”, although never as steeply as that of his ex-wife: In the neo-western “The Way of the Gun” he played alongside Benicio del Toro (57) and Juliette Lewis (51) in 2000. In the three-time Oscar-winning episodic drama “LA Crash” he was seen alongside Sandra Bullock (60) and Matt Dillon (60) in 2004. In 2006 he played the leading role in the war film “Flags of Our Fathers” by Clint Eastwood (94), in 2010 he was seen in the drama “The Bang Bang Club”, in 2007 in the action thriller “Unmasked – Treason at the Highest Level” and in 2011 alongside Matthew McConaughey (54) in the legal thriller “The Client”.

Serious accusations from ex-girlfriends

Phillippe never remarried, but has a daughter with his ex-girlfriend Alexis Knapp (35), with whom he dated briefly in 2010. He was later engaged to Paulina Slagter, a law student at the time, who filed a harassment complaint against him in 2017 but dropped it shortly afterwards. A similar story happened with another ex-girlfriend, Elsie Hewitt (28). She accused him in the same year of hitting her and throwing her down a flight of stairs. Phillippe firmly denied all allegations and the lawsuit was settled.

He is still busy today: In 2024, the horror comedy “Saint Clare” will be released, in which Phillippe can be seen alongside Bella Thorne (26), as well as the action thriller “Prey”, in which he plays the leading role alongside Mena Suvari (45). Nevertheless, one should not expect to see a wrinkled Phillippe on the screen in the coming decades. “Out of vanity, I am not enthusiastic about the idea of ​​aging on screen,” he explained in an interview with the “Guardian”. A sentence that could also have come from Sebastian Valmont.