Comedian Kathleen Madigan doesn’t like to overthink things. In fact, the 49-year-old Missouri native is content just being on the road 300 nights a year, performing standup everywhere from Detroit to Dallas, Charleston to Escondido.
“I run into so many comedians who get nervous and they overthink everything,” Madigan told Folio Weekly during a recent phone interview. “And I’m, like, ‘Look. Are you doing what you want to do? Are you making enough money to pay your bills? Then shut up, because most people aren’t. Be happy. Why can’t you be happy?'”
She’s been at it for 25 years, even earning the distinction of being “the funniest comic in America, bar none,” from good friend and fellow comedian Lewis Black. She’s also won the American Comedy Award for “Best Female Comedian” and the Phyllis Diller Award for “Best Female Comedian.”
Raised in a large Irish Catholic family, most of Madigan’s standup act is based on situational humor — specifically, making fun of her relatives, from her mom mistakenly dosing her with blood pressure medication instead of Advil, to her brother homeschooling his four kids.
“I think there are some unnecessary things that are said just to cause shock. I don’t really do that and it’s because I don’t like confrontation,” Madigan says. “So, for me, I wouldn’t say anything that would hurt my family’s feelings. I make fun of my family a lot, but it’s all within a context that’s all facts.”
Madigan’s comedy career began in the 1990s, and it was entirely by accident: While she was working at a St. Louis bar that she also frequented as a patron, the bar’s owner declared employees could no longer drink there after their shifts.
“So I went to the bar across the street, which happened to be a comedy club,” Madigan remembers. “They would have open mic nights and we would just do it for fun. Eventually, somebody paid me $50 and I was, like, ‘Wow! That was easy for $50.’ It was really about the money, honestly. And I don’t mean that in a greedy way. I mean that in a ‘how am I going to make a living?’ way.”
Two-and-a-half decades later, Madigan’s been on just about every late night show, from the Late Show With David Letterman to Conan to The Tonight Show with Jay Leno. She’s also done several specials for Comedy Central, HBO, Showtime and most recently Madigan Again, which premiered on Netflix in September.
But Madigan’s true love is crisscrossing the United States showcasing her standup shtick — light on improv and carefully constructed beforehand.
“Most of it’s worked out because I feel like people are paying a decent amount of money [to see me],” she says. “They’re probably getting a babysitter, they’re paying for parking. I would expect the performer to be prepared. So that’s what I’m doing because I would expect that of myself or anyone I went to see.”
Madigan expects that same kind of preparation from others. In fact, when Folio Weekly placed a (punctual) call to the comedian, she spent the first two-and-a-half minutes of the interview talking about how journalists are always late. (Editor’s note: She is so very right.)
“Especially since I’m the comedian, I’m supposed to be the fucked-up one, right? Isn’t it supposed to be the musician and the comedian that really can’t get it together?” Madigan says. “The talent is the one who’s supposed to be a mess, who’s supposed to be hungover.”
Aside from being really funny, perhaps one of the reasons Madigan’s found so much success as a comedian is that she treats it like a business. She’s literally been on the road for 25 years and hasn’t stayed in one spot for more than three weeks at a time.
“It’s been completely organic,” Madigan says of her lengthy career. “And the one thing is, I’ve never been a big overthinker. I’m pretty much always thinking, ‘OK, this is what I’m doing today. This can all go to crap tomorrow, I guess.’ And then I’d have to figure something else out.”
Asked what she’d do if it did all go to crap, Madigan doesn’t hesitate. “Well, I like talking to people. I like bars and I like sports. So I’d open up a bar. I would be happy doing that.”