Billy Crystal’s Next Chapter

The beloved comedian looks back on his acclaimed career and previews his upcoming projects for stage and screen.

WORDS Jeanne Wolf
March / April 2020

Photo by Getty Images

I’ve gone to places I never thought I would and met some of the best and the greatest. I’m grateful for every second of my ride. Sometimes you make your own luck and sometimes it’s a twist of fate, like the one that started my friendship with Muhammad Ali.

I was a substitute schoolteacher starting out in stand-up. My best bit was an interview between Howard Cosell and Ali—I did both parts. There was a dinner honoring Ali right after he upset George Foreman. Robert Klein was supposed to perform but he had to cancel. Dick Schaap called my agent looking for a replacement. The agent said, “I’ve got this new kid who does an impersonation of Ali. He’d be perfect.” Suddenly, there I was sitting on the dais. They asked, “How should we introduce you? You have no credits.” I went, “Just say I’m one of Ali’s closest and dearest friends.” You can imagine the look on the champ’s face when he heard that. Anyway, my bit was a hit. Afterward, Ali hugged me and whispered in my ear, “You’re my little brother.” That’s what he called me for four decades as we became very close. “It’s really hard what you do,” he once said to me, “making people laugh.” I answered, “They say stand-up is the toughest thing.” Ali looked at me and said, “Have you ever been hit by Joe Frazier?”

Then there’s Robin Williams. Robin’s mind flew so fast and in so many different ways, which is what made him funny. He was such a presence for years. You needed a hit of him on The Tonight Show or Letterman. It was medication we all needed for the world’s ills.

Shout! Studios

Our phone calls were like jazz concerts. We were both insomniacs and we would talk into the night. I was watching Ronald Reagan’s funeral on TV and the phone rang. It was Robin doing Reagan and I said, “I’m watching your funeral.” He goes, “Well, that’s not me. That’s my stuntman. He took one for the team. But I want you to know I’m in heaven.” And I said, “What’s heaven like?” “Well, it’s a lot hotter than I thought it was going to be.”

Robin was my other brother, like Ali. But I don’t put myself in their class. They were fearless and always fighting for the best, not just for themselves but also the world.

Robert De Niro became one of my dearest friends after we did Analyze This together. I remember we had a very short scene on the first day. He came in looking like he needed a makeover and a couple hours later he stepped on the set shining. So we did this little bit and he was great. When we finished he said, “I want to talk to you.” I was petrified, thinking I’d screwed it up. De Niro said, “I want you to help me be funny. Anytime you can do that please let me know.” The funniest thing he did was cry during our therapy scenes. He didn’t need any help from me. 

With Carole Kane in The Princess Bride

Other actresses were auditioning for the female lead in When Harry Met Sally…. Meg Ryan came in and we didn’t even read. We just sort of giggled together. We kind of fell into each other. It was like when I met my wife, Janice. I just knew Meg was right for the role. When Rob Reiner and I went to an audience screening for the first time we were a little nervous. Meg’s climax scene in the deli came on the screen and Rob and I just looked at each other. Everybody went wild.

Rob directed me in When Harry Met Sally…, and also This Is Spinal Tap and The Princess Bride. I played his best friend in one episode of All in the Family. Afterward we said, “Let’s keep doing this. Let’s keep being best friends.” When we moved to Hollywood from New York, Rob and Penny Marshall really took us under their wing. I’m very proud of what Rob has done, especially politically.

My wife, Janice, and I will be married 50 years in June. We make each other laugh and that’s always been such an important part of our lives together. I met her when I was 18. We’ve been through everything, all the ups and downs, and the middle. Don’t forget the middle. We still learn from each other.

With Meg Ryan in When Harry Met Sally... (1989)

We have differences but we celebrate them. People talk about love at first sight between Sally and Harry. That was me with Janice and I’m still sighting.

My new movie is Standing Up, Falling Down, with Ben Schwartz. I play a lonely guy whose son hates him so much he won’t let him see his grandchildren. Ben plays a struggling comic. I help him and he helps me fill the void in my life. We’re both trying to come to terms with past mistakes. My character looks back on his missteps and goes, “Regret, that is real.” Funny enough, although I’ve had regrets, I’ve never dwelled on them. I think of what the baseball great Satchel Paige said: “Don’t look back. Something may be gaining on you.”

This fall you can see me with Tiffany Haddish in Here Today. I play a comedy writer who’s in the beginning stages of Alzheimer’s. The plot sounds dramatic but it’s really funny. Tiffany plays a singer who performs in the subway and we make a connection. Our sensibilities are great together. The characters have a love for each other that’s not romantic but even deeper. She’s a bigger-than-life talent and to harness that in the best way was our challenge together. There are very emotional moments that she hasn’t played in films.

I loved celebrating movies when I hosted the Oscars and I loved trying to do different things that nobody had done before. I mean, who else would have sat on Clint Eastwood’s lap in the audience when he was nominated for Mystic River and sang him a song?

Hosting the Academy Awards, 2012

I feel like I’m doing some of my best work. We’ve been working on bringing Mr. Saturday Night to Broadway, taking what was beautiful about the movie and transferring it to the stage. It’s close to happening. It’s not a big, splashy musical because my character is a Willy Loman with laughs. He’s one of those performers who needs that little extra hug you get from strangers. But although I love it, I don’t need it. What I really love is just being out there, which is why I’m so grateful for the long affair I’ve had with audiences.

At this age, to have a chapter three with two movies and maybe a Broadway show is great. There’s a creative burst happening like when I first started out. Everyone’s saying, “Why aren’t you slowing down?” I say, “For what?” I got friendly with George Burns. I said, “George, would you ever retire?” And he said, “I still love putting on my tux, walking out there, singing my songs and telling jokes. What would I do?” So that drives me. I want to do good work with honesty and humanity.


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