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If Johnny Carson Could Retire, Why Can’t Kathleen Madigan?

Kathleen Madigan Photo-Illustration: Vulture; Photo: Shutterstock

Kathleen Madigan is an exception. Over the past three decades, comedians just haven’t built and sustained the sort of touring-and-specials business she has without some sort of major TV or movie role. But Madigan, who has been a theater act for years, released her sixth special, Hunting Bigfoot, on Amazon earlier this year almost exclusively from building a fan base on the road. Coming from a long line of Midwestern union workers, the 57-year-old has always approached stand-up as a job, working upwards of 250 nights a year, and by doing so, she has established herself as possibly the most successful road comic ever. Now, as she sees retirement age on the horizon, she’s thinking about what it would look like for a stand-up comedian to hang up the microphone.

On Good One, Madigan talks about working as a road comedian, how boring acting is, and one day ending her never-ending tour. Read some excerpts from the interview below or listen to the full episode of Good One wherever you get your podcasts.

You are arguably one of the — if not the — most successful road comedians ever. You built your audience on the road exclusively. Are you proud of that fact?
I am proud of that, but it was sort of just luck. One time, Lewis Black was on The Big Bang Theory. He played some nutty professor, and he was like, “Will you go with me?” I said “Lew, I’ve been to a sitcom once, and it was so boring. I don’t want to go watch. I love you, but I don’t want to go.” And he was like, “Please?” And I was like, “Fine.” We left my house at four and we got home at 11. Me and his old assistant drank a bottle of Chardonnay throughout the day. We plowed through a bottle. I had memorized the whole script, his parts, the other parts. It’s so slow and tedious.

I just want to tell jokes. There’s not many of us where that’s all we want to do. When I started comedy, as far as I knew, that’s what we all wanted to do. And then it started getting to be Look, Ray Romano’s got a sitcom, and Kevin James has a sitcom. And I’m like, Yeah, but do you know what goes on over there? Do you really want to be that bored for hours upon hours? For what? You’re not even an actor! Like, they offered me some part in some NBC thing not that long ago, within the last five years. And I was like, I’m not an actor. I don’t want to. I kept saying “no,” and they kept offering me more money, and I said, “No, I’m not seeing that as a bargaining trip. I truly want nothing to do with this.” I don’t think the agency was saying it like that. I was like, “You need to tell them I have no interest in TV or movies unless it’s a friend and I get to play myself as a bartender.” I did it for a couple of people twice. It was awful, just like I thought, but I did it as a friend.

There are people that are qualified to act. It’s insulting to call a stand-up comedian, who has had no experience, an “actor.” I’m like, All I want to do is to tell jokes in front of people for an hour. The show’s two hours and I’m done. That’s my workday. I do some other stuff, but I’m in charge of it all. I’m my own boss.

Was it hard to maintain that position when you lived in L.A.? A lot of people have a really hard time resisting the values system of the city. 
Initially, when they told me to go audition for stuff, I’d get pissed off at the gate. I could never get on the lot. I’d be out there for 20 minutes going, “Goddamn it! My name’s on a list!”, trying not to get mad at the person. You have to want what’s at the other end of that gate.

I auditioned for some commercials. I did it like three times, and I was like, The money would be great. Why not? It’ll take three days out of your life. But the odds of you getting that commercial — is it worth a day of your life? I lived in Hermosa Beach. I could be rollerblading right now! If you told me, “Do you want to go fishing?” Yes! “Do you want to go play golf?” Yes! But do I want to go be on a sitcom all this week? No.

You’ll periodically announce a new tour, but it seems like it’s actually all the same never-ending tour.
It’s never ending! People are like, “Oh, so how long has this tour been?” — people who don’t know, like radio people. And I’m like, “35 years so far!” I’m not Black Sabbath; I don’t get to take two years off and think of an album.

It starts when you’re in theaters. Let’s say I do the Chicago Theatre once every 18 months. They don’t want to put the same poster up. They don’t want the same ad. That’s what’s driving all that, and that makes sense. But usually it’s new jokes by the time I get back there. But tour names for comics? I’m just grasping at anything. Call it Box Wine and a Tiny Banjo. I don’t want it to be a title where the press could be mean.

What do you like about this idea of a never-ending tour both personally and creatively?
Well, I just like going around. The first few times I went around, I did all the touristy things. And then you start making friends in those towns, and it’s a chance to see my friends again. If I’m going to go to Columbus, Ohio, I’m not going to the zoo. I’ve been there a bunch. I’m going to go see my friends.

And then, work-wise, me and Ron White have the same theory: You’re either working or you’re not. It’s like going to the gym: “Oh, really? You haven’t been in three months?” I do not know how these stand-up comedians, who I haven’t heard their name in two years, all of a sudden have a special. Really? Where did you do that? That is incomprehensible to me. I’m not saying it’s wrong. I’m not saying they’re not necessarily funny. I just don’t understand.

