Billy Crystal and Meg Ryan Reunite at His Broadway Show, 37 Years After When Harry Met Sally

The beloved When Harry Met Sally… costars reunited on Tuesday, Nov. 3, when Ryan stopped by New York City’s Imperial Theatre to see Crystal in his new Broadway show, 860.

Crystal, 78, shared a photo of the two posing together after the performance, celebrating the visit with a sweet nod to their longtime friendship.

“An old friend stopped by the Imperial last night,” he wrote on Instagram.

The reunion marks the latest get-together for the stars of the beloved 1989 romantic comedy, who have shared the spotlight several times in recent years.

Most recently, the pair appeared together at the 97th Academy Awards in March 2025, when they presented the Best Picture Oscar to Anora. Walking onto the stage to “It Had to Be You,” a song famously featured in their movie, they delighted audiences with a playful exchange that included Crystal revisiting one of Harry Burns’ most memorable lines.

“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,” he joked, putting an Academy Awards spin on Harry’s romantic declaration from the film.

Just weeks earlier, Ryan and Crystal recreated the film’s iconic Katz’s Deli scene for a Hellmann’s Super Bowl commercial. The ad featured Ryan once again demonstrating Sally Albright’s famously enthusiastic reaction to a sandwich, with Sydney Sweeney making a cameo to deliver the immortal punchline, “I’ll have what she’s having.”

At the time, Crystal told PEOPLE that returning to the beloved characters more than 35 years after the film’s release felt surprisingly natural. “It felt the same,” he said of sitting across from Ryan at the famed New York City deli.

Their enduring chemistry has long been part of the movie’s appeal. In a 2024 interview with PEOPLE, Crystal reflected on what made their onscreen partnership so special.

“You knew it was special,” he said. “You don’t know that it’s 35 years special.”

More recently, Crystal revisited the making of When Harry Met Sally… in PEOPLE’s October 2026 cover story, revealing that he wasn’t director Rob Reiner’s first choice to play Harry Burns. “I said, if he wants me, then he wants me, but I know he’s seeing other people,” Crystal recalled of waiting for his longtime friend to offer him the role.

When Reiner finally called, Crystal remembered, the director told him, “I always knew it was you.”

The comedian also shared how his real-life friendship with Reiner helped shape some of the movie’s most beloved moments. One scene, in which Harry and Sally watch Casablanca together over the phone, was inspired by the pair’s own late-night conversations.

“That was stuff we did,” Crystal told PEOPLE. “That was pure us.”

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Reiner, who died alongside his wife, Michele, in December 2025, remained one of Crystal’s closest friends for decades. Their relationship also plays an important role in 860, which Ryan attended this week.

The deeply personal one-man show, which opened Oct. 21, takes its name from the street address of the Los Angeles home Crystal shared with his wife, Janice, for 46 years. Through hilarious Hollywood anecdotes, family memories and reflections on friendship, the production explores how the comedian has coped with losing the house in the January 2025 Pacific Palisades wildfires.

In his October 2026 PEOPLE cover interview, Crystal revealed that creating the show became an important part of his healing process. “It wasn’t just, ‘Oh, I’m going to make a play out of this,’ “ he explained. “No, it was healing me at the same time.”

The production also carries a special connection to Reiner, who encouraged Crystal to turn his experiences into a Broadway show and even helped settle on its title. “I think 860. That’s the one. I love that,” Crystal recalled his friend telling him.

For Crystal, the production is ultimately about finding a way forward through life’s most difficult moments, with the help of the people who matter most.

“Laughter made my life possible,” he told

Tickets for 860, which is scheduled to run through Jan. 3, 2027, are on sale now.