PLAYBOY: Then again, are you technically a broadcaster first and a comedian second? That was David Letterman’s path.
KIMMEL: Dave did radio, local television and then a lot of stand-up comedy when he moved to L.A. I hadn’t done anything like that. I was a radio guy and thought I would always be a radio guy. That was my only goal. People mistakenly think I’d been planning to host a late-night talk show since I was a kid. I wish that was the case because it’s a better story—and I did deeply worship Letterman, no question. But I’m not a stand-up, and furthermore, it never dawned on me as a kid that there could be other talk shows besides Dave’s and Johnny’s. I looked with disdain on anybody who tried to start a new one. It was off-putting to me that Pat Sajak or Rick Dees would dare go up against Johnny Carson. I resented them for trying. Frankly, those shows never worked anyway.
PLAYBOY: Is it true you’re never nervous before show time?
KIMMEL: Yeah, very rarely. It’s just the rhythm you have to get into. You have no choice but to do it, so you just do it. In fact, I can’t remember the last time I was nervous. Do you think any of the hosts are? I mean, at a certain point, how could you be? Your metabolism will acclimate. Maybe it’s like being a homicide detective. You’re horrified by the first 50 dead bodies you see splayed all over the sidewalk, but eventually you’re propping one up to take your Christmas-card photograph with a decapitated head.
PLAYBOY: ABC brought you aboard to draw male viewers, basically your Man Show fan base. Ironically, soon after that the network’s prime-time demographics became hugely female. Were adjustments made to become more women-friendly?
KIMMEL: On some level, yes. For me it was not a matter of the things I did; it was the things I chose not to do that made an impact. Our show had a lot of staff from The Man Show, and the sensibility hadn’t changed much. But there came a certain point when I knew change had arrived. It was when Steve-O, the Jackass stunt maniac, came on and wanted me to do a bit in which I’d throw darts into his ass. And I said, “You know what? Not only do I not want to do that, I wouldn’t even want to see that.” I don’t know anyone who would want to see that. I’m sure certain people out there might, but I didn’t think it was right for our show.
PLAYBOY: Was that your turning point?
KIMMEL: It really was. That’s the moment I grew up: when I declined Steve-O’s invitation to throw darts into his ass.
PLAYBOY: You demonstrated another big stride in TV maturity when you finally consented to wearing ties. You’d held out on that one for almost three years.
KIMMEL: I finally put on a tie, yeah. Before that I’d sometimes wear one as part of a costume, and whenever I did everybody at ABC would be thrilled: “Oh! You look so great in that tie!” Even Disney-ABC chairman Michael Eisner would try to convince me to wear the tie. The reason I didn’t is because I felt it was a “give” that I could rely on later—like a chit. I held back until they became insistent, and then I gave in, which kept them happy for at least a year. The tie made them feel like I was listening to them. And of course it was the right decision. We have this idea that television executives don’t know anything and we know everything. The truth is they know just as much stuff as we do, and as much as you don’t want to say it, sometimes they’re right.
PLAYBOY: Only Craig Ferguson has dared to keep his tie loosened.
KIMMEL: Yeah, it’s to reflect how casual and off-the-cuff he is. His tie is askew. You don’t plan that—it just happens.
PLAYBOY: You’ve thrown some notorious star-studded parties in your home, welcoming everyone from Howard Stern to Don Rickles. What’s your secret to great party giving?
KIMMEL: I don’t know. I’m not a great partygoer. When I go to a party all I want to do is go home. I like having parties because I don’t have to go home. I already am home.
PLAYBOY: But doesn’t the host have the least fun?
KIMMEL: Theoretically yes, the party host has the least fun. But it’s worth it to not feel uncomfortable in other people’s houses. I do know you need to have cocktails and something to eat. If you put a little extra effort into these things, it surprises and impresses people.
PLAYBOY: What did it take to successfully entertain Rickles?
KIMMEL: I guess a mixture of pride—which I always take in preparing a meal for people—and also fear, knowing the insults would never end if anything was even slightly out of place. I know it went well, though, because all Don criticized was the stairs he had to walk up. To hear him explain it, it was like scaling the side of Rapunzel’s castle. But the reality is there are six steps leading up to my front door, and he came in the back way. He just didn’t like the idea of stairs in general.
