What Billy Crystal Knew About Hosting the Oscars

When I started watching the Oscars as a child in 1998, Billy Crystal’s presence felt as fundamental as the Oscar statue itself. Did I understand the jokes, such as when he sang about Titanic to the Gilligan’s Island theme? No way—but Crystal’s smirking tone and raised brows suggested we were all in on it. His unseriousness not only cut through the competitive tension of the night, but also acted as a kind of safety tether for his fellow movie actors: No matter how rude he got, Crystal was roasting Hollywood from the inside. He knew, better than many hosts since, that entertaining the audience outside the room depended on the energy of the stars inside it.

As the Oscars have fought for simultaneous memeable relevancy (remember Ellen’s selfie?) and artful prestige in the past two decades or so, the exact role the host should play has been unclear. Should they be clever-funny? Slapstick? Mean? Reverent? Without direction, the outcome has been chaotic: one-off hosts, two awkward hosts who don’t like each other, three hosts, no host whatsoever. I don’t understand this ongoing identity crisis. Though Crystal hasn’t graced the Oscars stage in a dozen years, his tenure illustrated the almost-ideal emcee: aware of the pressures of the industry, familiar with the films, friendly with the nominees, easygoing enough not to let a bad joke faze him and keen enough to know how to land a really good one. Perhaps today’s awards-show producers fear that Crystal’s style of old-fashioned showmanship would make the Oscars feel dated. I regret to tell them: The Oscars are already a vestige of a bygone era of Hollywood. Why not lean into it? A little song and dance never hurt anyone.

Crystal’s first monologue in 1990 was characteristic—apparent nervousness aside—of how he’d host the Oscars in years to come. “There are 300 feature films in that five-minute montage,” he said of the preshow segment, “and what’s amazing is that according to Paramount, not one has yet to go into profit.” Paramount—and the obscene wealth of Hollywood in general—was a frequent punch line for him, invoking, perhaps, the initial purpose of the Academy Awards themselves when they were started, in the late 1920s.

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The early impetus for the Oscars was twofold: They reminded actors, directors, and writers that what they did was fun and important. They were also meant to keep the artists from organizing in an era of Hollywood labor disputes—solidarity was much more difficult when prizes were offered. The Oscars, Crystal explained during his most recent turn as host, in 2012, “celebrate a Hollywood tradition that not only creates memories for the ages but also breeds resentments that last a lifetime.” Though Crystal didn’t spell it all the way out, history shows that those grudges can range from the professional (Netflix versus the traditional studios) to the personal (actors making seemingly passive-aggressive comments about one another), stemming from the competitive nature of the awards. (That’s part of why it feels so disingenuous to hear winners thank their fellow nominees—for what, losing?) In short, the Academy Awards’ ability to divide and conquer worked for a number of years.

Recent hosts have reflected this division with a kind of a free-for-all negativity. Jimmy Kimmel seemed to have an air of smug distaste, while Seth MacFarlane went in a cruder direction with his “We Saw Your Boobs” song about female actors’ on-screen nudity. And the Amy Schumer, Wanda Sykes, and Regina Hall trifecta stumbled through inconsistent chemistry as they, too, attempted to insult their peers. Hall set up a joke about how the coronavirus pandemic had been difficult for people, which Schumer followed with, “Just look at Timothée Chalamet!” as the camera cut to the older J. K. Simmons. These ad hominem attacks were essentially irrelevant to the awards, snuck in only for the sake of a lazy gag.

Crystal’s jokes about the stars could still be remarkably misguided: His use of blackface to imitate Sammy Davis Jr. in 2012 was particularly distasteful. But his primary target every year was the Academy itself. He doubled down on the absurd grandiosity of the contest. At his first Oscars, in 1990, he joked, “Six months ago, who would have possibly thought that the Berlin Wall would come down, that Nelson Mandela would be freed,” to rapturous applause, before adding, “and most incredibly, Meryl Streep would not be nominated for an Academy Award.” Crystal showed that, despite all of the Academy Awards’ viewers and pageantry, nominations and snubs meant little to those outside of that room.

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His jokes could take on the Oscars even more directly. “It’s great to be back here at the show,” Crystal said in 1997, “or as it’s known this year, Sundance by the Sea.” The oddest difference, according to him, was that in years past, “the major studios were nominated for Oscars.” This play on the studios’ increasing out-of-touchness (especially during the stodgy ’90s era when they favored trite melodramas) takes a swing at the industry, not any particular person. Few people have a greater public platform to call out those who make Hollywood’s business decisions. Simply put, Crystal punched up. What helped him get away with the jabs, beyond being a consummate showman, was that he clearly understood and held an appreciation for movies. Recent Oscars hosts such as Chris Rock and Neil Patrick Harris have done their turns on the big screen, but at the time when Crystal was hosting, he had spent most years, if not every other year, since the late 1970s making a movie.

This undercurrent of respect for the form, combined with Crystal’s dramatic skills, is perhaps best represented in his Oscars medleys, in which he skims through all the Best Picture nominees in a jokey musical number. He’s done one every year that he’s hosted, asking the audience, “You didn’t think I wasn’t gonna do this, did ya?” back in 2012. The songs have an unrelenting goofiness that clearly lightens the mood in the ballroom. The Oscars aren’t that serious, he seems to convey: These are just movies, those are just actors. Their plots and performances can be turned into musical jokes, and who is the butt of the joke more than Crystal himself? Song medleys and montages have long been a part of the Oscars, but Crystal’s take on the tradition was doing a silly, almost bad-on-purpose iteration, one that made him look like the clown with his strained rhymes and forced lyricism. You can’t help but root for him.

Whether or not Crystal ever gives hosting another shot, his past performances offer clues to what could make the next emcees great. Embodying the gleeful showman requires a degree of humility, one that celebrities seem to be less and less inclined to express. But so much about the Academy Awards is ripe for comedy––the desperate campaigns, the misleading pull quotes, the unsubtle For Your Consideration billboards. When the host embraces the absurdity of the awards season, they can yield delightful results. Headlining the Oscars doesn’t have to be impossible—it just requires someone who loves what they do as much as they love making fun of it.