How Jimmy Kimmel preps for the Oscars and why the end of his talk show may be near

The casts of "Moonlight" and "La La Land" all onstage with host Jimmy Kimmel and presenter Warren Beatty.
2017 Oscars host Jimmy Kimmel helps presenter Warren Beatty explain his mistake in announcing “La La Land” as the best picture winner when it was in fact “Moonlight.”
(Robert Gauthier / Los Angeles Times)

It’s 30 days before the Academy Awards, and Jimmy Kimmel is in a hotel in Las Vegas, the town where he grew up. The man who will host this year’s Oscars speaks to The Envelope by phone on the Friday before the Super Bowl, which is being held in Sin City. He’s thinking about how it all started for him.

“I’m looking out the window at my old neighborhood,” he says. “I think when I realized I got a charge out of hosting was, we had a big flea market at our church, and [our] priest, Father Bill, thought I was funny and asked me to be the emcee. I was about 15 years old — I got up on stage, and I was reading raffle numbers and making jokes, mostly making fun of Father Bill. People were really laughing, and I loved it.”

In the ensuing decades, the 56-year-old comedian has hosted everything from the American Music Awards to the Emmys — and, of course, there’s his talk show, “Jimmy Kimmel Live,” which just celebrated its 21st anniversary. The 96th Academy Awards on March 10 will be his fourth. His first, everyone remembers — it was the one that ended with the world briefly thinking “La La Land” had won best picture. That was 2017, and he was asked back the following year. After a few years off, Kimmel returned for the 2023 ceremony, the man responsible for reestablishing a sense of stability after the trauma and embarrassment of The Slap. Why did he agree to another go-round? Even he’s not sure.


“I did not think I would ever do it again,” Kimmel says. “I did two of them, and they went well — something crazy happened at one of them with a story I’ll have for the rest of my life. I know how much work goes into them, so I thought, ‘Yeah, I don’t necessarily want to do this ever again.’ ”

David Letterman sits in an armchair and leans in toward Jimmy Kimmel behind a desk on "Jimmy Kimmel Live."
Jimmy Kimmel finally got his idol, David Letterman, as a guest on “Jimmy Kimmel Live,” in 2012.
(Jeff Neira/ABC)

What changed his mind was “Top Gun: Maverick.” “I knew there was a movie that people had seen, and it just makes the job easier,” he explains. “Then this year, I am sitting in a movie theater watching ‘Barbie’ and thinking, ‘Well, maybe I’ll do this again, because at least I have a point of reference with everyone.’ ” Kimmel is experienced enough to know that the more popular the nominated films are, the more the audience in the Dolby Theatre will get references to a movie’s plot in his monologue. “I made a joke about ‘Moonlight’ that made it clear to me that the vast majority of the room had not seen the movie, even though it won best picture.”

In the Oscars’ nearly century-long history, only three people have hosted more times than Kimmel: Bob Hope (19), Billy Crystal (nine) and Johnny Carson (five). Kimmel is arguably the most unlikely member of that elite group, neither a Hollywood insider nor a generational icon. But he’s also a long way from the bro-friendly fare that first made his name, like his early-aughts Comedy Central series with Adam Carolla, “The Man Show,” refining his humor as he’s gotten older. Still, Kimmel seems to relish the juxtaposition of his unpretentious jocularity and the Oscars’ pomp and circumstance. As he puts it, “There’s an expectation that the show is going to be classy and pristine. I’m not always classy and pristine.”

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Performing came in many forms for Kimmel as a kid. He would watch Bill Cosby on “The Tonight Show,” writing out Cosby’s entire routine. He made crank calls. He was also an altar boy for seven years, although that was a lot more stressful. “It was just trying not to yawn with my mouth open, because my dad would yell at me.”


When Kimmel was approached about hosting the Oscars the first time, he knew he wasn’t the producers’ first choice, “which I was OK with — I understand it.” He didn’t have long to prepare — the invite came after Christmas, late by Oscar-hosting standards — but he was determined to kill. Maybe too determined — looking back, he feels he over-prepared for that first show. “I really rushed through my monologue,” he recalls. “I was nervous. But [afterward], I studied the tape and decided, ‘OK, I’m going to take my time with the monologue. I’m not going to race through it — if the show goes one minute long, I’m OK with that.’”

Does he fret about the jokes that have bombed on the show? Last year, he got criticized for a segment in which he surprised activist Malala Yousafzai, attending because she was nominated in the short documentary category, faux-seriously asking her if she thought that Harry Styles had really spit on Chris Pine during the Venice premiere of “Don’t Worry Darling.” “Malala loved that,” Kimmel says.

Jimmy Kimmel rides in the back of a jeep as Weird Barbie (Kate McKinnon) drives around the Oscar stage, both wearing goggles.
In a promo for the upcoming Oscars, Jimmy Kimmel goes for a ride with Weird Barbie (Kate McKinnon.
(Eric McCandless / Disney)

As for viewers’ assumption that she was bothered by the bit, he responds, “There’s nothing you could do about that, unfortunately, but it happens. It’s just something that you have to accept. Last year, I said something about Irish people drinking — my dad is Irish, this is not something I imagined would come off as racist, but to certain people, it did. I tried that joke out 40 different times with 40 different people, and no one ever raised that red flag.” Kimmel pauses, impishly adding, “I should say green flag.”

