Playboy Interview: Jimmy Kimmel

a candid conversation with tv's ultimate guy about his urethra, his new abc talk show, a marriage gone bad, masturbating in his office and why he's had only 20 blow jobs in 35 years

Hide the women and children—America's favorite knucklehead is about to turn late-night television into a beer bash full of barking fans, jerk-off jokes and bobbling bikini babes. Tonight after Nightline: Chicks on Pogo Sticks!

It could happen. Jimmy Kimmel's late-night show, Jimmy Kimmel Live, debuts this month on ABC, right after Ted Koppel and Night-line. As Kimmel's buddy Carson Daly puts it, network TV had better "look the fuck out."

Kimmel, 35, made his mark with Comedy Central's The Man Show, a middle-finger salute to all things ball-scratchingly male, including beer, football, farting and making fun of midgets. Now he has a network mandate to manhandle the midnight hour, and here's the news: He's not going to do it.

Like his hero David Letterman, Kimmel grew up with one ambition: He wanted to host a traditional talk show—only funnier. So he'll have a desk, a band and a parade of guests plugging their new films, CDs and TV shows. "There's a reason for those talk-show conventions," he says. "They work." That's why there will be no Juggy girls on the Kimmel show, no beer for the audience, no portrait of Evel Knievel and no midgets, unless Mini-Me stops by. Just a good old-fashioned chat show of the sort Jack Paar and Johnny Carson pioneered and Letterman perfected. With a manly twist, of course. Stupid penis tricks, anyone?

Kimmel was born in Brooklyn and moved with his family to Las Vegas when he was nine. As a teen he was unpopular, a TV freak who worshipped Letterman. But geeky Jimmy wasn't a total loss. He was smart and he could make people laugh. After dropping out of college he held radio jobs in Vegas, Florida and Seattle—riffing live, making prank phone calls on the air, ignoring his bosses' orders and getting fired again and again. Finally the world caught on: He scored as Jimmy the Sports Guy on KROQ radio in Los Angeles and then as co-host of the Comedy Central game show Win Ben Stein's Money. That gig won him an Emmy, and soon he moved on to a new show, teaming with his friend Adam Carolla to create Oprah's worst nightmare.

The Man Show wallowed in everything that modern, enlightened men were supposed to have left behind. Crude, lewd and unashamed, it made Kimmel a star. But The Man Show and Kimmel's hilarious appearances on Fox NFL Sunday were only a warm-up. In fact, he was getting tired of them. He was ready for something bigger and scarier—a network show that would pit him against Letterman and Jay Leno. It is a challenge that will make or break his career (consider Conan O'Brien and Chevy Chase).

We sent Kevin Cook to meet Kimmel as he planned his invasion of network TV

[Q] Playboy: Are you taking late night into the gutter?

[A] Kimmel: People expect me to do that, but I don't want to be in the gutter with Jerry Springer and Ricki Lake. Or Dr. Phil—a guy pretending to help people when he's just making spectacles out of them. That's the gutter to me. I want to be like Letterman and Leno and Conan O'Brien. So my show will look like theirs. A desk and chairs—

[Q] Playboy: What about guests?

[A] Kimmel: We'll have them. Yes, guests, and chairs for them, too. I just want to do what I watched Letterman do every night of my youth. You know how in high school, some guys play football and some are good students? I was the obsessed-with-Letterman guy.

[Q] Playboy: And it worked out.

[A] Kimmel: It doesn't get you much pussy, though. It's funny how all of this has worked out—I wasn't popular in high school, but now every drunken guy in the United States wants to be my pal. They all want to buy me a shot, and pretty soon I'm throwing up.

[Q] Playboy: You spent months picking a name for the show. Why Jimmy Kimmel Live?

[A] Kimmel: For a long time ABC held off. I think they wanted a name they could keep when they replace me. Jimmy Kimmel Live With Chris Rock—that would be awkward.

[Q] Playboy: But the chairman of ABC Entertainment is calling you "somebody we want to groom."

[A] Kimmel: He meant that literally, because my hygiene isn't the best.

[Q] Playboy: Disney president Robert Iger says, "When you look at Jimmy, there is always a feeling you can touch him." Do you want America touching you?

[A] Kimmel: As long as it steers clear of my privates.

[Q] Playboy: So that's why you'll have the desk.

[A] Kimmel: Yes. The desk will be a barrier between the hands of America and my penis.

[Q] Playboy: Do you like being on late, when people will be having sex while they watch?

[A] Kimmel: I don't, actually. I'll be like the dog in the corner of the room, except that I can't really see anything. And looking at me isn't going to help anybody have better sex. I'll probably cause more fights than couplings.

[Q] Playboy: You had some problems with the censors when you were on The Man Show. Do you expect trouble with ABC censors?

