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Jon: Well, being small and Jewish is a good recipe for developing a wit. Most of my laughs came from my classmates.

Marlo: So you were the class clown.

Jon: Actually, my friend was voted class clown. I was voted best sense of humor. And I take great pride in that distinction.

Marlo: You should.

Jon: I did. My fart humor back then was very sophisticated. I did top-notch stuff. But what passes as wit when you’re younger is really just obnoxiousness. Then you slowly learn the difference between something that will make people laugh and something that will get your ass kicked. There’s a very fine line there.

But, yeah, the stories of my childhood lack any real magic. I was very much like a bad ABC Afterschool Special. Latchkey kid, basically unsupervised, most of the time thinking up ways to entertain my friends. It all feels so clichéd. Even the way my family got divorced. My dad got laid off and then had an affair with a secretary. It was Philip Roth, you know?

Marlo: Conan O’Brien told me that he spent his entire childhood making fun of himself so nobody else would.

Jon: That’s exactly right. If you had the best Jew joke in town, or the best short joke in town, at a certain point nobody wanted to compete with you. I mean, my last name is Leibowitz. Just about every fun curse word for a little kid rhymes with that. “Tits.” “Shits.” So unless you could top the other kids material-wise, they’d be relentless.

Marlo: Did you have a couple of standard lines that you defended yourself with?

Jon: No, it was all situational. We didn’t write stuff back then. It wasn’t the Orpheum Circuit. But you did have to be quick on your feet. In some respects, that was good training for stand-up comedy, because it’s all in the moment. You’re just trying to deflect things.

Marlo: You do that a lot on your show.

Jon: Yeah. In some ways I think you’re always the kid you were when puberty first destroyed your life. That sense of esteem you were searching for is always a part of you, no matter what happens. I remember my life before I got on television, and how much harder it was to get laid then. So believe me, I have a decent sense of my own self-worth.

Marlo: Maybe you weren’t getting laid, but you were always getting laughs.

Jon: Yeah, well I gotta tell you, getting laughs was cold comfort to getting laid. The one thing I can remember from high school was that being the funny guy got you access to the party, but typically in some sort of advisory or service role.

Marlo: Meaning?

Jon: Meaning, the first time I got to second base with a girl, I was actually driving and watching my friend do it.

Marlo: Really?

Jon: Yes—that was the first time I saw a breast: as my better-looking friend felt someone up in the back of my Gremlin while I drove.

Marlo: That’s hysterical.

Jon: But I was a great lure. Have you ever seen the old angler fish lure? It’s got that weird little thing coming out of its head. That was me. I would do the dance and draw in the people. Then they would come in and say, “Wow. Now, can we go fuck your friends?”

Marlo: Ah, so you were the pimp, really.

Jon: That’s right. Or the carnival barker. You sort of bring people in for the ride, and then they say, “Oh, you’re so funny. Now . . . is there anyone we can actually go out with?”

Marlo: You mention being the only Jew on the block. When I was growing up, all the best comedians were Jews. But look around now: There’s Letterman, Colbert, Leno, O’Brien. You’re the only Jew.

Jon: But that’s always been the case on a national platform. You know, the Jews were the tummlers, they were the guys in the clubs battling it out. But when it came to national TV, they wanted the guy from Nebraska. They wanted Johnny Carson, not Joey Bishop.

Marlo: So how did you sneak through?

Jon: Basic cable, baby! The world changed when basic cable came around, and suddenly you didn’t have to appeal to the widest swath of people anymore.

Marlo: You know, my dad was Lebanese, which made him an unusual looking choice to play a father on prime-time