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.