Kimmel is in Vegas for Super Bowl LVIII, and the event always makes him reminisce. Yes, he’s a football fan, but the sport has been pivotal in the history of his talk show. “Jimmy Kimmel Live” launched in January 2003, airing right after Super Bowl XXXVII. But even before then, Kimmel’s connection to football in the public’s mind was cemented by the four seasons he spent on “Fox NFL Sunday,” where he made predictions. That’s when his idol and eventual friend David Letterman became aware of Kimmel, booking him on “Late Show.” “I did his show a bunch of times, and that’s what attracted the attention of the ABC executives.”


“Jimmy Kimmel Live!” quickly established itself as an alternative to the other late-night programs. Conan O’Brien’s humor was brainy, the product of a Harvard-educated prankster. Letterman was the revered elder statesman. Meanwhile, Kimmel was the everyman you’d invite over to watch the game and have a beer. A fan of Don Rickles and Howard Stern, he didn’t approach comedy with a scientist’s mind but, rather, like a backslapping buddy. That he’s now the current longest-running network host is as funny as any joke Kimmel has ever delivered — we all woke up one day and Kimmel became the gray eminence, the old guard, that guy who hosts the Oscars.

Jimmy Kimmel poses for a photo wearing a tux and sitting on a stool.
“I did not think I would ever do it again,” Jimmy Kimmel says of hosting the Oscars for a fourth time on March 10.
(Mark Seliger / Disney)

“I still feel like the altar boy who is goofing on the priest,” he insists. “I think that most people always think of themselves the way they have always thought of themselves. I’m as surprised as anyone could be in this position — even to have a really good job is a surprise to me.”

Yet he’s considering walking away. On an episode of “Strike Force Five,” the podcast he recorded with his fellow talk-show hosts during the writers’ strike, he confessed he’d pondered ending “Jimmy Kimmel Live” — it was the strike that made him realize how much he still enjoyed it.

“It’s hard to yearn for it when you’re doing it,” he says, laughing. “Wednesday night, I was very tired and I had all these scripts to go through — I had to revise and rewrite all these pitch ideas for the Oscars — and I was literally nodding off onto my computer. In those moments, I think, ‘I cannot wait until my contract is over.’ But then, I take the summer off or I go on strike, and you start going, ‘Yeah, I miss the fun stuff.’ ”


Still, he says, “I think this is my final contract. I hate to even say it, because everyone’s laughing at me now — each time I think that, and then it turns out to be not the case. I still have a little more than two years left on my contract, and that seems pretty good. That seems like enough.”

What might Future Jimmy look like? “He is very accomplished,” replies Kimmel, riffing. “He speaks Italian, he plays the harmonica beautifully. He is an expert fly-fisherman. He does all these different things that I know I’m not actually going to do. He’s drawn some graphic novels that were very well-received. He’s very busy — it’s funny, whenever I think of what I’m going to do when I stop working, it all involves more work.”

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Kimmel’s laughing, but he’s very serious about figuring out what his life will look like after the talk show. “I don’t know exactly what I will do,” he says. “It might not be anything that anyone other than me is aware of. I have a lot of hobbies — I love to cook, I love to draw, I imagine myself learning to do sculptures. I know that when I die, if I’m fortunate enough to die on my own terms in my own bed, I’m going to think, ‘Oh, I was never able to get to this, and I was never able to get to that.’ I just know it about myself.”

That realization makes him melancholy. And it makes him think of a painful memory. “I know that’s how my grandfather felt when he died — there were just so many things he had left to do.” He pauses, a little emotion in his voice when he speaks again. “It bums me out a little bit.”

Anyone who has followed Kimmel’s career will not be surprised by that gentler, more vulnerable side. The first year he hosted the Oscars, 2017, was a watershed period for him. After calmly navigating that show’s wild mix-up of a finale, he continued finding himself having to grapple with uncertainty in real time. “Jimmy Kimmel Live” gave him an opportunity to decry Donald Trump’s presidency, but even that didn’t compare to Kimmel’s raw monologue in May of that year when he talked about his son Billy, who needed open-heart surgery shortly after his birth. Widely praised for his more reflective and opinionated turn, Kimmel seemed to be entering a new stage in front of our eyes — still funny but also warmer and unguarded.


Former President Barack Obama chats with Jimmy Kimmel in 2015 on "Jimmy Kimmel Live."
Jimmy Kimmel has used his talk show to welcome Barack Obama, and to decry Donald Trump.
(Randy Holmes/Randy Holmes/ABC)

“When I think about that year, I don’t think about my career at all,” he says. “I think about our son and that experience and what we went through and just how you wind up reevaluating your life and what’s important and what isn’t — and also being reminded of how lucky you are and how lucky some people aren’t. My son has to have another open-heart surgery, so it’s something that is always in the front of our minds.”

But for now, there’s a month until the Oscars, and Kimmel needs to work. He’s not sweating the people who won’t like the broadcast — he’ll just tell his jokes and make sure to keep the evening running smoothly. He never expected to be in this position — for so long, he was the sidekick on game shows or the co-host with Carolla — so why start worrying now?

“If you think about it, I did everything I could to avoid being the sole guy,” he says. “I love being involved in other people’s projects. I never had an urge to be the center of attention, and I still don’t. It’s not in my DNA. I won’t be doing stand-up after I stop doing the [talk] show — I am uncomfortable with it. I don’t like my birthday. I love being a team player.”

It’s pointed out that he’ll soon be hosting one of the most-watched programs of the year. If he wanted to avoid being the center of attention, he has a funny way of showing it.


“So much of my life makes no sense,” he replies. “I’ve stopped trying to make sense of it.”