A 25-year veteran of standup, Kathleen Madigan may be one of the most consistently great storytellers in comedy. Her third standup special, Madigan Again, premiered earlier this month on Netflix and will be available for download later this the year. She can also be seen on The Late Show with David Letterman next Friday, Sept. 27. I got the chance to talk to her over the phone recently about getting invited over to people’s houses, not knowing real jokes, and why she and Lewis Black have never been in the cool kids’ club.

How do you approach putting together a new special? Do you set out with a focus for the new hour, or is it just where your material is when you decide to record?

It’s where I am, but I wouldn’t do it if I didn’t feel like it was a really solid new hour. Like, I could have a new hour, but is it worth a special? It usually takes me about two years to write a new hour. And then people are like, “Oh, it takes too long.” Well, maybe it’s because I care. [Laughs] How ‘bout that? I mean, I could pay writers to write me jokes, and I could stand there and just babble on if all that was required. But I’d rather it actually mean something to me. I just do it my way and it takes a little bit longer than if I paid people to write for me. But I’m fine with that.

I’m always so impressed by how seamlessly your shows flow - it really feels like just one long story. Do you develop it in that style, or do you just develop individual stories that you weave together?

The transitions just sort of appear. It really sort of does it on its own. I mean, I have to go on stage every night and do it, but the transitions become apparent. I’m not writing stuff on purpose to fit a transition, but things happen and then the transitions just make themselves clear. My act seems to go in chunks, and it’s always like the same four, maybe five chunks, which would be traveling, my family, politics, current events, and sport if any sports are really jumping out, like Olympic years. But it’s usually the same types, because that’s really what I’m interested in in life.

Some guy wrote on Twitter – this is a really good complement, he said, “Saw your show, it was really awesome. It felt like you were in my living room.” And that’s exactly how I want it feel. If you said to me, “Hey, what have you been up to?” and I haven’t seen you in two years, “Oh my God, here’s what happened. I went to Afghanistan.” It’s more like a bar conversation than it is cold jokes. Because when people go, “Tell me a joke.” I’m like, “Seriously, I don’t know any jokes.” Unless you want to do the knock-knock jokes I do with my nieces. They watched the special and they were very disappointed I didn’t do any knock-knock jokes. Especially the ones they taught me. I said, “Well, you’ll have to wait until I do an all knock-knock special.”

The show really does just feel like a conversation, and your voice on stage is so authentic, like it’s really you and you’ve made it work in a standup setting.

This is why, when I get off stage, people just invite me to their house. They don’t know what I’m really like. They happen to be right. I really am exactly like my act, so it would be fine if you asked me over to your house. I would be totally normal and have some beers and then go home.

There’s just some people that just exist to be funny, and can tell a good story. Sometimes I think it’s like, can you sing or not? I can’t sing; there’s just no amount of lessons on Earth. What are you gonna do? Some people just aren’t funny. There’s nothing you can do. It’s innate. I don’t even think about it, at all. And other comics will say, “You write a lot.” I don’t really write anything. I wait for things to happen and then I tell you about them.

Since you’re on tour pretty much all the time, do you just work in new material to your shows as you go?

Yeah. Some of comics, after they do a special, they just dump that hour and go to little clubs and try to start over. I don’t even think that people necessarily want that. Like, there’s been a lot of retweets and quotes about some of those Afghanistan jokes [in the special]. So I think people want to hear them. I would never do the same exact hour. I just go, “Okay, I’m sick of talking about all this political stuff. It’s over, no one cares about Mitt Romney anymore.” So that will just go back in a notebook and now, that empty five minutes, I have to fill with something. But there’s always stuff in my head. I drop chunks, I don’t drop a whole act. So if you see me on the road, it will always be new and old. And either way, people are gonna complain. If you do all old stuff, people are gonna complain. If you do all new stuff, people are gonna complain. So the only compromise I can think of is, new and old. For the most part, that seems to keep everybody, including myself, happy.

And Lewis Black is featured in the special. I feel like, so often, when I see one of you, I see the other.

He really is my best friend.

Do you work together a lot?

We try. We really can’t do that many shows together. We have to do weird things together. Like, he did a comedy cruise, so I took off and went on that, or we’ll do charity stuff or golf tournaments. Or for his special in Atlantic City, I took off that weekend to go. I didn’t work but just to hang out, be around, and he came to Detroit and was my opener for 15 minutes. And I said, “I will give you the greatest hotel room.” It’s just fun. He doesn’t need me to buy his hotel room, but you just need to be come and be off for three days and watch me work and then you don’t have to do anything. And that’s what we’d both rather be doing, is not working.