[A] Kimmel: Please call them standards and practices. They hate being called censors. But, yeah, I plan to push the rules, because they can be ridiculous. On Comedy Central you can say boner but not hard-on. I have asked to see the list of stuff I can't say, but they won't give it up. The list is in their heads. But my ABC show will be live, so it's their problem. They'll have six seconds to decide—a six-second delay to either dump out or let me go, "Hard-on! Oh, pardon me, boner."

[Q] Playboy: What else bugs you about standards and practices?

[A] Kimmel: They blur a middle finger. That is nonsense! Thumbs are fine. You can lip-synch "fuck you," and that's OK. Watch a baseball game. They might as well advertise it: "Fans, you'll see 'fuck you' in slow fuck-you motion!" But they blur a middle finger. My Comedy Central show Crank Yankers was originally called Prank Puppets, but the lawyers said the word prank would open us up to liability. My head almost exploded. They just want to cover their asses, so they say no to everything.

[Q] Playboy: Are the censors starchy right-wingers?

[A] Kimmel: Some are OK. The one we had at Comedy Central would laugh at our stuff and then kill it. For her birthday we sent her a gift basket full of dildos.

[Q] Playboy: You once said The Man Show wasn't "only for morons." What moron percentage were you shooting for?

[A] Kimmel: Hey, I know this sounds crazy, but ABC did some research, and a greater percentage of college-educated people watch The Man Show than Nightline. Smart people can be perverts, too. Benjamin Franklin wrote a whole essay about how funny farting is. Some people simply refuse to enjoy stuff like that, which is too bad for them. Caviar might be great, but McDonald's french fries are really good, too. I love Woody Allen, but I also love Benny Hill, who was the inspiration for The Man Show. Growing up in Las Vegas, I watched Benny Hill reruns. I remember seeing nudity a couple of times, and electricity ran through me. I would watch 20 hours in a row just to see a little nipple through lingerie.

[Q] Playboy: Were you sexually precocious?

[A] Kimmel: No. But I tried stuff. I read that if you take the meat out of a banana, the peel feels like a vagina. So I'd go to the supermarket with a boner and buy bananas. But it didn't work. They didn't hold together. You have to have a very small penis to fuck a banana.

[Q] Playboy: Do you have any other tips for young jerk-offs?

[A] Kimmel: My advice is, stick to the basics. You can experiment with vacuum cleaners, but a handful of Vaseline is the way to go.

[Q] Playboy: You like to denigrate your sex life with lines like "I haven't had a blow job since 1985." That's shtick, isn't it?

[A] Kimmel: It's not. I'm separated from my wife, and that's part of it. We got married really young and somewhere along the line, something happened. Her sexual attraction for me was not there. And it made me very resentful.

[Q] Playboy: You were the only TV star who wasn't getting any?

[A] Kimmel: I won't say sex was the main issue in our separation. I was just taking stock of my life. I was turning 34 and thinking, Is this what I want for the next 40 years? It wasn't. I was a bystander in my own life.

[Q] Playboy: Your kids, Katie and Kevin, are still in grade school. How have they handled the separation?

[A] Kimmel: They were upset for about 12 hours. But I bought a house in the same neighborhood, down the block from the old house. And my Man Show partner, Adam Carolla, told me something very wise and simple. He said, "Listen, the kids are going to be upset. Get a swimming pool." So I did, and my kids can't wait to come over. They love the pool.

[Q] Playboy: After the kids go home, you're not doing without female companionship, are you?

[A] Kimmel: Oh yes, I am. But I'm not lonesome. I'm busy. I work until midnight every night. Anyway, I was practically celibate for the last 15 years. You get used to it. Having sex twice a month is not hard to replace with masturbation.

[Q] Playboy: You were really celibate for weeks at a time?

[A] Kimmel: Absolutely. But I don't want to blame my wife. She wasn't happy, either. I'm really a pain in the ass to live with. I'm very driven and it manifests itself as hostility.

[Q] Playboy: Now you work and watch TV?

[A] Kimmel: I have a 100-inch television and I watch Letterman every night. I love Curb Your Enthusiasm, too. And I watch The Man Show. Adam Carolla is the funniest person I know.

[Q] Playboy: He says you'll be the successor to Letterman and Leno.

[A] Kimmel: Adam and I are deeply in love. It's a shame we're not gay.

[Q] Playboy: Do you have a gay side?

[A] Kimmel: I would never have gay sex, but Adam and I are always looking at each other and going, "This is so gay." When we go on trips, we sleep in the same hotel room. In the same bed. One time we're in this shitty motel in Seattle and I have to masturbate. So I say, "Adam, I need to take a shit." I go into the bathroom and fire one off in the tub. Then he goes in to take a shower. Ten minutes later I hear a scream. Adam was basically attacked by a clump of my sperm. You know, if that stuff's on the wall and you bump into it, it will grab onto your body hair and won't let go! I laughed about that for an hour.

