Ryan Phillippe has opened up about the raucous Academy Awards night he shared with Reese Witherspoon nearly two decades ago.
The actor, 50, appeared on “Live with Kelly and Mark” Wednesday and offered a rare glimpse into his marriage to the Oscar winner, now 48. Phillippe recalled the 2006 ceremony as a personal double-header: Witherspoon took home Best Actress for “Walk the Line” while his own film, “Crash,” claimed Best Picture.
“It was a wild night altogether because my wife at the time, Reese Witherspoon, also won Best Actress,” he said on the daytime talk show.
The evening delivered an unexpected celebrity encounter for Phillippe during the Best Picture announcement. Morgan Freeman presented the award, and the “Cruel Intentions” star found himself starstruck at the worst possible moment.
“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.”
The festivities stretched well past midnight. Phillippe remembered the couple partying “up until probably 5 or 6 in the morning” after the ceremony wrapped.
“We had such a fun after-party,” he gushed.
Witherspoon’s victory that night came for her portrayal of June Carter in the Johnny Cash biopic directed by James Mangold, with Joaquin Phoenix playing the country legend. “Crash,” directed by Paul Haggis, featured an ensemble cast including Sandra Bullock, Don Cheadle, Matt Dillon, Brendan Fraser, Terrence Howard, Thandiwe Newton and Ludacris, exploring racial and social tensions across Los Angeles.
The couple’s marriage, which had produced two children, was already approaching its end despite the glamorous Hollywood evening. Witherspoon filed for divorce months after the Oscars, and the pair finalized their separation in 2008.
During their seven-year marriage, the actors welcomed daughter Ava, now 27, in 1999 and son Deacon, now 22, in 2003. The exes have maintained an amicable co-parenting relationship in the years since, most recently appearing together at Deacon’s graduation from New York University this past May. Photographs from the event showed the former spouses smiling alongside their graduate son.
Phillippe’s comments mark a rare instance of the “Shooter” actor reflecting publicly on his high-profile marriage to the “Legally Blonde” star. Both have largely kept details of their relationship private since the divorce, with Witherspoon going on to marry talent agent Jim Toth in 2011 before announcing their divorce in 2023.