The pair reunited earlier this year for a Super Bowl commercial to celebrate the 35th anniversary of the film, which was written by the late Nora Ephron
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Billy Crystal and Meg Ryan reunited to present the biggest prize of the night at the 2025 Academy Awards!
The When Harry Met Sally costars had a surprise reunion at the Oscars, held at the Dolby Theater in Los Angeles on Sunday, Mar. 2, when they presented the award for Best Picture to Anora.
The pair walked out on the stage to the popular song “It Had to Be You” — which was featured in the hit 1989 film — before launching in a comedic exchange teasing Crystal’s numerous Oscar hosting gigs. (The actor notably hosted the Academy Awards in 1990, 1991, 1992, 1993, 1997, 1998, 2000, 2004 and 2012.)
“It’s great to be back, because, you know, I used to work here,” Crystal, 76, teased, to which Ryan, 63, responded, “You did? When was the first time?”
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“Nine tuxedos ago,” the comedian said. “Actually, my first time hosting it was 35 years ago this month. Yeah, I know it’s weird. It’s weird because on my IMDb page, I’m 47.”
The pair then “cut to the chase,” so to speak, as Crystal dropped an Oscar-worthy version of his iconic line from When Harry Met Sally: “Because when you have a chance to be an Oscar winner for the rest of your life, you want the rest of your life to start as soon as possible.”
The You’ve Got Mail actress attended the award show in a strapless red-wine-colored velvet gown with matching platform heels. She completed the look with blushed cheeks and a glossy berry lip, while rocking her signature crimped hairstyle.
As for the Saturday Night Live alum, he donned a classic black suit with a matching black bow tie. He also had his reading glasses ready to announce the Best Picture winner.
This isn’t the first time the pair have reunited this year. The two were featured in a Super Bowl commercial for Hellmann’s, where they recreated their iconic fake orgasm scene at New York City’s Katz’s Deli. Crystal told PEOPLE the timing was right to revisit the beloved movie, written by the late Nora Ephron.
“It was our 35th anniversary of the film, and it’s the first time that we’ve been offered something like that,” he said of the commercial. “It was a really fun idea, and the approach was right.”
“They were so respectful of the movie and of the scene too,” Ryan added to PEOPLE of Hellmann’s. “They came to us with just an enormous amount of respect for that, for the source material and for the characters.”
The original movie was directed by Rob Reiner, and also starred the late Carrie Fisher as Sally’s best friend Marie and the late Bruno Kirby as Harry’s best friend Jess. Both Crystal and Ryan received Golden Globe nominations for the movie, and Ephron’s screenplay was nominated for an Oscar.