[Q] Playboy: Let's switch from sperm to other manly things. What about earrings? Should a guy wear one?

[A] Kimmel: Never. Earrings on guys are ridiculous.

[Q] Playboy: Harrison Ford has one.

[A] Kimmel: He should be ashamed. He's an 86-year-old man! Did Calista Flockhart tell him it's cool? If I saw Harrison Ford, I would stick my pinkie through that thing and yank it out of his ear.

[Q] Playboy: Let's talk football—do NFL players like you?

[A] Kimmel: Mainly the young ones. Last year I wanted to tape a bit with the Patriots. Tom Brady said he'd love to do it. But Drew Bledsoe was like, "Fuck you." Bledsoe could not have been a bigger prick. I was glad he didn't play in the Super Bowl. He got his karma. But I like Brady, and Kurt Warner, too. I used to goof on Warner for being a Jesus freak, but he is a genuinely nice person. Not like Cris Carter with his Jesus stuff. Carter is a self-absorbed piece of shit who couldn't give a crap about anybody.

[Q] Playboy: Which other reps need some trashing?

[A] Kimmel: Jason Sehorn seems like a phony. Michael Strahan got mad at me because I joked about his mystery sack "of Brett Favre last year. But here's the thing—Strahan had no choice. If the guy lies down for you, you sack him.

[Q] Playboy: Favre shouldn't have done it. That sack set the league record.

[A] Kimmel: As wrong as it was, it was a cool thing to do. And it fucked up Mark Gastineau, who used to have the record and who is a fucking lunatic.

[Q] Playboy: Sometimes Terry Bradshaw, Cris Collinsworth and Howie Long, the Fox football guys, really seem to hate you.

[A] Kimmel: They get seriously mad. The fact is, I can get the better of those guys, and they're bullies. If we were in high school together they'd pick me up and twist my nipples and shove me into a wall. They'd give me a wedgie and snap me in the ass with a towel.

[Q] Playboy: Not Collinsworth.

[A] Kimmel: Yes he would. He's a big, strong guy. You don't get to the NFL being a wimp. Howie Long has a head like a great dane and he's built like a panther. Guys like that are not used to being made fun of. Howie threatened to beat me up, and he wasn't kidding. He threatened to beat up my producer, too.

[Q] Playboy: Did you think that Howie might pummel you?

[A] Kimmel: Absolutely. But he probably won't—he's smart enough to know he'd get sued. This is a tough guy who's used to settling scores on the field. It's hard for him to sit there and take it from some fat comedian he could crush.

[Q] Playboy: Did you like Dennis Miller on Monday Night Football?

[A] Kimmel: I thought hiring him was a ballsy, interesting thing to do. He despises me because I goof on him and he's an egomaniac, but if he's smart he will read these words and pay attention:

[Q] Playboy: He started spouting stats, sounding like an analyst.

[A] Kimmel: I don't give a shit what he knows about football. Funny people are a lot more rare dian smart ones.

[Q] Playboy: Give us a personal stat. You once said that you have a small penis, but you've also said it's anywhere from 19 inches to half the size of Toronto's CN Tower.

[A] Kimmel: OK, OK. It's somewhere between 19 inches and the CN Tower. I have an above-average-size penis for a white person.

[Q] Playboy: And how about your friend Carson Daly?

[A] Kimmel: It's hysterical you mention that. He was at my house two nights ago, and I said, "Carson, a publicist told a friend of mine that you have a huge penis." He said, "Really?" He hadn't heard.

[Q] Playboy: Is it true?

[A] Kimmel: I haven't seen Carson's penis, but I'm saying yes because he's a friend. Everybody says David Duchovny has a huge penis. He was on the radio with me when a woman called in and mentioned it; he got really mad. I said, "Come on. Who are you kidding, pretending to be angry?" I pray every night there'll be a rumor about my penis.

[Q] Playboy: Now there will be. We know it's above average.

[A] Kimmel: Please tell everyone.

[Q] Playboy: How much above average?

[A] Kimmel: I heard 5.4 inches is average, so I'll say 20 percent above. And while we're on penises, did you know that if you're an organ donor, they make your flesh into rolls and sell them to penis surgeons? This was on 60 Minutes. Burn victims can't get skin because plastic surgeons are paying a premium for it. Now, I'm an organ donor, and this troubles me. I want my eyeballs to go to the kid in the car accident, but I don't need a couple of guys banging each other in the ass with my skin.

[Q] Playboy: You had a penis operation, didn't you?