Do you think you’ve influenced each other’s standup?

I don’t know. He’s always had his thing and I’ve always mine. We both can write for one another, which is weird, because we’re nothing alike. But we can see what the other one’s doing. But usually, we’re just goofing off. We talk about work, just so we know what’s going on, but I think we’re kind of over it. Maybe we’re just old crazy people riding around in a golf cart.

It’s funny, because in comedy, I think of there being all these little groups and cliques in different cities and scenes, and you two seem to be in a little comedy bubble of your own.

We are. We are not the cool kids. We will never be the cool kids. There’s definitely a cool kid clique; we are not in it. [Laughs] We do not care. We’ve always been the outside. And we’re not sure why. We’re really nice people. But neither he nor I have any interest in going to a Hollywood party. We have no interest in showing up for the things where all the cool people are gonna be. If anything, we would actively avoid it, which is probably why we are not in the club. But we’d rather go watch football somewhere and have some wine. There’s nothing about show business, other than the actual work, that we’re interested in.

And you both have really strong followings. It’s like you’ve cleared your own paths rather than going through someone else’s system.

The systems never really work out for us, and even when you tried to play to nice, they’re just jackasses. And you go, I don’t want to do this anymore with this clique, so I’m out. And then we just kind of float on the perimeter. But like, I’m really good friends with Ron White, and the blue collar guys were never accepted by any other comics or cool kids. They’re doing their own thing too. It’s a completely different thing than Lew or I would go after, but we kind created our own little forrest too.

And those guys have such a fanbase too. It’s a reminder that there are lot of people unimpressed with whatever’s cool in LA or New York.

Yeah. Everybody’s forgetting about the rest. I’m doing the Mirage next weekend in Las Vegas, and you look at the list of the Mirage headliners, and it’s the people that aren’t in the cool kid club. Because the cool kid club, it changes about once every three years. There’s no staying power. So I really hope if you’re in the cool kids club, you enjoy your time in it, because it will not last. The staying power is in having real people, not show business people, like what you do. And that’s why I don’t understand what the younger comics – who’s gonna be playing the Mirage 20 years from now? None of you even have an hour. You don’t even have 20 great minutes. So, it’s just bizarre to me. Even, like, Daniel Tosh headlines it. And he’s on Comedy Central and he’s got a fanbase, but he’s kind of an outsider too. He lives at the beach, he surfs. He doesn’t do the thing, run around and be part of the scene.

And I think there’s a tendency on the coasts to think that people always on the road aren’t doing stuff that’s as smart of clever as the city stuff.

I think they always think that if you’re popular, you must be hacky. And that’s not at all the case. I mean, was George Carlin a hack? A lot of it is disgruntled city comics, sitting in crappy clubs, saying that the road isn’t worth it and the road is stupid because they didn’t do well on the road. So then you go back to the city and you can tell your inside, pseudo-intellectual jokes to the six people, and they’re cool if they laugh. It’s like this chain of insanity. What does it turn out to be in the end? What is the point of all this? I don’t really see one. They do view the outsiders as maybe not as smart, or hacky. I don’t know what the words are, but it’s definitely not positive. [Laughs] I’ve seen a lot of comics [and thought], “You’re really smart, but it wasn’t funny.” I mean, people paid. I think that’s my Midwest mentality. People paid, and the agreement was, I’m gonna make you laugh. That’s what I’m getting paid to do. So to be self-indulgent, I find that to be rude. I’ve seen it a million times, and I’m like, “You’re just gonna use this stage as your basement?” To me, no. There’s people here, they paid. You made an agreement.

But if you went up at UCB in New York, you would still do well, because funny is funny. 

Funny is funny. Exactly. That’s why, some of the city clubs, I’m actually really glad that I don’t have to do anymore. Because, to sit in the back and watch what passes as funny, no. No. No one’s laughng. You can sit here and say it was a smart joke, it was a well-written joke, or blah blah blah. But the bottom line is, it is instant results. Do they laugh or not? Is every crowd stupid? I find that hard to believe. Every once and awhile you can say, “Not a great crowd.” But you still have to do it. That’s what you get paid for. It’s just unbelievable to me that people keep blaming the crowd or this or that. Well, whatever. It’s like playing sports and blaming the wind. Yeah, learn how to play in the wind.

Kathleen Madigan: Madigan Again is available now on Netflix. The CD and audio download will be available Oct. 8, and the DVD and video download on Dec. 10. She is on Twitter at @kathleenmadigan.

Elise Czajkowski is an Associate Editor at Splitsider. She should really tweet more.

Photo credit:  Natalie Brasington

Talking to Kathleen Madigan About Her New Standup […]