Reese Witherspoon, Ryan Phillippe’s Ups and Downs Over the Years
Sarah Hearon
Reese Witherspoon and Ryan Phillippe called it quits in 2006 after seven years of marriage — a timeline
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Us Weekly
Credit: Jim Smeal/BEI/Shutterstock

Reese Witherspoon and Ryan Phillippe’s Ups and Downs Over the Years

Once one of Hollywood’s most beloved couples, Reese Witherspoon and Ryan Phillippe called it quits in 2006 after seven years of marriage — but the twosome are forever linked thanks to their look-alike children. While many believe that the twosome met and fell in love while filming the 1999 movie Cruel Intentions, Witherspoon confirmed on Watch What Happens Live With Andy Cohen in 2015 that they had been “living together for about a year and a half” when they shot the film. She also told Andy Cohen at the time that daughter Ava and son Deacon hadn’t seen the movie. “They’re like, ‘This is so weird!’ And especially seeing me and their dad having sex. It’s so weird,” she said at the time. “Not interested.” Phillippe, meanwhile, recalled telling their kids about making the movie during a 2014 HuffPost Live interview. “It was funny — we were reminiscing then because we shot a lot of Cruel Intentions [in New York City], so there we were with Ava and Deacon talking, and they were tripping out on the fact that we were there shooting a movie before they were even a thought in our minds,” he said, noting that the former spouses were in a “really great place” at the time. “It’s a feeling-out process. … It’s going well, and she’s happy and remarried, and our kids are incredible. I’m proud of the way we’ve handled it and who our little people are.” [sendtonews type="float" key="KCy18WjqFM-3118745-14453"] It wasn’t always smooth sailing for the twosome, however. When news of their split broke in 2006, Phillippe was accused of cheating on Witherspoon with Stop-Loss costar Abbie Cornish. "I'm not a perfect person, but I'm not guilty of a lot of the things I have been accused of. My priority is and always has been the health and safety of my family," he said in a statement in November 2006. Phillippe and Cornish went on to date until February 2010. He later welcomed a daughter with then-girlfriend Alexis Knapp in 2011. Witherspoon, for her part, married talent agent Jim Toth and gave birth to son Tennessee in September 2012. Witherspoon and Toth announced in March 2023 that they were divorcing after nearly 12 years of marriage. In 2014, the Big Little Lies star recalled how her split from Phillippe — which came months after she won her first Oscar — affected her career. "Phew, that was a tough year that followed. I got divorced the next year and I spent a few years just trying to feel better,” Witherspoon said on 60 Minutes. “You know, you can't really be very creative when you feel like your brain is scrambled eggs. I was just kind of floundering career-wise cause I wasn't making things I was passionate about, I was just kinda working. It was really clear the audiences weren't responding to anything I was putting out there." Scroll through for a timeline of Witherspoon and Phillippe’s ups and downs:

