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Billy Crystal Just Wanted You to Love Him

The comic and veteran Oscar host’s best work capitalized on his incredible likability. But that need to please could sometimes be a curse

Welcome to Misleading Men, a regular feature where we look back at the actors who ruled Hollywood for one brief shining moment.

Tonight, Billy Crystal will be at the Tonys, where Mr. Saturday Night is up for five awards, including Best Musical. Crystal himself is nominated for Best Leading Actor in a Musical and Best Book of a Musical. There is a good chance the show (which opened on Broadway in April) will leave empty-handed — A Strange Loop and the revival of Company are going to be stiff competition — but the musical’s success and glowing reviews are probably compensation enough. And Crystal, who turned 74 in March, has reasons to be happy beyond possible awards: The show allowed his grandkids to see him on stage for the first time.

“That was the thrill of [it] all,” he said last month. “They’re 18, 16, 12 and 9. They’ve seen stuff over the years, you know, films and TV, but they never saw me live. … I so wanted them to be there, and they all flew in for it, and it was so emotional, thinking that they were in the audience.”

This is a very Billy Crystal thing to say. Other comics are edgy, trying to see how far over the line they can go. Meanwhile, he has been married to the same woman since 1970, his family the center of everything he does, his humor warm and cozy, inoffensive to the nth degree. Other stand-ups talk about killing on stage — he has spent his career wanting to give audiences a big hug. It’s a sensibility that’s hard to square with modern comedy, but there is one aspect of his personality that’s remained fascinating: his fanatical desire to get viewers to feel, which has sometimes doubled as a need to be loved and taken seriously. At the height of his film stardom, these impulses fueled his best work. But they’ve also slightly marred his legacy. A beloved institution, Crystal has been a household name for decades. But he’s also often seemed to want it a little too much.

Growing up on Long Island, he had a happy childhood. “We always had a house full of funny characters,” Crystal once said. “The relatives were hilarious. I started doing stand-up with my brothers; my mom had all the props. At school, I was always the class comedian — not the class clown. The class clown was the guy at graduation who hiked up his gown and had nothing on underneath. I was the class comedian, the guy who talked him into doing it.”

His dad died when Crystal was in his teens, the shock of it never leaving him. Their last conversation was a fight “about a girl, my first love,” he later said. “She had dumped me the week before: ‘I just want to be your friend.’ I was grief stricken. I had a chemistry test and couldn’t even open the book. Dad was mad at me. He said, ‘What are you doing?’ We got into it. I’d never been fresh with him my entire life — he was my idol — and I said something to him like ‘You don’t know what it’s like.’ He was pissed when he left to go bowling, and a couple hours later he was dead. The weight of it was horrible. … I got him all worked up, and he had a terrible heart attack.” 

Did Crystal really cause his father to have a heart attack? Probably not, but the guilt was palpable all the same, impacting how he would be as a father. As he put it, “[I]f I have a bad moment with my children, I can’t wait to say ‘I’m sorry.’”

Crystal went to NYU for film school, where Martin Scorsese was one of his teachers — “He was brilliant, scary,” Crystal recalled, “but with a love of movies that inspired anyone who was in those classes” — and became a stand-up, doing impressions and, eventually, starring on the ABC sitcom Soap, where he played one of TV’s first prominent gay characters, a director named Jodie. Launching in the late 1970s, Soap helped raise Crystal’s profile, but he soon grew sick of being shackled to a role that traded in negative stereotypes. “Billy was very forthright with it, that he was tired of this show,” his co-star Marla Pennington would say, later adding, “[T]his was like one of his first big breaks, and he was ready to move on. He was tired of playing the gay guy or whatever the jokes were; it was stale to him. He didn’t say it but you felt it, that he had other things to do. And he sure did.”

Crystal, who’d had a relationship with Saturday Night Live from its earliest days, joined the cast in the fall of 1984. (This was after having his own show, The Billy Crystal Comedy Hour, which ran for only five episodes. “I wanted to be edgier,” he recalled about the short-lived program, “and [NBC] wanted Carol Burnett, and there’s only one Carol Burnett.”) He was on SNL for one season before pivoting to a film career, starting with 1986’s buddy-cop comedy Running Scared, where he and Gregory Hines played Chicago police officers who crack wise. The script went through major changes before Crystal came on board. “Originally it was going to be Gene Hackman and, I think, Paul Newman playing … retiring cops,” Crystal said. “Then the script was just sort of sitting around and [director] Peter Hyams said, ‘I wanna go with these two guys, I think they’d be great together.’”

