I was open to the idea of it, but there were many things that had to be worked out first. ABC came to me and said, "This is what we're doing; we want to be sure you're okay with it." I didn't say, "Yeah, I'll follow Jay," but I didn't say I wouldn't. It was scary and kind of exciting. We didn't know what was going to happen.

Was your contract up?

My contract wasn't up, but had Jay Leno come to ABC, my contract would've been up for grabs.

So you have time-slot protection? If they bumped you out of eleven thirty, you could leave?

Yeah, exactly. I had exactly the thing Conan didn't have, and you should have seen my contract when I signed. It was ridiculously terrible. I don't know how he didn't get that. He should kill his lawyers.

Okay, so it's a couple of years later. Jay's about to push Conan off the air. And you decided to go on your show dressed up as Jay Leno. How'd you come up with that?

It came to me at about two o'clock in the morning. I was in bed and I thought, Oh, this would be funny. So I sent an e-mail to everyone saying "Tomorrow night I'm doing the show as Leno. We have to get a chin and all that stuff." It turned out to be a funny thing to do—my bandleader, Cleto [Esco­bedo], was particularly great in the role of Cackling Kevin.

Did Leno call?

Oh yeah. The next day—and I knew Jay was going to call—and I was like, "Oh God. Should I tell him I'm not here and call later? No—then I'm going to suffer all day." So I took the call.

And?

He said it was funny.

Do you think he meant it?

No. I don't think he means anything he says.

What happened next?

I said, "Well, thank you, I'm glad you thought it was funny," and we had a little chat, and that was the end of it. An hour later, they called and asked me to do his show the next day. I was shocked. But I thought if he was going to be a good sport about it, then I should, too. Then I got on the phone with the segment producer, and the questions they were going to ask had nothing to do with what was going on [in late night]. It was just typical dumb stuff.

My memory of those nightly satellite-interview segments is that they were always driven by that kind of thing. "What's your favorite junk food?"

That is correct. There were a lot of questions like that. And as we talked, I slowly realized the goal [of having me on] was to minimize the damage I'd done and show the audience: Jimmy and Jay are buddies. I hadn't talked to Jay forever before that call. I talked to him a lot when he was thinking about coming to ABC, and when he took the job at NBC, I never heard from him again. So I decided I wasn't going to be the jerk that went along with Jay's scripted comedy bit. I was going to talk about it one way or another. So I felt we'd reached a compromise; Jay would talk about his things, and I would talk about mine. It worked out, I guess. [laughs]

Watching it again, there's definitely this split second after he asks you about the best prank you'd ever pulled, where I could almost see you stop and think, "He just handed it to me on a platter." And then you laid into him. I think you said something about promising a guy your job in five years and then just stealing it back. What's going through your head in a moment like that, humiliating someone on his own show?