[A] Kimmel: I had three operations on my urethra. It was too small—the opening, not the penis. It's pretty rare. They had to slice it open to make it bigger, but it healed back to the same small size. I had two more operations and it's still not right. I used to pee with deadly accuracy from 40 feet. Now my aim is terrible. The other day at work I peed all over myself. Not just a few spots, so I could say, "Oh, the water splashed on me." It was everywhere. I had to announce to my staff that I'd peed on myself.

[Q] Playboy: You're a medical wreck.

[A] Kimmel: One time I was having sex with my wife and got this horrible headache. I felt like Bruce Banner hulking out. Next day, I'm in my office masturbating and it happens again. Turns out that it's called HDO, headache during orgasm. It happens to guys in their 30s. You get it for about two weeks, then it goes away. I had a CAT scan and they said there was nothing wrong.

[Q] Playboy: How did your brain look on the scan?

[A] Kimmel: They didn't show me. I'd like to see it, though. I love stuff like that. I would pay $20,000 to see a mountain of all the shits I've ever taken. Is that crazy? I'd also like to see a stack of all the pizzas I've eaten. I figured this out once—it's something like 1500.

[Q] Playboy: A minute ago you said, "I was masturbating in my office" as if it's the most natural thing in the world.

[A] Kimmel: I do it every night.

[Q] Playboy: How So?

[A] Kimmel: With my hand on my penis. I'll watch soft porn on cable or look at pictures on the Internet.

[Q] Playboy: You don't have an office shower. What's your receptacle?

[A] Kimmel: The whole room. It's my own masturbatorium.

[Q] Playboy: What does the maid think of her duties?

[A] Kimmel: I clean up after myself. It's funny—I'll freely discuss this in a magazine millions of people will read, yet if my maid found one tissue I would die of embarrassment.

[Q] Playboy: You're shy.

[A] Kimmel: And, fortunately, she can't read English.

[Q] Playboy: Women hated The Man Show, didn't they?

[A] Kimmel: No. Our audience was 38 percent female. Older women might have hated The Man Show, but younger ones knew we were kidding.

[Q] Playboy: Why the difference?

[A] Kimmel: Younger women don't feel as oppressed. They feel like they could be president if they wanted.

[Q] Playboy: Tony Fox, a Comedy Central spokesman, said there could be a post-Kimmel Man Show with a female host.

[A] Kimmel: I officially declare Tony Fox an idiot.

[Q] Playboy: What if it were Roseanne?

[A] Kimmel: No way. They put a female host on Win Ben Stein's Money and drove the show into the toilet.

[Q] Playboy: One priceless Man Show segment was "Household Hints From Adult Film Stars." What was the best hint?

[A] Kimmel: Jenna Jameson getting tarnish off a candlestick. She's rubbing white cream, baking soda and water up and down this phallic candlestick. She really did get it clean. It was sexy.

[Q] Playboy: Why isn't porn better?

[A] Kimmel: Because it's fake. They're acting. What I like is when some guy and his girlfriend film themselves and then it winds up on the Internet. Amateur sex videos—there's a site called Morpheus that's good for that.

[Q] Playboy: Why do men think lesbian sex is exciting, but women don't want to see men having sex?

[A] Kimmel: Because two men having sex is (continued on page 138)Jimmy Kimmel(continued from page 62) really disgusting.

[Q] Playboy: Why?

[A] Kimmel: Penetration, I guess. With women it's just rubbing and touching. When girls dabble in lesbian sex it's more like foreplay, not real sex.

[Q] Playboy: How did Ron Jeremy ever become a porn star?

[A] Kimmel: That shows you who runs porn. Could some fat, hairy broad be a big porn star? No way—there's no Rhonda Jeremy.

[Q] Playboy: Will there be sex talk on your ABC show, or is that taboo on network television?

[A] Kimmel: I hope it's not taboo, because it's every other sentence out of my mouth.

[Q] Playboy: Got any porn stories?

[A] Kimmel: My first was Deep Throat. Before I saw that, I had tried masturbating but nothing happened. I had a boner but I didn't know why or what to do with it. Then, watching Deep Throat, it was "Oh! That's how it works!" My cousin Sal——

[Q] Playboy: Sal Iacono—he replaced you on Win Ben Stein's Money.

[A] Kimmel: Right. Sal is a huge Cowboys fan, so his porno choice was Debbie Does Dallas. He watched it so many times in college that he didn't need the pictures anymore; he could visualize the whole thing from the soundtrack. He taped the soundtrack and then masturbated to an audiocassette.

[Q] Playboy: You grew up in Las Vegas. Were you born there?

[A] Kimmel: No, Brooklyn. But when my uncle retired from the NYPD, he moved to Vegas. Then my grandparents moved there, and when I was nine we did, too. My father had asthma and no job, so it made sense.