Running Scared’s moderate success opened the door for the following year’s bigger hits, The Princess Bride and Throw Momma From the Train, which showed off two sides of his persona. The former, a Gen-X staple, allowed him to do the over-the-top characterizations that were his speciality on SNL, whereas the Danny DeVito dark comedy demonstrated his ability to portray a harried regular guy — in this case, someone who inadvertently gets drawn into his writing student’s plan to pull off a Strangers on a Train-style double murder. Then in 1988, Crystal revealed his sentimental streak, co-writing and starring in Memories of Me, a mawkish comedy about a doctor (Crystal) who, after a heart attack, decides to patch up his relationship with his estranged father (Alan King). 

But 1989’s When Harry Met Sally was the breakthrough, a modern romantic comedy, written by Nora Ephron and directed by Rob Reiner, that reaffirmed New York City as the best place to fall in love (at least in movies) and gave the culture deathless bits like “Men and women can’t be friends” and “I’ll have what she’s having” — not to mention the revelation (for men) that women fake orgasms. 

“None of us had any idea what it would become,” Crystal told The Hollywood Reporter in 2019 about the movie. “I know it felt great. We had a great preproduction with all of us contributing to the script, and Nora was very open about taking suggestions and adding her magic to it. Rob was the best director I’ve ever worked with. He understood the human part of comedy and the rhythm of comedy. There’s no one like him. And we were able to create all these new things that weren’t in the script — together, all of us, including the orgasm scene.”

Even at the time, people noted that When Harry Met Sally was, essentially, a more polished Woody Allen rom-com, and in Crystal, who played cynical good guy Harry Burns, the film had a lovable everyman whose (mostly) platonic relationship with Sally (Meg Ryan) was hip and thoughtful. When Crystal got more famous, he would often steer toward the saccharine, but When Harry Met Sally held that tendency in check, resulting in his most touching performance — and also, according to Crystal, his invention of the term “white man’s overbite,” which decades later remains a societal symbol of a deeply dopey dude. 

As Harry, Crystal came to personify a new kind of man — vaguely cutting, actually pretty sensitive — that was funny but harmless, the sort who needed to grow up but wasn’t an overgrown kid, either. Crystal further refined the type with City Slickers, a broad but appealing fish-out-of-water/midlife-crisis comedy in which he and his fellow beta-male buddies decide to get their mojo back by going on a cattle drive, just their latest attempt to inject some excitement into their normie lives. It is, perhaps, the perfect film about dudes in their late 30s who are melancholy for no good reason, and City Slickers initially mocks their self-pity before taking it seriously, an indication of Crystal’s weakness for being a bit of a softie. Nonetheless, Jack Palance, a veteran of Westerns like Shane (the first film Crystal ever saw), who plays the no-bullshit leader of the cattle drive, won the Oscar, one of the rare instances where a comedy took home an acting prize. 

It’s hard to know if Oscars were part of the pull for Crystal’s new project, which adapted a character he’d first developed in the 1980s, making him the star of a sweeping comedy-drama about a self-sabotaging artist. But by the time of 1992’s Mr. Saturday Night, Crystal had already hosted the Oscars a couple times — not to mention the Grammys thrice — and had proved himself to be an ideal M.C. for such events. A smooth-running joke machine, middle-of-the-road but ingratiatingly cheerful, Crystal possessed an old-school professionalism back when awards ceremonies trafficked in such showbiz classiness. He’d go on to host the Academy Awards nine times, which is more than anyone other than Bob Hope, who did it 19 times. “I’d find myself getting defensive about it: ‘But I do other things,’” Crystal once said about his reputation for being, as he called it, the “designated host.” But he tried not to be too dismissive of the gig — or his ease in the role. “[I]t’s a weird ability [to do that job well],” he said. “If I enjoy it, why not do it more?”

Mr. Saturday Night, which was Crystal’s feature directorial debut, saw him fully embrace the pathos he’d often seeked in his work. Here was the tale of Buddy Young Jr., a Catskills comic who, for myriad reasons, was never as successful as he felt he should have been. Sometimes, it was just bad timing. (Going on Ed Sullivan’s show right after the Beatles guaranteed that nobody in America would remember his segment on the broadcast.) But, often, it’s just because he’s a son of a bitch, tormenting everyone in his life with his ego, jealousy and bitterness. 

As Buddy, Crystal seemed to be communicating something about himself — maybe that the dark flipside of his personality wasn’t that alien to him — but the movie’s maudlin tone reached for a dramatic grandeur that the script (co-written by Crystal) couldn’t deliver. Mr. Saturday Night was a classic example of a funnyman showing the sad clown underneath, striving for respect by being serious. It was hard not to see the Academy’s ignoring of the film — except for a sole Supporting Actor nomination for David Paymer, who plays Buddy’s long-suffering brother/agent — as a rejection of Crystal’s artistic aspirations.

