PLAYBOY: You first got married as a kid—or, as you’ve said, as a fetus, really.
KIMMEL: I was 20 years old. I did it because that was the plan. I didn’t make the plan, but that seemed to be the plan. I was raised, I suppose, to become a traditionalist.
PLAYBOY: Plus you’ve always maintained a pretty rigid code for the women with whom you’ve allowed yourself to become involved—all three of them to be precise: your ex-wife, Gina; Sarah Silverman; and, for the past four years, Molly.
KIMMEL: Yeah, I would never date someone I’m convinced wouldn’t have dated me when I was in high school. I’m not that kind of guy. I want to be loved for who I am, not for what I do for a living.
PLAYBOY: Historically, though, you claim to have always been terrible at knowing when women had an interest in you.
KIMMEL: Yes. Or maybe I was really good at it and no women were interested in me. It was one of those two things.
PLAYBOY: Could that partly be why you married a few years after high school?
KIMMEL: Probably that was in the thought process: I’d better lock her down, better get her contractually obliged before it’s too late.
PLAYBOY: Sarah used to say she encouraged you to date other people because you had no wild oats. Also because you’d ostensibly appreciate her more by contrast.
KIMMEL: [Laughs] It wasn’t real encouragement, though. That was pretend encouragement. She knew I wasn’t going to do it.
PLAYBOY: Did you know you were going to pop the question to Molly? This was last August while you were on an African safari—and you had the ring ready.
KIMMEL: I had the ring. I enlisted her sister to help me because I have no idea. I’d bought my first engagement ring at Costco for $500, which at the time was more than two months’ salary for sure. But yes, I planned this out. We had many discussions about where we were headed, and I felt comfortable enough to propose—not that she knew when it happened. We were on one of those rich people’s safaris; it wasn’t like we were camped out in the bush. My kids were on the trip with us, and I’d talked to them first; they seemed in favor of it. So on the last night of the trip, I proposed to her in our hotel room. By then I’d been carrying this ring, jammed in my backpack, for like a week and a half, through the Olympics in London and through Africa. I was nervously checking the whole time to make sure it was still there, never trusting the hotel safes. What’s funny is the diamond probably came from Africa, then somehow made it to Beverly Hills and then back to Africa—and then back here again.
PLAYBOY: Africa seems to spiritually alter the lives of whoever visits. Had you ever been?
KIMMEL: Oh no. I turn into Woody Allen in those situations. I took a triple dose of malaria pills and got every shot I could get before we went there. I’m terrified of animals. So it really was great. We were riding around in an open jeep beside animals running wild, and you could reach out and lose your arm if you wanted to. Everybody says they have this transformational experience in Africa. It did not change my life. The closest that came to happening for me was picking up a copy of Oprah’s magazine in the airport.
PLAYBOY: Speaking of which, you shocked your faithful constituents by suddenly becoming an impassioned disciple of Oprah after she appeared on your Oscar night special last year. Were you in fact transformed?
KIMMEL: I shocked myself. I’ve done more jokes about Oprah than about any other celebrity, so the idea that she’s now a sun that I worship is crazy. Completely unbeknownst to her, I started off on a bad foot with Oprah. My ex-wife loved her and would regularly use against me whatever Oprah had said on her show that day. I almost got to the point of delusional paranoia, like, Why is Oprah fucking with me? I was secretly worried the whole day we taped our comedy bits together that at some point she was going to pull me into a corner, put a knife to my throat and say, “Listen, motherfucker, I know the shit you said about me. I’ll cut you from ear to ear!” But I learned that even Oprah is bigger than Oprah and that I was merely a pecking little bird on the back of a magnificent steed. At the end of the day she gave a speech to my staff, telling them how great they were, and then had cases of champagne brought in. She just makes people feel good—and that’s the secret, if there is one. It was then that I fully understood the power of Oprah. Also, I had a rash and she touched me and it instantly went away.
PLAYBOY: Have you and Sarah come out on the other side of your breakup—after almost seven years together—in a friendly zone?
KIMMEL: Definitely. I’ve said we’re now like brothers. There just needed to be a period of complete separation and silence for a while. Then you kind of move on with your lives and things are going well for both of you and it’s not as painful to communicate anymore. We have a real history, and some people think the way to go is to pretend it never happened or to erase it or run from it. But Sarah and I were good friends and still are. It doesn’t go away just because we broke up. We didn’t break up in an ugly way. It was definitely no fun, but it was relatively civilized.
