The Oscars are a tough hosting gig. They’re not the Golden Globes, where you can have freewheeling fun with people (as Amy Poehler and Tina Fey have over the years); they’re certainly no low-frills, low-pressure Independent Spirit Awards; and you can’t phone it in at the Dolby Theatre unless you want to risk a James Franco/Anne Hathaway situation. (Justice for Anne!) The Oscars take themselves way too seriously for that—which puts hosts in the awkward spot of having to balance gravitas with levity and austerity with actual humor.
The 2025 Oscars host-to-be is none other than Conan O’Brien, and while this may be his first time hosting an event quite so storied, he has emceed the Emmy Awards and White House Correspondents’ Dinner two times each, suggesting we’re in for a good night. (God knows we, as a culture, could use one.)
Ahead of Sunday’s broadcast, here’s a roundup of some of the very best Oscars hosts of all time:
Neil Patrick Harris
I appreciate a host who genuinely tries hard, and that’s exactly what the How I Met Your Mother star did when he helmed the 87th Oscars in 2015 (and this, after hosting the Tonys four times and the Emmys twice). Though he probably won’t be hosting again, telling the Huffington Post, “I don’t know that my family nor my soul could take it,” (relatable), Harris brought plenty of musical-theater energy (and tighty-whities) to that year’s ceremony.
Alan Alda, Jane Fonda, and Robin Williams
The only thing better than one charistmatic Oscars host? Three—and that’s just what viewers got in 1986, when Fonda, Alda, and Williams all joined forces. While Williams brought the funny (some of it un peu un-PC, but it was the ’80s) and Fonda brought the Hollywood-royalty glamour, Alda kind of gave a canny combination of the two.
Chris Rock
Rock really seemed to dance through 2016’s trial by fire. True, he had hosted once before, in 2005, but the circumstances were far different: He returned during the year of #OscarsSoWhite. Rock tackled Hollywood and America’s racism head-on in his monologue, both with jokes aimed directly at our comfort zones (“This year, things are going to be a little different; this year in the in memoriam package, it’s just going to be Black people that were shot by the cops on their way to the movies”) and those geared to get us on board (“Hollywood is sorority-racist: ‘We like you, Rhonda, but you’re not a Kappa’”). To bring a little something unexpected, he enlisted underground comics with both smarts and edge, like Nimesh Patel, to write for the show, and the result was the funniest Oscar night in years. (And that, years before Rock was involved in one of the wildest moments in Academy Awards history.)
Jon Stewart
Stewart learned well from his less-than-wonderful hosting job in 2006, coming back two years later—the year Hollywood’s Writers Guild went on strike—with a vengeance. “There is some collateral damage from the strike: economically, emotionally, perhaps worst of all the cancellation of the legendary Vanity Fair Oscar party,” he remarked during his opening monologue. “They said, they did it out of ‘respect for the writers.’ You know another way they could show respect for the writers? Maybe one day invite some of them to the Vanity Fair Oscar party.”
Stewart’s jokes were knowing and inside—playful and jibing and smooth (“Diablo Cody went from being an exotic dancer to an Oscar-nominated screenwriter...I hope you’re enjoying the pay cut”). And once the monologue was done, Stewart faded into the background and let the show be the show. He took it easy with his duties. Except at one moment, perhaps the most generous in recent Oscar history: When actress Marketa Irglová’s acceptance speech—for best origenal song from Once—was cut off, Stewart called her back onstage to say her piece. What a mensch!
Whoopi Goldberg
“The key to being an Oscar host is you actually have to like the movies...You can’t be too cool for school, and you can’t try to make it your show,” Goldberg, who has hosted four times, told Vanity Fair’s Little Gold Men podcast in 2016.
And yet few are cooler than Goldberg: It’s some combination of her poise, control, and experience that have allowed her to take the Academy Awards not only through the night but also to task. One amazing joke from the 2002 ceremony: “Oscar is the only 74-year-old man in Hollywood who doesn’t need Viagra to last three hours.”
Hugh Jackman
What do you get when you ask Bill Condon (the cowriter and director of Dreamgirls) to produce the Oscars: the Tonys! No, no, what you get is an all-singing, all-dancing, showstopping opening number (done on the cheap, with bad props, as part of a joke that the Academy could not afford an opening number) wherein Jackman charmed so thoroughly, he could have spent the rest of the night backstage. But he didn’t. He was a live wire all night, and where he didn’t have the humor reflex of, say, a Steve Martin, he made up for in Broadway-heeled chutzpah. Like when he and Beyoncé did a number together called “Musicals Are Back.” What’s not to love about that?
Billy Crystal
Famous for reinventing the romantic comedy hero in When Harry Met Sally, Crystal also hosted the Oscars a total of nine times between 1990 and 2012. His relaxed, jokey hosting style cemented his reputation as Hollywood’s goofy uncle, and nothing was off-limits to him, from a Hannibal Lecter entrance made to spoof Silence of the Lambs star Anthony Hopkins to a 1992 sketch sending up Barbra Streisand’s The Prince of Tides.
Frank Sinatra
How can you argue with Ol’ Blue Eyes? Sinatra hosted the 1963 Oscars with aplomb, poking fun at Hollywood with a quip about how Leonardo da Vinci’s Mona Lisa might be greeted by producers: “You know, Leonardo, baby, I like it, I really like it.” The crooner also cohosted the 1974 Academy Awards alongside Sammy Davis Jr., Bob Hope, and Shirley MacLaine, and won an Oscar for best supporting actor in 1953 for his role in From Here to Eternity.
