The Celebrity Who Has Hosted The Oscars The Most Times

Despite the recent and devastating wildfires in Southern California, the show must go on. In this case, the show is nothing short of the biggest night in Hollywood: the Academy Awards. The 2025 Oscars ceremony will take place on March 2 and is welcoming a brand-new host to the proceedings. That host is the lanky, red-haired ex-late-night host Conan O’Brien, who is no doubt going to have a tough task ahead of him. Hosting the Oscars is something that’s fraught with peril, as many of its past hosts can attest, from movie stars like James Franco and Anne Hathaway (remember the year when they hosted?) to multi-talented performers like Neil Patrick Harris and Hugh Jackman and even late-night hosts like Jimmy Kimmel. O’Brien has to be playful with his jokes, but not too playful as to make it seem like he’s savaging filmmakers or actors (especially in light of the wildfires). He also has to make sure his comedy isn’t too edgy or offbeat, so as to not alienate the massive audience (some of whom may, shockingly, not be familiar with his style of humor). On top of all that, he has to follow in the footsteps of legends as well.

If you’re from Generation X or the Millennial era, you may think of one person when you think of the consummate Oscars host: Billy Crystal. Although he was a common presence at the Oscars throughout the 1990s, he actually doesn’t even come within shouting distance of the celebrity who hosted or co-hosted the Oscars the most times in their history of televised ceremonies. The standard-bearer is one of the most legendary performers of all time: comedian Bob Hope, who served as emcee no less than 19 times over the course of 26 years. Looking back at the history of Oscars hosts is a fascinating little time capsule in and of itself, but even though Hope’s last hosting effort came in 1978, he’s still the top of the mountain and no one’s close to topping him.

In many ways, Bob Hope set the standard for what an Oscars host should be like, both for the audience of A-Listers in the room as well as the vast audience watching around the world. There’s the monologue at the outset, along with playful ribbing of the various films and performers up for awards. Hope was also guaranteed to make a handful of jokes about the length of the ceremony itself (a bit that has arguably become a bit more tired over time), at the same time managing to never feel like he was being too nasty or mean to anyone involved. Certainly not every future host got that memo, such as when Seth McFarlane hosted in 2013 and performed a song about the various women who have disrobed to show off their naked bodies in previous roles. But Hope managed to establish what an overall awards-show host should be by his continued hosting of the Oscars through the advent of television in the 1950s, 1960s, and 1970s.

For the younger generations, though, it was Billy Crystal (who has hosted the show nine times across a few decades) who took the baton from Hope creatively and expanded it. More modern hosts, including O’Brien when he’s hosted the Emmys, like to do riffs on the nominated efforts themselves, sometimes inserting themselves into actual clips. And that really started with Crystal, partly because the technology may not have existed when Hope was hosting the Oscars decades before. If O’Brien’s own awards-show history is any evidence, he may eschew that specific gag. When he hosted the Emmys in 2006, though he did pop up in the worlds of shows like “Lost,” “House,” and “The Office,” it wasn’t as if he appeared in pre-existing scenes; instead, he filmed new bits with the actors from those shows on their respective sets. The truest indication may come from another bit he did at the same Emmys featuring a different iconic comedian named Bob — namely, when he trotted out Bob Newhart in an enclosed glass box and said that if the show didn’t end by a certain time, Newhart would die because of the limited amount of air in the box. It’s edgier than the material Hope worked with back in the day, but still feels like a natural growth of similar comedy.

In any case, the most obvious question to ask when you think about Bob Hope and his 19-time hosting efforts at the Oscars is this: can anyone hope (ahem) to top his record? Is anyone even close to doing so? Crystal remains the closest contender, but he’s also hosted less than half as many times and is older now than Hope was when he stopped hosting the annual ceremony. The next person on the list would be multi-hyphenate Whoopi Goldberg, who’s hosted four times (and is almost 70 herself). The aforementioned Jimmy Kimmel has hosted just three times, and it’s only because he chose not to host this year (due to the workload along with his late-night show on ABC) that O’Brien is stepping in. (And as much as Conan is one of the great comedians of his generation, and hopefully kills it at the Oscars, he’s older than 60 himself.) So, the short answer to the question is probably not — the only person who might even seem like a logical fit as Oscars host is someone who hasn’t done it before: comedian John Mulaney, who has been memorable as a presenter as well as the emcee of last year’s AMPAS Governors’ Awards. But you can’t begin to reach Hope’s heights without hosting yourself.

So, for now, and for a while, Hope’s record as a 19-time host of the Oscars seems safe from competitors. Although younger generations may not have much awareness of the consummate comedian (outside, perhaps, of his appearance in “The Muppet Movie” as a sly ice-cream vendor), Hope is pretty much one of the most iconic performers whose influence has spanned decades, from his TV specials to his film work to his constant presence as a friendly, if sharply funny, emcee. Perhaps Conan will do well enough that he returns (and unlike Kimmel, he no longer has a late-night show to take up his time on a weekly basis), but even still, he’ll have a long way to go before he can top Hope as the most frequent Oscars host.