[Q] Playboy: You were poor?

[A] Kimmel: We had no money. I wore glasses in junior high, and when one arm broke off, I kept wearing them. For two years I wore one-armed glasses.

[Q] Playboy: Would you say that the Kimmel home was a strict one?

[A] Kimmel: A Catholic one. There was no talk of sex. My mother's got a great sense of humor, but she's uptight. If she sensed that I had a crush on a girl, she would make fun of me. It stunted me a little, I think.

[Q] Playboy: Did you ever sneak into Vegas casinos?

[A] Kimmel: We didn't have to sneak. It was the Eighties—they didn't hassle you for being underage. My friends and I ate the two-dollar steak dinner at the Horseshoe every night. That's where we'd be at four in the morning. One summer I ate at the Horseshoe 39 nights in a row.

[Q] Playboy: In high school you were up at four a.m.?

[A] Kimmel: My friend Cleto and I—Cleto Escobedo, he's the bandleader on my show—would watch Letterman and then go out carousing. We would drive the Strip, hosing down tourists with a fire extinguisher.

[Q] Playboy: Did the tourists chase you?

[A] Kimmel: Oh yeah. We even got arrested. Handcuffed.

[Q] Playboy: Did you say your uncle was a cop?

[A] Kimmel: What's funny is that my other uncle was visiting from New York and we talked him into going with us. This was like the thousandth time we'd done it and the only time we got busted. Cops pulled us over and said, "How old are you?" I said, "Seventeen." Cleto said, "Eighteen." Uncle Vinnie said, "Uh, 44."

[Q] Playboy: Did you gamble, too?

[A] Kimmel: A little. But when I was about 13 my father said to me, "Look around this beautiful casino. How do you think they built all this-from people winning?" After that I looked around casinos and thought, Suckers. They're all suckers.

[Q] Playboy: You're no sucker at football betting. What's your record picking games for Fox?

[A] Kimmel: I average about 70 percent and pick an upset every week. We're not allowed to mention the spread. Television is puritanical about that—they pretend people don't gamble on football when that's why half the people watch.

[Q] Playboy: Do you crunch the numbers, go over injury reports?

[A] Kimmel: No, my cousin Sal helps me with my picks. But there's a lot of luck. In every office pool there's a secretary who wins because she bases her picks on which animal would win: "A seahawk is just a bird. I think lions would definitely beat seahawks."

[Q] Playboy: You have a colorful family—you, cousin Sal and your uncles.

[A] Kimmel: And my dad was a bowling hustler. He dropped out of high school to bowl and win bets. My parents met in a bowling alley. But I'm not a good bowler. I'll bowl a 135 and then, as I get drunker, go down to 109 and then bowl a 64 from my seat. My dad was great, though. He averaged 200-plus. But bowlers in Brooklyn figured it out: "Don't bet with this guy!" He joined the Army, and when that didn't work out he had two jobs. He'd go to work as a short-order cook at five a.m., then work the rest of the day at Equitable Insurance.

[Q] Playboy: What's he doing now?

[A] Kimmel: Vice president of IBM.

[Q] Playboy: You're joking.

[A] Klmmel: No, he is. They've got a million vice presidents, and my dad is one of them. Although he didn't graduate from high school, he worked and did OK. He even bought me a car for my high school graduation. An Isuzu I-Mark. He comes home that day and says, "It was a great deal, so I got one for myself, too." I said, "Did you have to get the same color?" He bought two identical silver I-Marks. I could never tell which was which.

[Q] Playboy: You could check the license plate.

[A] Kimmel: Mine was L8nite, for the Letterman show. So then my dad got one, too: L8night.

[Q] Playboy: You really are Dave's number one fan.

[A] Kimmel: It would freak him out to know this, but to me he's like family. Like my uncle. When he had his heart surgery, I was beside myself. I have a lifelike mask of his head in my office. I guess they made it for the show. Somebody gave it to me. It disturbs me because it looks like he's dead.

[Q] Playboy: Growing up in Las Vegas, did you go to stage shows?

[A] Kimmel: My first one was Sammy Davis Jr., and he was great. Then I saw Siegfried and Roy. They're terrible, but there was a highlight: The elephants on the stage urinated on a bunch of Asian businessmen in the front row. Elephants urinate like fire hoses, so these guys ended up soaked with elephant piss. My whole family about died laughing.

[Q] Playboy: We hear you lost your virginity in a casino parking lot.

[A] Kimmel: My mother will be horrified if she reads this. Yeah—it was with a woman I worked with. I was 17. She was married. She'd caught her husband cheating on her and I was the vengeance.

[Q] Playboy: Where were you?