PLAYBOY: How do you two connect these days? In her otherwise candid 2010 memoir, The Bedwetter, you’re barely mentioned.
KIMMEL: She wrote that book right when the wounds were still fresh. It would’ve been uncomfortable—for both of us—if she’d written about the relationship. Plus she knows I’m uncomfortable sharing the details of my personal life, even with the person with whom I’m involved. Nowadays we mostly e-mail. We don’t talk that much, but we’ve intersected at some events. I took a good picture of Sarah and Molly together at a party last year, in fact. They like each other. The picture, of course, was for Cousin Sal.
PLAYBOY: You talk twice a week to a therapist—via iChat from your home—which boldly defies the old-school bugaboo about comedians avoiding psychiatry because they fear it will make them less funny.
KIMMEL: Woody Allen disproved that theory a long time ago. Some comics romanticize misery. Some of them seem to believe that happy equals shallow and anguish is an indicator of depth. It isn’t. They’re unrelated. What is more important to comedy than self-examination?
PLAYBOY: So tell us what self-examination has taught you about yourself.
KIMMEL: I’ve learned that anxiety affects almost every decision I make. I’ve learned about boundaries, though I still have trouble enforcing them. I have a hard time saying no to people. I’ve learned that most arguments have little to do with what you’re arguing about—that what people want most is to know they’re being heard. Through most of my life my goal was to “win” an argument. I was missing the point. That realization has been a great help to me. And I will fight to the death any man who dares say it hasn’t.
PLAYBOY: You’re now pitted against the big boys at 11:35 p.m. in that never-ending fight known as the Late-Night War. What would winning there feel like?
KIMMEL: I am stupidly competitive, especially when it comes to baseball or Scrabble. I play even the most casual game of softball like Pete Rose would play game seven of the World Series. I slide headfirst, I run out every ground ball, and yet I don’t feel late night is such a big competition. I mean we’re now at the point where a lot more people watch our show online than on television. People can cherry-pick the best stuff you do, which is why you don’t get 10 million people watching like Johnny Carson did. I remember when I was a kid, if Letterman had a guest I wanted to see, there was only one way to see it—stay up and watch. You don’t have that anymore. The genie’s out of the bottle. There won’t be another king of late night to match Carson’s dominance. There will be maybe a bunch of dukes and the occasional earl. I should add here that Dave transcends any time slot; he is the father of comedy as we now know it. I wonder if he knows what he means to every comedian under 50 years old. That NBC Late Night With David Letterman show was a revelation.
PLAYBOY: You were 14 when that show debuted. You have admitted you were obsessed: Late Night–themed birthday parties, the l8 nite license plate on your first car.
KIMMEL: Some kids drew the Van Halen logo on their notebooks; I drew Dave’s face on mine. I was authentically inspired by him, maybe to the deepest fanatical extreme. But it was sincere idolizing. I understood even then that he was changing everything with that mix of quiet sarcasm and by just standing further back from the absurdities of life than anyone on television ever had, in order to show us things as they really are.
PLAYBOY: Few people know that during the very first broadcast of JKL, you secretly wore the official T-shirt from Dave’s old Late Night show.
KIMMEL: That’s true. Our then head writer, Steve O’Donnell, who had also been Dave’s original Late Night head writer, gifted me with it the day of our first broadcast, and I decided to wear it under my shirt. It was meaningful.
PLAYBOY: What does Jay Leno mean to you?
KIMMEL: I had loved him from his early appearances on the Letterman show. Some friends once bumped into him at the airport and, for my 21st birthday, had him sign a pizza box for me. He drew his little face on it. Strangely I don’t even like talking about him anymore. The only time I think about him is when I’m asked. I believe he’s not just a smart politician but also a smart guy. I haven’t met anyone who knows more than he does about how ratings and the business of late-night television work. Last fall, when Dave finally came on my show—which was clearly the greatest thrill of my career—somebody suggested, “Well, maybe you guys should talk about Leno.” But for me that night was about my fondness for David Letterman, and Jay Leno had nothing to do with it. I didn’t want him soiling our time together. When I’ve gone on Dave’s show, I think it’s been more relevant to make fun of Leno.