To be sure, Crystal has received plenty of accolades. He’s won six Emmys, four for hosting or writing the Oscars. He’s been nominated for two Grammys. He received a Tony for his mid-2000s one-man show 700 Sundays. But when it comes to the Motion Picture Academy, it’s been noticeable how those around him have been honored (or, at the least, nominated) while he has not. Robin Williams and Whoopi Goldberg, his co-hosts on the popular annual charity comedy show Comic Relief, both took home Oscars. Palance won. Paymer got nominated. Meanwhile, he hosted the show, providing a steadying, reliable presence year after year. He was easy to take for granted, even if the shtick got predictable — another montage, another strained ad lib. 

Like other nice guys in Hollywood, Crystal has had trouble shaking the impression that he was “only” that. By comparison, his great friend Robin Williams was lauded as a tormented genius. Other funny nice guys, like Tom Hanks, managed to convey the gravitas necessary to be respected as significant actors. Crystal played the gravedigger in Kenneth Branagh’s opulent Hamlet, he sneakily portrayed a soullessly successful author in Woody Allen’s caustic Deconstructing Henry and he had hits with Analyze This and Monsters, Inc. But he rarely demonstrated the ability (or desire) to surprise. He wasn’t interested in “challenging” an audience — he just wanted to make them laugh. “[Comedy] was always serious for me,” he told Oprah Winfrey. “I can’t do much else.”

But his pleasantly milquetoast demeanor has also left him feeling a bit like a lightweight — a tad one-dimensional. Film critic David Thomson probably put it as well as anyone when he wrote of Crystal, “There’s something in the cock of his head and the tightness of his eyes that cannot hide the knowledge that a laugh line is coming.” Or, even more damning, there was the 2001 episode of The Simpsons in which Marge makes a pretty lame joke, laughs at what she perceives to be her incredible cleverness and then comments approvingly, “I’m a regular Billy Crystal!” Bart’s withering response: “You got that right.” Popular and beloved he may be, but Crystal is probably cursed never to be cool.

Of course, a career like his argues against the value of coolness. As the Oscars have stumbled from one debacle after another in recent years, his bland, sturdy shows suddenly seem like the gold standard. (Even so, I have to point out that Steve Martin managed to be classy and witty in the gig — all the while conveying some edge. So it can be done.) But stand-up now attracts attention because of the inflammatory cruelty of the once-brilliant Dave Chappelle or the lethal craftsmanship of John Mulaney — to say nothing of the groundbreaking work of Hannah Gadsby or Jerrod Carmichael. There doesn’t seem to be much room for the smiling comfort of a Crystal. 

Perhaps that’s why for years he’s been working on turning Mr. Saturday Night into a musical, collaborating with screenwriters Lowell Ganz and Babaloo Mandel — who wrote City Slickers and co-wrote the Mr. Saturday Night screenplay with him — to get the show to Broadway. Revisiting Buddy Young, Jr. — and bringing back Paymer to once again play Buddy’s brother — Crystal is reconnecting with the bygone brand of comedy that once inspired him to get into the business, a mugging, proudly hokey style of joke-telling that wanted nothing more than to get you to laugh or groan.

In an interview with The Guardian in 2013, Crystal reminisced about his early influences. “My dad, Jack, had a great sense of humor and had a strong impact on me and my humor,” he said. “He prompted us to watch great comedians on television. The 1950s were a particularly great decade for television comics in the U.S. Dad had a music store, and he’d often bring home comedy albums that I would listen to. I started listening to Bob Newhart and Bill Cosby, and developing taste. They really influenced my style of comedy.” Crystal also acknowledged that, unlike other comics who started out as rabble-rousers, he’d been a good kid. “I didn’t rebel as a child,” he admitted. “I missed that angry teenager thing. I had a really great childhood. I always loved to get up and perform. I was the youngest of three, and the only thing I was moody about was that one brother is 6 feet, 2 inches and the other one is 5 feet, 10 inches. What happened to me?”

It’s the sort of self-deprecating line you expect from Crystal — eager to please, endearingly innocuous. Truth is, nothing happened to him — his legacy is secure, his happy life surrounded by his wife, children and grandkids firmly in place. “Our kids are adults and fulfilled in what they’re doing,” he said in 2004. “They need us in a different way, and we need them in a different way. And I think it’s all pretty great, because, as our folks used to say, it goes by so fast. So damn true. When it goes by and it’s good, it’s nice.” 

Perpetually uncool, he’s instead focused on happiness, a state of being he’s shared with a large audience who’s relished his aggressively agreeable work. Maybe even more than making people laugh, I suspect he loves to make them smile. That’s his great strength, but also something of a limitation. The best thing you can say about Billy Crystal is everybody likes him. And the worst thing you can say about him is everybody likes him fine enough.