[A] Kimmel: The parking lot of the Continental, a really shitty hotel. In my Isuzu. I had a 12-pack of Heineken and trouble in mind. And it was unpleasant. I mean, she was nice, she was attractive, but I was too innocent. I was drunk, she was drunk. I was like, "Oh, are we in love?" I never even came. About a month later we checked into a seedy motel and had sex one more time, and that was it.

[Q] Playboy: Was it better the second time?

[A] Kimmel: Better, but not good.

[Q] Playboy: How old was she?

[A] Kimmel: Maybe 25. She had a kid, too. And while we were having sex I said, "Is this your first time?" She laughed, and then she stopped. "Oh my goodness," she says. "Is this your first time?" I said, "Yeah." After that I told a friend of mine I had bad news—I had tried sex and didn't like it.

[Q] Playboy: That is bad news.

[A] Kimmel: Time to rethink the priest thing.

[Q] Playboy: You considered being Father Jimmy?

[A] Kimmel: I was an altar boy for seven years. Every altar boy thinks about becoming a priest, because you're 12 and you admire those guys. I'm still friends with our parish priest in Las Vegas. I said to him, "Father Bill, I keep reading about those altar boys being molested by priests. What's wrong with me? Wasn't I attractive enough for you?"

I do think there's a problem with the Catholic church. People raised Catholic can be raised very strictly and think homosexuality is a sin. Now, if a young guy thinks that but feels he might be homosexual, he might decide the best way out is to be asexual. Not to have sex. He'll think, I can be a priest and I'll be safe. I'll avoid these urges I have. You'll notice the stories are hardly ever about priests molesting young girls—it's homosexuality and trying to avoid it. If priests could get married, more deeply religious people would become priests and the problem would all but go away.

[Q] Playboy: Instead of the seminary, you got into radio. Why?

[A] Kimmel: I read the Playboy Interview with David Letterman. I remember being shocked that he cursed and talked about smoking pot. But he also said he started in radio. So that's what I wanted to do. Pretty soon a guy walks into where I was working—working, but mostly screwing around—and he says, "I'm with the UNLV radio station. I think you'd be funny on radio." I was still in high school, but I went to meet the program director. He's famous now. Ken Jordan—he's in the band Crystal Method. But then he was just a stoned student running the college radio station. He asked what I could do and I said, "Make fun of people."

[Q] Playboy: What was your first paying radio job?

[A] Kimmel: Morning radio in Seattle. I got $20,000. It was supposed to be $30,000, but after I moved to Seattle for the job and got my first paycheck, it didn't add up. I go to the general manager: "You said you'd pay me 30," He says, "No, I didn't." Asshole! I'm 20 years old, married for six months and my partner and my wife and I all live together to save money. One day the program director says, "Guys, I got it. 'Jokes for Doughnuts!' People call in with jokes and you give them doughnuts." And I said, "That is the stupidest thing I ever heard." I got fired.

[Q] Playboy: How did you feel?

[A] Kimmel: Small. My wife and I went back home and moved in with my parents. They were glad to have me back, but they couldn't really deal with me as a married adult. I was out of work for 10 months before my partner Kent—he's still one of my writers—and I got a show in Tampa. Did that for nine months and got fired. People laugh about how I kept getting fired, but it wasn't funny at the time. I was shocked and felt worthless. Finally, I managed to get my own show in Palm Springs, California, a tiny market. Carson Daly was my intern.

[Q] Playboy: He worked for nothing?

[A] Kimmel: For a long time he made nothing. Then I paid him $25 a week out of my money so he could eat lunch.

[Q] Playboy: Is that about what you pay your victims on Crank Yankers? The Man Show is over for you, but you're still making prank calls with puppets on Comedy Central.

[A] Kimmel: People don't get paid for Crank Yankers. They get T-shirts. Most of them think it's cool to be on the show.

[Q] Playboy: But you make fun of them.

[A] Kimmel: Mostly we say nonsensical stuff, and they have to deal with it because they're at work. Like calling Spago. "Bill Cosby is coming," I said, "so the restaurant must be at an exact temperature." The bathroom had to be sealed off for Bill's use only. No one was to make eye contact with him—they all had to look at the floor. "If you refer to Bill," I said, "you have to call him 'my man.' And there can be no square food. If he sees square food he'll go crazy." I said he'd want chopsticks. They don't have chopsticks at Spago, but they said they would get some black chopsticks from the Chinese restaurant next door. "Absolutely not! Bill would call that a racist slight."

[Q] Playboy: Who's next on your hit list?

[A] Kimmel: I just did one for next season, posing as Tommy Lee's assistant. I'm calling a hotel, saying, "You'll need doctors on hand because Tommy will probably OD. And he'll smash all the windows."

[Q] Playboy: Will Tommy be a good sport about that?