I have to be in a rhythm. Even if I take a week off, that first show, I’m going to forget a couple of things. It’s just rust. And Ron is such a pot monster that his memory is shot. He’s like, “I can’t remember anything but ten minutes in my whole life!” That’s all he could work up during COVID. And I was like, “Well, that’s enough! You can be my opener!”

He retires, but then just opens for you!
Yeah, why not? Just go out there and do ten minutes! It doesn’t even matter how good it is. I don’t know. I feel like when I quit, I quit. I’ll do charity stuff or something, but when I’m done, I’m done.

Are there drawbacks, personally or creatively, about living on the road like this?
Well, it’s very difficult to have a normal life. Most people will hate you because you’re gone all the time. They think it’s funny in the beginning, and then you miss another baptism and another birthday. But that’s never the life I wanted.

But you can’t have stability. You have to be comfortable with organized chaos. I do really well in organized chaos because it keeps my attention. It’s activity based versus with my one sister, safety would be her No. 1 thing. She wants to be organized, safe, nothing unpredictable. That’s her idea of happiness. Mine is I like it to be very unpredictable. I’d like it to be chaotic, but I want to know I have control over it. I’ve always been like this, even when I was a kid. I think parents would say that too. Like, my one sister, every night before school, she had her uniform set out, her things set out, everything was perfectly organized, neat. My side of the room looked like it had been looted! So I just think I’m meant for the road.

You talk about retirement sometimes. Conceiving retirement is hard for a lot of comedians. Often they’ll be like, “Well, once I do this, maybe I’ll stop,” and then whatever “this” is becomes an ever-increasing idea.
The carrot.

I don’t have a sense that you’re like that, but do you have a sense of what it would feel like to be ready to retire?
Yeah. During COVID I was like, If the world was open, this is wonderful. I had basically turned into my mom and dad but in my 50s, not in my 80s. But I couldn’t quit.

What do you need to quit?
I need my financial-adviser brother to say so. This is what financial advisers do. I would say this in front of his face — they’re a tad bullshit-y. I go, “Pat, how much money do I need to retire comfortably?” And he goes, “Well, that depends on your definition of comfortably, Kathy. Does that mean you’re playing golf at the fancy course that costs $250? Or are you willing to slum it and go over to the $50?” I go, “No, no, no, I’m not talking about all that, Pat!” So when the money’s all right, I know I’m free to go, and then I just have to think, Is there any last thing I want? I don’t think so. I can’t think of anything.

Now that you are in the space considering retirement, are there things that you can be like “These are the things that I’m proud of. These are the things I wanted to do or hoped for my career that I’ve achieved”?
No, because the weird thing is, if you’re anywhere near my age, we didn’t even know those things were gonna exist, so you couldn’t dream of them. What’s HBO? And then it shows up and it’s like, Well, I want to get a special on HBO! But that couldn’t have been a goal because that didn’t exist. Sirius radio didn’t exist. Netflix didn’t exist. Amazon Prime didn’t exist. Nothing. It’s all been a “wing it” thing. I think actors could say the ultimate thing is an Academy Award or a SAG Award. We don’t even have any of that. So it’s like the Joy of Painting guy: There’s no problems; there’s just happy accidents. If you only want to tell jokes, and that’s what you care about, and you’ve done all the specials that you think you are done with, is there anything I’m forgetting about?

You were able to do both Leno and Letterman, which is not a thing a lot of comedians are able to say they did.
Yeah, I was pretty proud of that because my act was just balanced enough that I had stuff weird enough for Letterman but mainstream enough for Leno. Their sets were very, very different. It’s hard to even picture both in one. But, even now, I could take that hour on Amazon Prime and go, Okay, this is what I’d do if I had to do it on Leno. I’d do all the jokes about my mom and dad because that’s Middle America. And then I’d do the weirder Bigfoot thing for Letterman.

Are there things you hope to be able to get better at at this point? Is there something about the craft of it that you think about?
Nope, and I never have. I mean, I wish I had better answers. The beginning was the hardest, hardest, hardest part, and then after what, I don’t know, five years maybe, you know what you’re doing; you’re not nervous like crazy. I really know that I know what I’m doing now, so venue size, I don’t really care. I don’t even want to do an arena. The more I talk about things like this, I think I treat this like a job.

Johnny Carson retired and nobody said, “Hey, what’s wrong with you?” You’d see him occasionally at Wimbledon; they’d always show him. He loved tennis, so you’d see him as a fan. He did what normal Midwest people do: When they’re 65 years old, they retire. I’m good! I’ll have to think about that. Is there anything left? Now you’ve made me have to think about it because I haven’t thought about it! Is there anything left? No, because even the places that I want to go I can just go on my own. I don’t need to book a show there.

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If Johnny Carson Could Retire, Why Can’t Kathleen Madigan?