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Wesley Mann / AUGUST

You might say that the late night television personality and upcoming Oscars host has complicated relationships. He’s married to his (now) lead writer, he’s had his ex as a guest on his show—multiple times—and he can’t stop pranking his friends. This is a man who believes that discomfort is a small price to pay for affection.

When You Work with Your Wife, She’s Your Work Wife, Not Your Wife Wife
When the office is essentially your kingdom, there are no no-no’s. I mean, these two guys sitting here in my office, if I told them “I’m about to have my way with you—” [addresses his office, off the phone: What would you guys say?] “Yes, dear,” is what they said. Well, one said, “Cool.” The other one is running. But I don’t think my wife would classify it as an [office] romance. More an abduction. It’s hard to make the flip from boss to equal partner. And it’s especially hard for my wife [Jimmy Kimmel Live! co-head writer Molly McNearney], who’s under the impression that she’s the boss and I’m the equal partner. She says, “K.I.P.” Keep it professional. Because I embarrass her here at work. When we have our writers’ meetings, I’ll sit real close, as if we’re at a party. She really doesn’t like it. She doesn’t want to be touched by me here at the office. No one does. No one will let me touch them here.

Never Prank Anyone Richer Than You…
I was at George Clooney’s house, and he said, “No one has ever swum back and forth in this pool four times without coming up for air.” And I looked at the pool, and I thought, “Huh, I think I could be the first guy to do this. I have pretty good lung capacity.” Everyone cheered me on. And I go underwater, and I swim the first lap and the second lap. And the third lap, I’m really running out of air. And the fourth lap, I’m like, “Oh, my God. I might die in here.” But I was determined to impress George Clooney. And when I made it to lap four, I came up triumphantly…and no one was there. He had escorted everyone back into the house. I know better than to get him back. He’s got a devious mind and an unlimited amount of money.

…But Prank Your Family
Once, [my] Aunt Chippy was talking about her next-door neighbor, Lillian, who she does not like at all—and by the way, my telling you this is going to cause a problem. So when she was on the show, I say, “Hey, what about Lillian, your neighbor? You told me you don’t like her.” And then the next day I have a friend go and pin a note on her front door that says, “I heard you on your nephew’s show last night. Come over and let’s discuss this.” So she hides in her house for the whole weekend, looking out of the window, with the curtains drawn, to make sure this woman’s car is not in the driveway. She finally went over to her house and said, “Lillian, I got your note.” And Lillian said, “What note?” And there was a moment of realization. And she went back home and called me and was screaming and cursing at me.

If You Don’t Know How to Have Adult Relationships, Date Someone Who Does
Sarah [Silverman] and I, we’re like brothers. It doesn’t make sense to me that people would erase a big part of their lives. It’s not like we didn’t spend every day together for many years. We did, and we have a lot of things in common and mutual friends. I’ll see something in the news and think, Oh, my God. I have to tell Sarah about this. She has a very good relationship with pretty much all of the guys she’s dated. She is very mature about it. And I’m nothing if not mature, as you’ve probably gathered from this interview.

Everyone Likes Being Told They’re Funny—Even Me
Every year, my wife makes a book of stupid things I’ve said to her in bed—“I’m gonna dump the contents of your purse all over your stomach,” “Everyone is now calling the butthole the battlehole. I changed the game,” stuff like that—because she knows there’s nothing I find more entertaining than things I’ve said. I think that holds true for anyone. That’s a great note for people who are going to speak at a funeral or a wedding or a major event of some kind: The best way to honor someone is to tell a funny story in which the person you’re telling the story about was funny.

It’s Harder to Screw Up Kids Than You Think
My mother used to prank us by lying on the ground and pretending to be dead until we cried. That’s the number one piece of parenting advice that I would say not to follow. But my mother also used to do these weird characters every night. One of them was like a hunchback character. Another one was a street fighter. She would take me on these emotional roller coasters. I think parents worry too much. Ultimately, we can allow our kids to consume anything—thoughts or things that we see or a half pound of pasta every day—and they’ll be no different from any other kid by the time they hit 12. Parenting is like sports: If you’re too careful, you’re going to lose. But, to reiterate, do not play dead.

A version of this story originally appeared in the March 2017 issue with the title “A Modest Proposal.”

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