The Contenders: Jimmy Kimmel’s dogged pursuit

He killed at the White House Correspondents’ Dinner. His late-night talk show has never been better. And he’s hosting the Emmys in September. It’s good to be Jimmy Kimmel … unless you’re Jimmy Kimmel. He explains why in a recent conversation at his Hollywood office.

You said the White House Correspondents’ Dinner was the second most terrifying night of your life. What do you remember about the most terrifying night — your first appearance on Letterman?

I had 17 pages of things to talk about. I had a tattoo of Dave drawn on my chest. And I got bumped.

You must have been crushed.

No. I was relieved. My agents and publicists were annoyed, but I couldn’t have been happier.

You were invited back. You had six months to hone those 17 pages.

Six months? I had been planning what I was going to say to Dave if I ever met him since I was 16 years old.

And you fulfilled that ambition.

That’s the thing. If I had been voted anything in high school, which I wasn’t, it would have been “Most Likely to Watch David Letterman.�

Not “Most Likely to Appear on Letterman�?

We didn’t think like that. I never made the leap from “show� to “business.� I didn’t think there were little men inside the TV, but it wasn’t too far from that.

Ten years in, what do you remember about your show’s early days?

It was complete chaos. I had no idea it was chaos. I assumed this is what every show was like. But there were many nights when it was 5 o’clock, the show was going live at 9 and we had no guests.

Which explains the frequent appearances of Kathy Griffin, Sarah Silverman …

… Adam Carolla, David Alan Grier, Anthony Anderson. Those were our core emergency guests.

Was it fun, building the show from the ground up?

It was the opposite of fun. I would pray that the show would get canceled. I was downstairs in a windowless office the first two years. The show would end and the staff would just continue drinking and hanging out in the green room until 2 in the morning. I felt like I was the only one working and everyone else was having fun.

But you’re having fun now, right?

I’m still not having fun.

Really? The Correspondents’ Dinner, hosting the Emmys, the show’s doing great …

None of it is fun. They’re all hurdles that must be cleared. I put a lot of pressure on myself, and I torment everyone around me until those hurdles are cleared. I have a hard time enjoying myself in general. I really do. I have trouble relaxing.

You’re vacationing next week in Yosemite. Can you relax then?

Even when I’m relaxing, I’m not relaxing. I told my girlfriend this morning that I have some stupid T-shirt ideas that I want to make. I have a list of things I need to accomplish on my vacation.

Soon you’ll have to focus on the Emmys.

The truth of the matter is, most people in the audience just want to know if they won or not. That’s their No. 1, 2, 3 and 4 concern. And once they’ve won or lost, they want to get the hell out of there. By the end of the show, you’re just talking to a bunch of seat-fillers.

You had Oprah Winfrey on your post-Oscars show this year, and I have to tell you, it really felt like a betrayal to our gender.

[Laughs] I guess you could look at it like that. The way I look at it is Oprah had every reason to despise me and she was gracious enough not just to participate but jump in all the way.

No kidding. She jumped into a bathtub for one of the sketches.

That was here in my disgusting bathroom. You want to see it? [We walk to Kimmel’s office bathroom. It isn’t exactly disgusting, but it’s hard to picture Winfrey soaking in the nondescript beige tub.]

You got Oprah in that?

When I heard we were shooting it here, it was like, “You guys, we have to clean this thing!� And I went crazy, tearing things out, trying to clean it up.

It’s not every day that Oprah visits your bathroom.

And when she does, you should probably have some nice soaps out.

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