As Jimmy Kimmel sees it, hosting the Oscars is a lot like taking a plane trip.

“You don’t think too much about it if it went well,” he explains. “If it was terrible, you tell everyone you know about it — the turbulence, the delay, how long you had to sit in the airport waiting.” Kimmel, who will be emceeing for his fourth time, concludes, “We just want a flight that’s on time and cocktails are served and nobody throws up.”

Between prepping for the March 10 telecast and his ABC late night series, which share a team of writers, he and his executive producer and wife, Molly McNearney, hopped on a Zoom to discuss his ideal audience, famous frenemy Matt Damon and his wish for Golden Globes host Jo Koy.

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What is the process that lands you at, “Yes, I’ll do it again”?

KIMMEL It’s different for both of us. I think Molly waits till I come up with the yes and then tries to talk me out of it. And if it’s still yes, then it becomes “yes!”

MCNEARNEY That’s exactly right. I remind him of all the obstacles, and if he still wants to do it, then I feel like he’s committed to it.

KIMMEL Really, it’s exactly how we got married. The same dynamic.

MCNEARNEY Absolutely true. (Laughs) I think the strike played a part, too. It was giving people job opportunities and also having a roomful of people who appreciate their jobs more than ever and making movies again felt like a good wave to ride. Do you agree with that?

KIMMEL Yeah. I mean, I’m just now thinking of it, but yeah.

MCNEARNEY Oh, I thought about it.

KIMMEL No, no, I did. I definitely thought our writers would appreciate a check. (Laughs)

On nominations morning, as joke writers, what were you two hoping to see?

KIMMEL Well, you want the big stars to be there. If your choice is between having Leonardo DiCaprio in the audience versus not, you want to have him there.

MCNEARNEY And it was a big relief to us as joke writers to have movies nominated that the home audience has seen, like Barbie and Oppenheimer.

I assume the fact that Matt Damon is in one of them is also a plus?

KIMMEL I was unaware he was in one. Which one is he in?

MCNEARNEY We don’t talk about that. He’s my screen saver, but no.

How much do you think about playing to those in the theater versus the audience at home?

KIMMEL I was distracted. I just thought of Matt Damon is DunKen, like the donut.

MCNEARNEY Oh God, he wrote it down.

KIMMEL Sorry, I’m going to let Molly answer that. I wasn’t …

MCNEARNEY He wasn’t listening. I know exactly how he’d answer it, which is he always wants to make the room laugh first because if the room’s laughing with him, then the home audience is laughing. 

KIMMEL Well, that’s the advice that the great Billy Crystal gave me. You’ve got to kill in the room, and it makes sense because if nobody’s laughing, it’s not going to seem funny to the audience at home.

MCNEARNEY But there is a balance. Some great industry jokes could play really well in that room, but the home audience doesn’t know what the hell you’re talking about. 

Jo Koy caught a lot of flak hosting the Golden Globes in part because he went after folks in the room. And he isn’t a part of Hollywood in the way that you are …

KIMMEL It’s a lot easier for me than it is for Jo Koy. It’s like if a stranger walks up to you and goes, “Nice shirt, Tom Selleck.” If it’s one of your friends, you don’t take offense to it, but if it’s somebody you don’t know, you might smack him one. And not that I have any business programming the Golden Globes, but I think they should let Jo Koy host the show next year and give him a shot at doing it over. It would be very smart. I think he learned all the lessons, and he’s a funny guy. I think it would be nice for everyone. 

How much do you worry about insulting people?

KIMMEL I have such a fear of standing in front of a quiet audience but as far as people being mad, I don’t necessarily operate that way. I’m not interested in hurting anyone’s feelings, but sometimes some people are more sensitive than others and you just have to accept that. You can’t build your monologue around that. And I’m not looking to say anything mean, but not everybody’s going to love all the jokes.

Molly, do you find you’re the one who typically pushes him or urges him to dial it back?

MCNEARNEY I’m definitely safer than he is. I think it’s a good balance. I weigh on the “oh, it’s not worth it to upset someone,” but Jimmy is so good at figuring out these jokes. He really is. And he gets pages and pages and pages and pages of jokes. We’ve been writing since Christmas.

KIMMEL And then, weirdly, there are jokes that will just pop into your head as you’re reading through the teleprompter right before you go out on stage.

MCNEARNEY Or in the middle of the night or while we’re in the car with the kids, and he’ll say, “Get out your phone and write this down.” He’s constantly thinking of jokes and I’m his secretary. (Laughs)

You’re making a late-night show with the same team every night. How do you distinguish between what make sense, joke-wise, for Jimmy Kimmel Live vs the Oscars, and is that distinction always clear to you?

MCNEARNEY I think our writers appreciate a break from political jokes. Our nightly monologue is predominantly focused on the events of the day, and the Oscars are a really nice break from that.

KIMMEL If we have a really great joke or bit that’s movie related, we’ll save it for the Oscars.

Is avoiding politics at the Oscars a mandate that comes from above?

KIMMEL There are no mandates from above. I mean, nobody ever reviews the material. The last thing you’d want is someone weighing in. But the jokes themselves, if I can’t resist one, I’ll do it. If it’s an absolutely great joke, I’ll do it no matter what the topic is.

What’s the protocol for asking your famous friends to help you out on bits?

MCNEARNEY I hate it. I’ll be honest, I hate putting people in a position where they can reject us.

KIMMEL The problem is, you don’t get straight answers. You’d almost appreciate, “I just don’t think that’s funny.” Or, “I just don’t want to do that. I want to sit there and relax.” You get all sorts of crazy reasons why they’re unavailable and movie schedules that don’t actually materialize.

