Ryan Phillippe Shares Throwback Pic of Him and Ex-Wife Reese Witherspoon When They Were 'Hot'
Entertainment Tonight News Reese Witherspoon Ryan Phillippe
Sophie Schillaci
Ryan Phillippe and Reese Witherspoon were married from 1999 to 2008 and share two children, Ava and Deacon.
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Entertainment Tonight
Ryan Phillippe must have been taking a walk down memory lane. The 49-year-old actor shared a throwback photo with ex-wife Reese Witherspoon on social media, looking back on what he calls "a cooler time."

The Prey star took to his Instagram Story on Monday to post an image from the 2001 Hamptons premiere of Legally Blonde. In the shot, the then-married couple rocks edgy striped looks. Witherspoon wears her hair cropped short, while Phillippe's is styled in a mohawk.

"We were hot and drenched in late '90s angst," he captioned the pic, tagging 48-year-old Witherspoon.

"Such a cooler time than today," he added.

It wasn't all brooding looks for the photogenic couple. More photos from the event show Witherspoon and Phillippe happily flashing smiles for the cameras, as well.

Phillippe's post comes on the heels of Witherspoon's announcement that there's a Legally Blonde prequel series currently in development from her Hello Sunshine production company. Elle, which has been picked up by Prime Video, will focus on a younger version of Witherspoon's beloved Elle Woods character as she navigates high school.

Earlier this year, both Witherspoon and Phillippe celebrated the 25th anniversary of their iconic teen drama, Cruel Intentions.

The risqué film -- a modern retelling of Pierre Choderlos de Laclos' 1782 novel Les Liaisons dangereuses -- was a major hit upon its release in 1999, and remains popular to this day.

Cruel Intentions also notably marked the beginning of Witherspoon and Phillippe's real-life romance. The pair tied the knot just a few months after the film's release, but divorced in 2008. They share two children, daughter Ava Phillippe, 24, and son Deacon Phillippe, 20.

Witherspoon went on to wed Jim Toth in 2011 and welcome another son, Tennessee, 11. Witherspoon and Toth split in 2023 after 12 years of marriage.

The Big Little Lies actress later opened up to Harper's Bazaar about her decision to announce the news of her divorce with Toth via a joint statement on Instagram -- a stark contrast to how her divorce from Phillippe had been handled in 2008.

"It’s interesting what happened to me," Witherspoon told the outlet. "When I was divorced before, the tabloid media got to tell people how I was feeling or how I was processing, and it felt very out of control."

She continued, "To be able to talk to people directly about what’s going on in my life and just share it in the way that I share great professional experiences or personal experiences, it feels much more authentic to be able to say things in my own voice and not let somebody else control what’s happening. Then, of course, there’s speculation, but I can't control that."

For his part, Phillippe later welcomed another daughter, Kailani, 12, with his ex-girlfriend, Pitch Perfect actress Alexis Knapp.

Witherspoon and Phillippe's eldest children, Ava and Deacon, have been making their own way in the entertainment world recently.

The proud parents reunited just last year to support Deacon at the release party for his album, A New Earth. Around that time, Phillippe opened up to ET about his kids' futures.

"The focus is really music, that's what he's in school for right now," Phillippe said of his son. "He may dabble in acting at some point but he's got a great album about to come out, and he's looking at signing with a label soon. So, that's going to be his focus."

As for Ava, he said she's "undecided" about acting, but added, "You never know what'll happen in the future."

More recently, Ava stepped out as a brand ambassador for the brand Vince Camuto.

Witherspoon, meanwhile, had son Deacon on her arm at the 2024 Golden Globes Awards in January.

"He makes me really proud," the actress told ET of attending the awards show with her son. "He's a genuinely curious, intelligent young guy and we're just so excited to get a little time to spend together."