[A] Kimmel: He has no say in it.

[Q] Playboy: So, who is worse, Oprah or Rosie?

[A] Kimmel: I'm not an Oprah fan. At one point she was great, but now she thinks she's a prophet. Rosie O'Donnell is 100 times worse, though, because she's a hypocrite. She's known as the queen of nice, but this is the most notoriously unpleasant person in show business. She picks easy targets like Joan Rivers, who is 10 times funnier than Rosie ever was. And my executive producer used to be Rosie's executive producer, so I know how terrible she is.

[Q] Playboy: You play in celebrity golf events. Tell us a good golf joke.

[A] Kimmel: There aren't any. But I'll unhook the other guy's golf bag so it flies off the cart, and I'll pee on his golf balls.

[Q] Playboy: You don't really pee on guys' balls.

[A] Kimmel: I do. Who's going to arrest me? This is part of my job.

[Q] Playboy: You were a square on Hollywood Squares.

[A] Kimmel: Worst day of my life. Adam and I got a bad square, like the middle top, and they cut all our jokes. We were too dirty. But there was a highlight: Robert Schimmel, who is one of my favorite comics, was on that day. He decided that to amuse us, every joke he told would be about Louie Anderson eating ice cream out of a man's ass. There was a story about Louie paying a male prostitute for the privilege. It can't be true, but it's funny. So on Hollywood Squares, whenever they called on Robert he talked about Louie Anderson eating ice cream from a guy's ass. Of course it didn't make the show. They cut it all.

[Q] Playboy: You hosted a Friars Club roast of Hugh Hefner and introduced him with the line, "I can't say anything about Hef that hasn't already been mumbled incoherently by a girl with his dick in her mouth."

[A] Kimmel: Some of the best stuff was cut from the TV version. Dick Gregory gave this serious, awful speech, and all the white people stood up and applauded out of white guilt. Now I have to follow that and be funny. So there's a beat, everyone sits down and I say, "So the other day I'm jerking off and I got my pinkie all the way up my ass." They loved it, but it was too dirty for TV.

[Q] Playboy: You roasted Shaquille O'Neal as well.

[A] Kimmel: Queen Latifah told a story about how Shaq dared his cousin to take a shit on the stage during Latifah's show. Said he'd give him $50,000 to do it. Then, when Shaq went on Letterman, he offered the cousin $250,000 to come up and shit on the stage. If I had a zillion dollars, that's how I'd want to spend it.

[Q] Playboy: Shaq's cousin didn't do it, though.

[A] Kimmel: My cousin Sal would do it for free. When we were in high school Sal shit in a bag of Fritos and marched into a 7-Eleven demanding his money back. "Look in this bag!" he said.

[Q] Playboy: Did he get his money back?

[A] Kimmel: He got a new bag of Fritos out of it.

[Q] Playboy: Was it at all tough to recruit Juggies for The Man Show?

[A] Kimmel: No. Hollywood is filled with all these homecoming queens from every small town in America. When you are the most popular girl in school, there's only one way to maintain that level of attention: You have to get famous. Hollywood is a whole town of those girls. Most of them go through their lives unsatisfied.

[Q] Playboy: They become Juggies.

[A] Kimmel: Hey, the Juggies loved their work.

[Q] Playboy: Does it help their résumés? "I was a Juggy on The Man Show."

[A] Kimmel: Their résumés are great. The skills—we auditioned one girl who put "rappelling" on her résumé. Another one said she could do an Irish accent, but all she could say was "O'Malley."

[Q] Playboy: Your kids have been on The Man Show. What did they think of the Juggies?

[A] Kimmel: They were on the show, but I never let them watch it. It's a dirty show. They're not sophisticated enough to get the subtleties of what Daddy is doing.

[Q] Playboy: They'd think Daddy was just glaring at Juggies?

[A] Kimmel: Exactly. Which Daddy is, but he wants to convince them otherwise.

[Q] Playboy: How about a race—

[A] Kimmel: White. I'm white.

[Q] Playboy: No, a sperm race that you and Adam had.

[A] Kimmel: We went to a sperm bank and raced to see who could get the sample out first. Adam won with something like two minutes and 10 seconds. I was 2:17. Then I reached up and put my hand on his face. Is that the gayest thing? That might be gayer than the shower.

[Q] Playboy: The Jackass staff did a sperm race, too.

[A] Kimmel: I have much better sperm than Johnny Knoxville.

[Q] Playboy: There was talk of a movie with you and Adam.

[A] Kimmel: We wrote one that's called Hot for Teacher, but the Hollywood community doesn't feel we're important enough to star in it. Several studios offered to buy the script, though, for somebody else to be in.

[Q] Playboy: Who?