MCNEARNEY And I get it. They’re like, “Hey, I’m here to celebrate. I don’t need to risk any kind of backlash or cringey moment.” But we aren’t asking much of people this year. I feel like we’re really relying on what our strengths are, which is great jokes and great material, and we have a room full of amazing people.

Who are the faces in the crowd that put you most at ease?

MCNEARNEY It’s always nice to see friends in the audience, like Emily Blunt, who is a dear friend. We’re very excited for her.

KIMMEL Yeah, and there are certain people who you have a rapport with and it’s fun to see them and they’re going to be laughing, even if they don’t like it, just to be supportive. We were watching [last year’s] monologue to see what types of jokes worked and how it looked because I’d never watched it. And it’s funny when they cut to certain celebrities and they’re not paying attention or not laughing. I do write their names on a list, and I will punish them in the future.

MCNEARNEY Lady Gaga was a great audience member last year.

KIMMEL She’s on the good list.

MCNEARNEY But it’s also a terrible feeling to have a camera on you when you’re watching something. We’ve been in those situations.

KIMMEL Yeah, and you know what we do? We put a shit-eating grin on our face and throw our heads back as if it’s the funniest thing we’ve ever seen.

What is the worst-case scenario for you, Jimmy: getting called out for playing it too safe or potentially crossing a line and upsetting people?

KIMMEL I don’t feel like playing it too safe is ever a concern that I have.

MCNEARNEY No, but which would be worse for you?

KIMMEL My goal is to do neither of those things, but somebody’s always upset afterwards.

Are you a decent gauge of what will offend people at this point?

KIMMEL I think I am, but it always turns out that actually I’m not. Like, the nation of Ireland was mad at me last year. It never occurred to me. I don’t know, maybe because my dad is almost 100 percent Irish I thought I’d be in the clear on that one, but then my dad starts getting calls from his Irish relatives, like, “Why would he say that?!”

MCNEARNEY Meanwhile, your wife Molly O’Brien McNearney is on the side drinking tequila.

Having done this a few times, what would you say is the best and worst part of the night for you?

MCNEARNEY The best part? I actually really like watching people win and make their acceptance speeches. I cried a lot last year.

KIMMEL There was some great acceptance speeches last year.

MCNEARNEY Yes. An editor made us cry. When does that happen?

KIMMEL For me, the best part is, like, three hours into the show, you know how it’s gone and you can just be a little looser and a little less scripted and just poke people a bit and talk about things that are going on in the show.

MCNEARNEY That’s really fun to observe as a writer and a producer. He really does just become observational at that point. He has his script but then he is looking for what’s going on in the room and how we can play with it and respond to it.

KIMMEL And the worst part? After the show when I’m just tired.

MCNEARNEY He doesn’t want to go anywhere.

KIMMEL I’ve been standing for too long!

MCNEARNEY It’s annoying. This is what happens every time we get in the car: I’m excited to go to these parties and have a drink and celebrate these months of work, and all he wants to do is go to sleep. It’s like watching someone unplug.

KIMMEL It’s like the Macy’s Thanksgiving Day parade, and I’m one of the floats.

What typically happens? As in, who wins?

MCNEARNEY I win for about 45 minutes at the Vanity Fair party, and then I’m ready to go to the Beyonce party and he’s like, “Nope, time for bed.” And I can’t get into parties without him. You know how this town works!

So, do you think you’ll go for a fifth time?

KIMMEL I would be very foolish to make that decision now, or really anytime before next September. But we think we have a pretty funny show. We’re excited about it.

Shifting gears, you’ve seemed surprised by the perpetual interest in your retirement plans, but you’ve also publicly flirted with retiring for so long. I mean, Seth Meyers called you the Tom Brady of late night.

KIMMEL I think of myself more like the Cher of late night. (Laughs) I will say this, I’ve got to stop answering this question because whatever mood I’m in is the way I go, and then it upsets everyone that I work with.

Molly, do you waffle as much as he does?

MCNEARNEY I go back and forth between approaching it from a personal point of view and a professional one. From a personal point of view, I look at his lifestyle and say, “How much longer can you do this?” I mean, it’s a grind. I don’t think anyone has any idea how much this man works. He’s going from seven in the morning to well after 11, maybe midnight, most nights. It’s a real commitment and also it can start to take a psychological toll being responsible for digesting the news every day and then helping America understand it. So, from a personal point of view, I say, “That’s enough, let’s hang it up and maybe spend some more time with our kids.”

And from a professional one?

MCNEARNEY From a professional point of view, I say, “Why wouldn’t he keep going if he could?” He’s really, really good at it. And I think we need his voice. He holds people accountable and he’s very funny. So, it’s really tricky for me, but ultimately he’ll make the right decision for him and for the show and I’ll be fully supportive of whatever he wants to do. I didn’t know he’d pick up this last contract. I mean, I did know, obviously I was part of the conversation, I didn’t learn from an article that you wrote, but he was definitely ready to be done this last time and then he changed his mind at the very last minute.

KIMMEL I got worked over is what happened.

Now you’re heading into another election year where it’s likely to be all Trump all the time for you. Are you prepared for that?

KIMMEL You know what, I kind of love it because I know it bothers him and that really tickles me. And then occasionally we get confirmation of that and it inspires me. He is my muse.

MCNEARNEY There have been moments where Jimmy has wanted to do a show on a Saturday or Sunday because there has been something crazy.

KIMMEL Oh, when that verdict came in on Friday, I’m like, “Do we have to have a three-day weekend?”

MCNEARNEY Oh, he wanted to put shows up all weekend.

And that’s why he keeps signing on for more…  

KIMMEL Yep. I did it for Donald.

An abbreviated version of this story first appeared in the Feb. 28 issue of The Hollywood Reporter magazine. Click here to subscribe.

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