Ryan Phillippe Recalls 2006 Oscars Night with Reese Witherspoon

Ryan Phillippe still remembers the night he and Reese Witherspoon had Hollywood celebrating — and apparently, the party didn’t end when the Oscars did. The 9-1-1: Nashville actor, 52, revisited the unforgettable 2006 Academy Awards during recent episode of Live With Kelly and Mark. His film Crash won Best Picture just moments after Witherspoon took home Best Actress for Walk the Line, making it a huge night for the then-married couple. “It was a wild night altogether because my wife at the time, Reese Witherspoon, also won Best Actress,” Ryan shared. “While she was backstage giving her post-award interviews, they called Best Picture for Crash.” But Ryan’s biggest memory wasn’t just taking home an Oscar. It was meeting one of Hollywood’s legends — and getting a little starstruck. “Morgan Freeman was the presenter of the Best Picture and I had never met Morgan Freeman so I fanned out on stage at the Oscars,” he continued. “I’m like, ‘I’ve always wanted to meet you, sir,’ and this is while the producer is accepting the award. Kind of a funny moment.” “We had such a fun after-party,” he added, recalling that they partied “up until probably 5 or 6 in the morning.” Ryan and Reese divorced in 2008 but have continued co-parenting their children, Ava, 27, and Deacon, 22. The family reunited earlier this year to celebrate Deacon’s graduation from New York University. Ryan has also pushed back against criticism of celebrity children entering the entertainment industry. In a 2024 interview, he said Ava was still figuring out her career, while praising Deacon’s character and work ethic. “He makes me proud every single day of his life just in regards to the young man he’s become, to how he operates in the world,” he said of Deacon. “He’s just such a source of light and love, and he’s very solid and spiritual. He’s got an incredible work ethic.”