PLAYBOY: You excelled at it, especially back in 2010 when he abruptly repossessed The Tonight Show from Conan O’Brien after his nightly prime-time Jay Leno Show had failed. You even imitated him, with the help of prosthetics, for a full installment of your own show. No mercy there at all?
KIMMEL: I don’t know. I always feel bad if I hurt anybody’s feelings, but I don’t believe Jay Leno has actual feelings, and he doesn’t seem to be that worried about other people’s feelings. Anyway, I can do a pretty good Leno imitation. It was a lot of fun to be him—also much easier, particularly in constructing “his” monologue for that night. I have a filter mechanism in my head every night when I put together the monologue for our show: If I can imagine Jay Leno telling a joke, then I won’t do it, even if it’s a good joke. There are three ways he does a joke, every single time, always with the same rhythm. The difference between Leno’s jokes and Letterman’s jokes is like the difference between Celebrity Jeopardy! and regular Jeopardy! During Celebrity Jeopardy! anyone could get all the answers; there’s an accessibility that makes you feel like you’re smart. I think Leno’s jokes are similar in that way. Real Jeopardy! requires an attempt at greater mind function.
PLAYBOY: Admirably, you never broke character as Leno—though toward the end of that show you said, “Man, I’m getting tired of this.” Your memorable moment came later that week when Leno had you appear via satellite on his prime-time show’s 10 @ 10 quiz game.
KIMMEL: That was thrilling—it really was—and also kind of dangerous, because I realized he wanted to communicate to America that it was all just a friendly joke. That was the perception Leno clearly wanted out there. The more I thought about it the madder it made me. I didn’t want him to just get away scot-free with what was happening all over again. Keep in mind this was the second time he’d done this. The first time, he’d elbowed Dave out of the Tonight Show gig, and now he’d done it to Conan. I felt there had to be some kind of comeuppance—not that I knew I’d do what I did. I assumed their plan was for us to at least playfully have it out on-air. Of course, other than a brief mention of my imitation, not even one of the 10 questions he asked was related to the controversy—as if none of it had ever happened. So I decided to jokingly bring every answer back to the Conan situation. I have to say I was surprised by Jay, because he just clung to that card full of innocuous questions no matter how I jabbed him. The smartest thing he could have done after the first two questions would be to say, “All right, that was 2 @ 10 with Jimmy Kimmel—we’ll be right back!” That he didn’t return fire, I still don’t understand at all. It was almost as though he leaned into the punches.
PLAYBOY: Did you ever speak with Conan during that period?
KIMMEL: No, but we’ve met at a couple of parties since. He was very, very funny and nice. We really didn’t talk about it, though. I don’t know that he took any pleasure out of that time in his life. I doubt he ever happily reminisces about it.
PLAYBOY: Letterman appeared on your show last fall, during a week of JKL broadcasts from Brooklyn. Naturally, he squirmed throughout your professions of love, but he also said, “I think you’re gonna be perfect at 11:35 p.m. I couldn’t be happier to have you in the running.”
KIMMEL: Some people interpreted that as a passing of the torch, whereas I’m pretty sure it was more like the passing of a Bic lighter—very generously, nonetheless. I know Dave is more uncomfortable with praise than any person who’s ever lived. I decided it would mean more to viewers if I showed those teenage pictures of my Late Night birthday cake and license plate to prove that I wasn’t just kissing his ass and that these are not things I made up. Ultimately I chose to make him a little bit uncomfortable and hope that he could deal with that. By now he definitely knows it’s authentic, and he must appreciate it or else why would he do the show? Not because he’s a fan of mine. Let’s be honest—he’s doing it to be nice. But I sensed, toward the end, he started to warm up to my compliments. After we finished he said to me, “Let’s start over and do it again.”
PLAYBOY: The fact that you were selected to pay tribute to him onstage at last December’s Kennedy Center Honors ceremony suggests he holds you in no small regard. Plus he had to enjoy your reference to that medal hanging around his neck: “There’s a 40 percent chance he’ll hang himself with it.”
KIMMEL: He was very gracious at the dinner after the show. He thanked me and asked me to “please stop doing this.” But the highlight of the night came earlier, on the red carpet, where reporters from various entertainment news programs ask you why you’re there and what Dave means to you. As Dave passed behind me, he gave me a hard, one-handed shove into a row of budding Mario Lopezes. Or is it Mario Lopezi? I’m not sure. What I do know is that Dave shoved me.