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Judd: Brenner is so funny. I used to watch him on The Mike Douglas Show all the time.

Steve: He actually helped my career quite a bit.

Judd: How so?

Steve: It was ’73 or ’74, and I went to see him somewhere in Washington, D.C. He was really hot at the time, hosting The Tonight Show, with a beautiful girlfriend. I remember after the show, they came out and they were both wearing full-length mink coats. Anyway, I wrote to him. I was living in Santa Fe at the time. I said, “I can’t make any money. I can get paid maybe three hundred dollars for a gig, but it costs me two hundred dollars to get there.” And he writes back and says, “Here’s what I do. I tell the club owner, ‘I’ll take the door, and you can have the bar, and I’ll have a guy stand at the door with a clicker.’ ” I couldn’t, you know, with my WASPy thing, I couldn’t ever say that, but I did ask the club owner to give me the door. That’s when I decided I would only be a headliner—and it changed my career. The opening act doesn’t get any traction and a headliner does.

Judd: How did you arrive at the ideas in your act, early on? I mean, you were taking apart what it means to be a comedian. It was not observational comedy. The act itself was fascinating.

Steve: I was lucky to have come up in that era because today, every area is covered and there’s so many good people. If I was starting now, I’d be lost.

Judd: But no one’s doing the type of comedy you were doing. There are really smart comedians, but there’s not a lot of conceptual comedy out there.

Steve: I think it’s a dead end, you know.

Judd: Because it runs out of gas?

Steve: Yeah.

Judd: You can’t keep doing it?

Steve: I mean, I’m still around, but I couldn’t have kept doing that act, I don’t think.

Judd: You’ve developed a different comic persona now, which feels distantly related to that. When you host the Oscars, I can sense that you’ve redefined your persona.

Steve: Yeah, I have. I didn’t want to do the same old thing and I didn’t want to look like I was doing the same old thing. That extreme physical thing has totally gone out of it. And I love playing the egotistical asshole.

Judd: I’m always fascinated by people’s comic journey—when they get bored and say, That’s enough. There are people like you, who seem to find new things to keep them interested, and there are people who say, I’m just going to hang out at the house. It’s a real challenge because success never satisfies whatever you thought it was going to do for you. You think, Oh, I thought success would heal me and it doesn’t. So you have to look for new reasons to keep making things.

Steve: I read a book in college called Psychoanalysis and the Arts. And it compared Picasso and Chagall. Picasso was a guy who just kept changing his whole life and Chagall essentially painted the same things, over and over. And it talked about there being two types of creative people and I think that applies.

Judd: When you got bored of doing stand-up, was there a part of you that thought, Okay, this next thing will bring me happiness?

Steve: No. I was just beaten down.

Judd: And you feel the joy again, now that you’re out touring and making music?

Steve: I really enjoy doing the shows, but the wear and tear—I have a daughter at home. It gets a little painful.

Judd: When did you start playing the banjo?

Steve: I’ve been playing it for over fifty years now.

Judd: The second I hear that instrument, it makes me feel that happy Disney feeling. I read something where you talked about how fun it was to be creative with something that’s completely nonverbal.

Steve: I think playing the banjo has extended my brain life by another ten years.

Judd: Because it just connects everything?

Steve: Yeah, just thinking in another way.

Judd: Do you feel like this is a common trait, among the people that you’ve chosen as intimate friends? This creative searching? Is this how your friends also deal with this ride?

Steve: Yes.

Judd: Everyone around you seems to have a sense of humor about it, but they’re also working really hard.

Steve: Everybody I know—I’m talking about Tom Hanks, Mike Nichols—

Judd: Lorne.

Steve: Lorne, yeah. Marty. All of us, we know how lucky we are. Everybody says, Oh, God, we have such a nice life, you know. We’re lucky to have had this happen to us.

Judd: Yeah.

Steve: Everybody is grateful.

Photo Insert

My parents, Maury Apatow and Tami Shad, either exhausted at the end of their wedding, or pretending to be. 1964.

Me dressed as Harpo Marx for Halloween. Never been happier. 1975.

With Jay Leno backstage at Rascals Comedy Club in West Orange, New Jersey. 1984.

Interviewing Jerry Seinfeld at his West Hollywood apartment. Notice the lack of decor. 1983.

Me being way less funny than Robin Williams on The Tonight Show with the great Jay Leno.

(Paul Drinkwater, © 2010 NBCUniversal Media, LLC)

Dennis Miller before hosting the Paul Simon Live in Central Park HBO special. Notice my green shorts. 1991.

Steve Allen waits to speak into my gigantic tape recorder. 1983.

Martin Short and me. One of us is aging badly (not Martin). 1984, 2013.

(Photo on right courtesy of Justin Bishop)

This is how comedians dressed on the 1992 HBO Young Comedians Special. (Clockwise from top left: Bill Bellamy, Nick DiPaolo, Judd Apatow, Janeane Garofalo, Andy Kindler, Ray Romano, and Dana Carvey)

(Photo courtesy of Andy Hayt)

A bunch of idiots trying to get stage time at the Improv. (Left to right: Judd Apatow, David Spade, Allen Covert, and Adam Sandler)

(Photo courtesy of Tony Edwards, 1990)

My first gig writing for the HBO special Tom Arnold: The Naked Truth. I now weigh more than Tom. 1991.

(Left to right: Judd Apatow, Tom Arnold, Roseanne Barr, Martin Mull, and Pete Segal)

Traveling with Jim Carrey to London for the Liar Liar press junket. 1997.

Me, Ben Stiller, and “Saul.” 1993.