PLAYBOY: Historically, what’s the one surefire dish you serve that people love?
KIMMEL: Pizza. Chris Bianco, the world-famous pizza chef from Phoenix, taught me as much as I can learn without the benefit of his 30 years of experience. I can get to about 84 percent in terms of replicating his pizzas, which is pretty great. I’ve got a brick pizza oven in the backyard. No one has ever been disappointed. And you can tell when people really like something; they go through an emotional process, like “Oh my God! Wow, this is good!” But please let me point out that 95 percent of the events at my home do not involve celebrities of any kind.
PLAYBOY: That wasn’t the case with your weekly multiscreen Football Sunday game-viewing parties—which stopped a couple of years ago. Guests on your show would openly beg for invites.
KIMMEL: That was mostly the result of Adam Carolla and Bill Simmons of ESPN talking about it on their podcasts and radio shows and websites. Celebrity-wise, there’d be occasional drop-ins like Tom Arnold, Kathy Griffin, Jon Hamm pre–Mad Men—but mainly it was a lot of Man Show staff guys and friends who, after my marriage ended, I began having over to watch football every Sunday. It finally got overwhelming. I’d spend almost all of Saturday shopping and cooking, and then Sunday preparing everything while watching the games with them. Then they started asking if they could bring other friends, and I’d say okay, and those friends of friends would come every week and become part of the group, and then eventually the friends of friends brought along more friends, who also became regulars. It just got so big that I was too busy to barely even glance up at any of the games.
PLAYBOY: Proving once again that party hosts do have the least fun.
KIMMEL: More like proving the sad fact that I never have the heart to tell anyone no.
PLAYBOY: But then Tom Cruise asked you about it on the air one night, which led to probably the strangest Football Sunday in history.
KIMMEL: True. I invited him, and Tom Cruise came over—with his mom. Now, there are a lot of fictitious versions of what happened that day, most of them perpetrated by Adam Carolla, who was so drunk at the time he remembers no actual facts. And also our pal Jeffrey Ross the comic filled a whole chapter in his book with an incorrect version.
The definitive version—to make it as concise as possible—starts, as do all idiotic stories, with Cousin Sal, who instigates evil for pleasure. In this case his victim was Jeff Ross, who months earlier had been on Dancing With the Stars and was eliminated in the first week of competition. And because we have the eliminated stars as guests immediately afterward on those same nights, you should know that we find out who got the lowest votes a little bit before the general public does. It’s a network courtesy, just to help us prepare questions. Anyway, on the afternoon of that season’s first elimination night, we had no idea yet whether Jeff had been voted off, but we did know that on the previous night he scored a 12—the lowest score of the night. So Sal, who has constantly screwed with Jeff for 10 years minimum, decided to send him a text that said, “You’re safe.” We figured Jeff would at least be suspicious. He texted back, “Really?” Sal texted, “Yes. Don’t tell anyone.”
Jeff of course instantly told his dance partner, “We’re safe!”—and then on the live broadcast later pretended to be nervous when they found themselves, naturally, as one of the two couples with the least votes. And then, surprising only him, he was eliminated. If you watch the tape you can see him mouth the words “We lost? We lost?” He looked as if he’d been hit by a train. He was so angry about this prank he wouldn’t speak to Sal for months. And they were pretty close—in fact, it’s a sore point that still lingers. Ross even avoided Football Sundays for a while but decided to show up the same day Tom Cruise decided to come—which I hadn’t told anyone. Tom arrived as promised, along with his mom, who’s a very lovely woman.
PLAYBOY: Little did they know what awaited them.
KIMMEL: Right. Tragically, Sal and Jeff had resumed sniping at each other that afternoon. After the games ended, someone—probably Sal—decided that the best way to settle this dispute would be to lay the case out for Tom and his mother. Suddenly, a courtroom scenario was set up in the living room—this was at my previous house—with Sarah acting as Jeff’s attorney and me acting as Sal’s. Sarah and I were still together then. We carefully presented all the insane details of the case to Tom and his mom, who graciously agreed—after already being at my house for seven hours—to spend another two hours listening to this nonsense, with Tom earnestly questioning both defendants. In the end, Tom deferred to his mother because he ultimately didn’t know what to make of such lunacy. And his mother said, “I think you’re both acting like little boys.” Which pretty much shut it down, appropriately. So no resolution ever came, but it was fun to purge and play it out, which kind of healed that ridiculous situation.
