When Jimmy Kimmel Live debuted on January 26, 2003—on the heels of Super Bowl XXXVII and prefaced by a joking warning to viewers from anchor eminence Ted Koppel to expect “no special post–Super Bowl edition of Nightline tonight so that ABC can bring you the following piece of garbage”—not many people thought the show would survive a year. “Welcome to Enjoy It While It Lasts, my new talk show,” said Jimmy Kimmel that first broadcast. The young midnight upstart, who followed Nightline on ABC until Nightline was relegated to following him earlier this year, is now fully engaged in a head-on battle at 11:35 p.m. with his late-night elders, NBC’s Jay Leno and CBS’s David Letterman. JKL’s dependably okay ratings—which, in fact, have spiked in recent years—have less to do with the seismic move than with the show’s lure of advertiser-treasured 18- to 49-year-olds, exceeding even that of the other, younger Jimmy (Fallon) on NBC.

At 45 and 20 pounds slimmer than in 2003, the Brooklyn-born, Las Vegas–raised Kimmel has slowly reshaped his longtime lowbrow image—a residual effect of four years of co-presiding over Comedy Central’s The Man Show (itself a culmination of his earlier radio shock-jockeying)—into a talent worthy of playing in the majors. His rise has been slow but steady, based on his willingness to take chances and exploit social media. The JKL online viral music-video sensations “I’m Fucking Matt Damon” (perpetrated by Kimmel’s then inamorata Sarah Silverman) and the tit-for-tat “I’m Fucking Ben Affleck” begat A-list intrigue that has resulted in the show’s steady stream of elaborately produced comic videos featuring the likes of Harrison Ford, Meryl Streep, Tom Cruise, Tom Hanks, Oprah Winfrey and even first lady Michelle Obama. Last year alone he hosted both the White House Correspondents’ Dinner and the Emmys; he also became engaged to JKL co–head writer Molly McNearney (he has two grown children from his first marriage), and in the realm of dreams-come-true, he finally welcomed onto his show his lifelong idol David Letterman.

Playboy dispatched journalist Bill Zehme—an expert on the world of late-night talk shows who has spent time with and written about Letterman, Leno and Johnny Carson, and who profiled Kimmel for Playboy in 2007—to the host’s Hollywood Hills home to make him sit and think about what he’s done. Zehme reports: “Jimmy Kimmel embodies more of, well, everything than anyone I’ve known—the expansive generosity, the reflexive candor, the profound thoughtfulness, plus he cooks like a four-star chef. He gave up the bulk of his birthday weekend for our many hours of sessions, even whipping up an incomparably fine frittata during the process. Once, as we sat by his pool, he spied a few giant hawks majestically gliding above our heads and briefly recoiled before magnanimously giving them their due: ‘Look at those motherfuckers,’ he said, squirming. ‘But they’re awesome too—because they eat fuckin’ rats, so I have to love ’em.’”

PLAYBOY: Let’s begin by mentioning your nightly trademark Jimmy Kimmel Live sign-off, when you apologize to Matt Damon for bumping him due to time constraints. This interview, it turns out, had to be bumped one issue because Matt Damon was locked into doing it last issue. Can you accept our apologies?

KIMMEL: Well, isn’t that beautifully ironic? But the good news is Matt Damon won’t ever know about this because he doesn’t read playboy for the articles; he reads it purely to masturbate. So I actually feel okay with it.

PLAYBOY: Where did that sign-off come from?

KIMMEL: Out of sheer desperation—just self-deprecating sarcasm that was the result of having mostly C- and D-level guests on the show. The night I first said it was toward the end of our third year. I wish I could remember who the guests were, but they weren’t just C-level guests; they were particularly low-rent, so unremarkable that I was feeling ashamed of myself by the end of the hour. As a joke I said, “Apologies to Matt Damon; we ran out of time.” He happened to be the first A-plus-list guest that popped into my head. Our co–executive producer Jason Schrift immediately doubled over laughing, which made me much happier than I’d been. So I just kept doing it to amuse Schrifty, really. I never imagined anyone was actually still watching us at the end of the show, much less that Matt Damon would get wind of it and it would become this big thing. What’s even weirder is that the studio audience still laughs at it every single night. I don’t know if there’s ever been a joke told practically verbatim so many times on television that keeps getting laughs. It’s taken on a life of its own.

PLAYBOY: Do you remember the first reaction you got from Damon?

KIMMEL: His publicist told us he thought it was funny and that people were constantly mentioning it to him on the street. As a result, we can’t just have him on as a normal guest. It now has to be something spectacular, like his video with Sarah, “I’m Fucking Matt Damon.” He has appeared probably five or six times but always in the context of a bit that grudgingly relates to not having time for him.

PLAYBOY: How much of you is the same guy who started this show 10 years ago?

KIMMEL: One hundred percent.