Credit: Jim Smeal/BEI/Shutterstock

Reese Witherspoon and Ryan Phillippe’s Ups and Downs Over the Years

Once one of Hollywood’s most beloved couples, Reese Witherspoon and Ryan Phillippe called it quits in 2006 after seven years of marriage — but the twosome are forever linked thanks to their look-alike children. While many believe that the twosome met and fell in love while filming the 1999 movie Cruel Intentions, Witherspoon confirmed on Watch What Happens Live With Andy Cohen in 2015 that they had been “living together for about a year and a half” when they shot the film. She also told Andy Cohen at the time that daughter Ava and son Deacon hadn’t seen the movie. “They’re like, ‘This is so weird!’ And especially seeing me and their dad having sex. It’s so weird,” she said at the time. “Not interested.” Phillippe, meanwhile, recalled telling their kids about making the movie during a 2014 HuffPost Live interview. “It was funny — we were reminiscing then because we shot a lot of Cruel Intentions [in New York City], so there we were with Ava and Deacon talking, and they were tripping out on the fact that we were there shooting a movie before they were even a thought in our minds,” he said, noting that the former spouses were in a “really great place” at the time. “It’s a feeling-out process. … It’s going well, and she’s happy and remarried, and our kids are incredible. I’m proud of the way we’ve handled it and who our little people are.” [sendtonews type="float" key="KCy18WjqFM-3118745-14453"] It wasn’t always smooth sailing for the twosome, however. When news of their split broke in 2006, Phillippe was accused of cheating on Witherspoon with Stop-Loss costar Abbie Cornish. "I'm not a perfect person, but I'm not guilty of a lot of the things I have been accused of. My priority is and always has been the health and safety of my family," he said in a statement in November 2006. Phillippe and Cornish went on to date until February 2010. He later welcomed a daughter with then-girlfriend Alexis Knapp in 2011. Witherspoon, for her part, married talent agent Jim Toth and gave birth to son Tennessee in September 2012. Witherspoon and Toth announced in March 2023 that they were divorcing after nearly 12 years of marriage. In 2014, the Big Little Lies star recalled how her split from Phillippe — which came months after she won her first Oscar — affected her career. "Phew, that was a tough year that followed. I got divorced the next year and I spent a few years just trying to feel better,” Witherspoon said on 60 Minutes. “You know, you can't really be very creative when you feel like your brain is scrambled eggs. I was just kind of floundering career-wise cause I wasn't making things I was passionate about, I was just kinda working. It was really clear the audiences weren't responding to anything I was putting out there." Scroll through for a timeline of Witherspoon and Phillippe’s ups and downs:

Credit: Peter Brooker/Shutterstock

March 2002

The pair made headlines when Phillippe addressed their pay disparity while presenting with Witherspoon at the 74th Academy Awards.

“You make more than I do. Go ahead,” the actor replied after his then-wife asked if she could read the winner.

Nearly two decades later, Witherspoon admitted she was “flummoxed” by the remark.

“I forgot that ever happened. He did say that, and no, it wasn’t scripted. He didn’t tell me he was going to say that before it happened on air,” she explained on the “HFPA in Conversation” podcast.

The Legally Blonde star went on to share a story about Ava being “so embarrassed” in 2nd grade by a classmate discussing her mother’s success.

“I said, ‘Don’t ever feel ashamed of a woman making money.’ There are women all over this world who don’t have an opportunity or an education or the ability to make money,” she recalled. “The more women who make more money will give more money away, will take care of their societies, will take care of their communities, will do more with that money.”

Credit: Matt Baron/BEI/Shutterstock

2010

Phillippe and Cornish called it quits in February 2010. He later went off about their headline-making romance and split on Howard Stern that April.

"I have a new rule: not to date anyone who has a publicist. Who announces a breakup? I don't understand that! There's no need for that,” he said. "I've been dumped on in the press for relationship stuff since Reese and I divorced. I'm tired of getting s—t on. I don't feel like I deserve it. Things happen! How many people have you broken up with over your life?"

Phillippe also revealed that Witherspoon reached out to him after his split from Cornish — and he did the same after she split from Jake Gyllenhaal.

“It’s gotten to a place where we're great friends and great coparents,” he said.

Credit: Steve Eichner/WWD/Shutterstock

April 2013

Witherspoon made headlines in April 2013 after she was arrested for a count of disorderly conduct for interfering with police as Toth was booked for a DUI.

“I clearly had one drink too many and I am deeply embarrassed about the things I said," she told Us in a statement at the time. "It was definitely a scary situation and I was frightened for my husband, but that is no excuse. I was disrespectful to the officer who was just doing his job. The words I used that night definitely do not reflect who I am. I have nothing but respect for the police and I'm very sorry for my behavior."

A source told Us at the time, "Ryan doesn't care what she does. It's about the kids.”

Toth was sentenced to community service, one year of probation and an alcohol education program after pleading guilty, while Witherspoon pleaded no contest to disorderly conduct and was ordered to pay a fine.