PLAYBOY: Then there was the Carolla version to straighten out.
KIMMEL: Yes. Carolla told a separate story about that day in his book, which I pointed out to him was untrue and which he then realized was untrue. He’d forgotten how smashed he’d been. But Adam long ago invented a victory dance where he makes it look like he’s shitting a football out of his ass while reading a newspaper. It’s very funny. He demonstrated it to Tom and Tom’s mom—not that they asked for it; he just did it. And they also thought it was very funny. Then Adam went home. In Adam’s book, however, they were so offended that they left in a huff. But the truth is they stayed another five hours after Adam left. I was especially annoyed when I read his story because it makes Tom Cruise look like a humorless dick when that wasn’t the case at all.
PLAYBOY: You once lamented, “I wish I could enjoy things more in the moment.” How are you doing with that?
KIMMEL: Not doing well with that, frankly. That situation really hasn’t changed. [laughs]
PLAYBOY: Yet on your show you clearly thrive in the moment, dependably asking fun questions none of your competitors think to ask and also actually listening to guests—which is a great lost art among late-night hosts.
KIMMEL: Hmm? I’m sorry. I wasn’t paying attention.
PLAYBOY: Exactly. But you do adhere to the Howard Stern school of probing guests for answers the public truly wants to hear.
KIMMEL: Nobody does it like Howard. By now, if somebody wants to be on his show, they’re prepared to face the consequences, whereas we have a merry-go-round of publicists and celebrities to please. Increasingly, guests also know what they’re getting into with us and aren’t surprised if I ask a weird question. I just try to put myself in their real-life shoes when figuring what I might ask. We recently had Daniel Craig on, and mainly I was thinking about the fact that he’s James Bond and how great it must be to be James Bond and how pleased with myself I would be if I were James Bond. I’d probably look at myself in the mirror constantly and repeat over and over again “Bond. James Bond.” That would be very enjoyable.
PLAYBOY: If not in the moment, can you enjoy things in retrospect?
KIMMEL: Overall I enjoy life, but I also have too much work to do. Whenever I’m relaxing I feel like I’m being lazy—that there’s something I need to attend to. I’m almost always preoccupied, like I’m nearly drowning at all times when it comes to work and returning e-mails and revising scripts and on and on. The only way to alleviate that anxiety for me is to get stuff done. Theoretically if I didn’t have as much work to do I could relax. Who knows what the reality would be without the work? What I do know is when I go on vacation I’m quite able to enjoy myself. If I go away and don’t have any deadlines looming, then no problem.
PLAYBOY: So outside of the context of everyday life, you’re able to relax. Does that mean even if you’re at home, there’s no sanctuary for you?
KIMMEL: Right. Because if I’m here at home—well, see those pictures stacked over there? [points across the room] They still haven’t been hung because I haven’t figured out where I want to put them, and this drives me crazy. There are so many things I feel need to be done that it’s impossible not to worry about what I should do next.
PLAYBOY: Your last home was more of a bachelor dream playhouse, whereas you now have an aesthetically elegant sprawl here. Is that on purpose?
KIMMEL: Yeah, I wanted to have a more grown-up house. I’ve been here three years, and it’s still in transition. Since Molly moved in, though, it’s gotten more homey. There are flowers in the house now, which is not the sort of thing that would’ve occurred to me. It’s a nice look.
PLAYBOY: Molly McNearney is your co–head writer, and you two have a summer wedding planned. Do you consider yourself a romantic?
KIMMEL: Not particularly. I’m more a traditionalist than a romantic. I am not the most communicative person, so any real expression of my emotion is greatly appreciated. I write notes. It’s easier for me to express love in writing. When I try to do it one-on-one it usually turns into a joke. I have a tendency to ruin things.