PLAYBOY: Really? You do know that the perception of who you are has changed considerably.

KIMMEL: Well, I think the perception of me is more accurate now. Back then, people believed I was some kind of cross between Andrew Dice Clay and one of those windup penises that hop across desktops. That was never me. That was the conceit of The Man Show—which was designed as a satire of irresponsible male stupidity and instead became a magnet for a huge segment of dopey guys who didn’t understand we were making fun of them. But when we started that show, I was a crazed, overly responsible guy who had already been married for 11 years, with two children. People are still shocked to learn I have kids.

PLAYBOY: Who are, in fact, the oldest offspring among all the late-night hosts.

KIMMEL: Yes, my kids are now in their 40s. Actually, both my son and daughter are in college, but when they were little kids they, along with my ex-wife, would occasionally appear on The Man Show. People thought they were actors.

PLAYBOY: Your first Playboy Interview—just prior to the debut of Jimmy Kimmel Live—did dwell a bit along the lines of bowel movements and masturbation tips.

KIMMEL: At that point I had nothing to lose. I could say whatever I wanted. I was a sniper back then.

PLAYBOY: Let’s talk about what has changed. For instance, you estimated here 10 years ago that you’d received only 20 blow jobs in your life. Where does the tote board stand these days?

KIMMEL: Oh, the count is way higher now. It’s in the hundreds, easily. Well, maybe not easily—listen, if I were able to give myself a blow job I’m sure the number would be much, much higher. But I wasn’t blessed with that kind of flexibility.

PLAYBOY: See, right there we’ve further broadened your public perception.

KIMMEL: Along the way, though, I’ve discovered people do have a hard time believing things that are true. I’m always being asked about my lunatic family members who appear on the show: “Is that your real Cousin Sal? Is that your real Aunt Chippy and Uncle Frank?” Of course they’re my real cousin, aunt and uncle—I mean, who could invent crazy characters like them? But I guess people are used to seeing fake relationships on TV.

PLAYBOY: What about you? Are we seeing the same Jimmy we’d see offstage?

KIMMEL: I don’t have the qualities you need to be phony, which is a huge drawback in show business. I never had any option other than to be myself. I doubt I’d be able to keep it up. I’m a guy who’s not particularly handsome or well-spoken; I’m just kind of a funny guy. Starting back in my radio years, I decided to just go with that.

PLAYBOY: “Just be yourself” was Johnny Carson’s first rule for late-night hosts. And by the way, you’re much better looking than you think you are.

KIMMEL: Thank you. I see another blow job in my future.

PLAYBOY: During the first 14 months of JKL you worked with a parade of weekly co-hosts, one of whom was presidential fellatio specialist Monica Lewinsky. How were her performance skills?

KIMMEL: She was one of the worst co-hosts we had. Her one condition was that she wouldn’t talk at all about President Clinton, which left only the handbags she was selling as a conversation topic. She seemed to be fragile in general, so everyone was nervous to bring up his name around her. And by the way, after meeting her, the Clinton situation fascinates me all the more, because five minutes with that woman would tell you that this is probably not someone you’d get involved with if you wanted to keep it a secret.

PLAYBOY: Doesn’t that whole co-host period seem like a bad idea?

KIMMEL: Yes, considering that most of our co-hosts were such bizarre characters. We had some very good and very bad co-hosts. The good ones were the people with whom I was most comfortable, so they returned regularly—Adam Carolla, Sarah Silverman, Kathy Griffin, David Alan Grier, Anthony Anderson. I remember having to really sell ABC on Zach Galifianakis, which is funny now that he’s a big star, and happily, after his first night, they realized he was great. As for the bad ones, Deion Sanders was terrible. And the psychic John Edward—awful. He didn’t want to do any psychic stuff. We had Jim Belushi as our guest and of course thought it would be fun if we tried to contact John Belushi. To my amazement Jim was all for it, but John Edward didn’t want to do it. I’m convinced all psychics are completely full of shit.

PLAYBOY: Viewers also probably forget that up until August 9, 2004, you opened the show by immediately sliding behind your desk instead of taking center stage to do a monologue. Was this a renegade act of hosting hubris?

KIMMEL: No, no, it wasn’t that. I was scared to stand in front of the audience and deliver jokes. The craziest thing is, even though I had some material planned each night, I was mainly winging it for that first year and a half or so. Plus my experience onstage was limited. I was used to sitting behind a radio microphone until I started my TV work on Comedy Central’s Win Ben Stein’s Money, where I was really just a wisecracker who read the questions. Then came The Man Show, where I was onstage—for a hundred episodes—but partnered with Adam Carolla, who is a pretty great crutch if you’re looking for one. So when this show started, I think I made a good decision to just come out and follow the Regis Philbin model—sitting down and chatting with the co-hosts. It felt more comfortable. But imagine a comedian who has been onstage only a hundred times being asked to host a talk show.

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.

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.