[A] Kimmel: Johnny Knoxville. MTV Films said they would buy it for him. It's like something out of The Player. It's a joke—a guy electrocutes his nipples and now he's a movie star.

[Q] Playboy:The New York Times thinks you're important. The press has said you have "the attitude of Conan O'Brien without the Harvard underpinnings."

[A] Kimmel: I don't know what an underpinning is. But Conan's funny. I could be a writer on his show, I think. But all those writers from that Harvard Lampoon comedy factory, most of them go on to write bad sitcoms and make no contribution to comedy. They're so smart that they pepper their work with pop-culture references that are kind of funny-sounding but are not actually funny. My aunt Chippy—a cantankerous, hilarious 60-year-old from Brooklyn—could cut those guys to ribbons.

[Q] Playboy: Is Howard Stern funny?

[A] Kimmel: Funny and smart. People who say he's stupid haven't heard his show.

[Q] Playboy: Doesn't he pander to the lowest common denominator?

[A] Kimmel: Sometimes.

[Q] Playboy: Do you?

[A] Kimmel: Never intentionally. I'm not denying that a lot of guys watched The Man Show for the boobs and the masturbation jokes, but those are the herbs and spices, not the meat. It's like The Simpsons. When my kids watch The Simpsons, they crack up when Homer shows his butt. And I do, too, but I crack up because on every show he shows his butt.

[Q] Playboy: To you, his butt's funny on a meta level.

[A] Kimmel: Last year on The Man Show, Adam says, "It's like my friend's father used to say: 'Excuses are like assholes—everyone has one.'" He was making fun of how trite that is. But the audience goes, "Woo!" Adam says, "No, you idiots, that's not the joke." That's when I thought, OK, we're done with this show.

[Q] Playboy: Time for the talk show.

[A] Kimmel: Time to move on.

[Q] Playboy: Do fans of The Man Show send you stuff?

[A] Kimmel: T-shirts with dumb slogans. One said Emerson Bigguns, which of course sounds like, Them are some big ones. If you shot me in the head and put that shirt on my corpse, I would tear it off in the grave. I do get some good stuff now, like three free sets of Titleist golf clubs, but it's hard to enjoy it. This is my real problem: not enjoying anything. When you're poor you would kill for a free pair of sneakers. Then suddenly you're a millionaire and it's, "Geez, I don't care now. I could buy all this stuff."

[Q] Playboy: Do you have any hobbies?

[A] Kimmel: Just masturbation. Hobbies are mostly for women. Adam Carolla flies remote-control airplanes like a retard. When I retire, though, I'd like to go the Red Skelton route—make some horrible clown paintings and get a gallery to hang them because I'm famous.

[Q] Playboy: Do you vote?

[A] Kimmel: Yes. Democrat, usually. I wanted Al Gore to win, but I'm OK with Bush. I didn't like him until I heard what a lunatic he was in college. Maybe he won because of a fuckup with the ballot in Florida, but I don't think the Republicans planned it. It was an accident. What we should do is change the rules so that the guy with the most total votes wins. The Electoral College is crazy. Just count the votes! And while you're at it, simplify taxes. Right now, as we speak, I've got accountants poring over the tax rules. They'll come to me and say, "We're declaring your car as livestock." Just take a percentage of my salary.

[Q] Playboy: President Bush will be a great source of jokes for your new show.

[A] Kimmel: No, I'll let everyone else bore the life out of young people with George Bush jokes. Fucking Jay Leno is still doing Clinton blow job jokes! Can't we move on already?

[Q] Playboy: Got any Kimmel blow job jokes? What's your career total?

[A] Kimmel: My life total of blow jobs? Well, what counts as a blow job? Does it count if she is just getting it wet for a minute before sex? No, OK, that's foreplay. So my estimated total is 20. Twenty blow jobs. And when you're 35 years old, that's not so good.

[Q] Playboy: That's got to change, doesn't it?

[A] Kimmel: I'm not asking you to do anything about it.

[Q] Playboy: Last question: Now that you're a star for Disney, ABC's parent company, do you get Disney perks?

[A] Kimmel: When I was on the Ben Stein show they set me up for tickets at Disneyland. So I go there and say, "Tickets for Jimmy Kimmel, please." And they say, "Who?" There are no tickets. They blew it completely. But I'm guessing that will change. The next time they promise me Disney perks, there will be Disney perks. They won't want me cursing Disneyland on their own channel.

[Q] Playboy: Maybe you'll get to sleep with Pocahontas.

[A] Kimmel: I'd go more for Betty Rubble. Nice, big feet. More accessible. Betty's more my speed.

I was practically celibate for the last 15 years. Having sex twice a month is not hard to replace with masturbation.

Dennis Miller's problem is that he thinks it's more important to show how smart he is than how funny he is.