Jen Kirkman loves Madonna, enjoys talking about Madonna and has been known to wear Madonna-themed clothing on stage, but make no mistake, she is not Madonna.

A man made that mistake recently and the mixup turned one of Kirkman’s sold-out New York City shows into a show that all of sudden had 30 empty seats. Purchasing 30 tickets to anything would seem to be a commitment worth investigating fully, but not for this guy.

Apparently, he ponied up for 30 tickets just on the off chance that Kirkman’s “All New Material, Girl” tour was merely a front for some special unplugged Madonna concert featuring songs from the pop icon’s “Like A Virgin” album.

It wasn’t, and although the title of Kirkman’s tour confused at least one person, she said during a Monday morning interview that the idea behind the tour name was to eliminate confusion about what her fans will see at each stop.

In her own words, “I’ve got new material for you, girl (and boy).”

Kirkman, a brilliantly funny stand-up comedian who returns to North Carolina on Nov. 1 for a show at Durham’s Carolina Theatre, has two outstanding Netflix specials, is a New York Times best-selling author of two books and is one of the best stand-up comedians I’ve ever seen in 20-plus years of attending comedy shows.

Getting to interview Kirkman again was a treat and an honor and in the first installment of this two-part interview, we discussed Madonna, of course, Bernie Bros, what can and can’t be blamed on Generation Xers like Kirkman and myself and more.

Enjoy the interview, follow Kirkman on Twitter and don’t forget The Best Tweet I Can Find in Five Minutes at the end.

Tony Castleberry: We spoke extensively about Madonna the last time I interviewed you, so let me start this interview by saying the name of your tour, “All New Material, Girl” is great. Did you come up with the name?

Jen Kirkman: I did come up with the name. I love that you think the name is so good that I might have had a team working on it.

TC: [laughs] I imagine a bunch of writers in a room and one of them goes, “I’ve got an idea” and they just sprung it on you. Is that how it happened?

JK: Pretty much, and they’re unpaid writers so they do things like come up with the name of my tour. They’re just lucky to be there. [interviewer laughs] I have a funny, quick story if you can handle anymore Madonna talk.

TC: Always.

JK: I named this tour so that people would be very clear that this is not anything they’ve seen on Netflix. I wanted to get it out of the way in the title.

So I did a gig in New York City and it sold out, and then not, because the last second, at the door, a guy who had 30 tickets was getting a refund because he was like, “Wait, this isn’t Madonna?” That’s what he thought he was going to see.

TC: Are you kidding me?

JK: You know how Jerry Seinfeld’s (Netflix) special was him doing old stuff? I think the guy thought it was that, Madonna doing “Material Girl.”

First of all, not that she wouldn’t do a small, intimate night, but why would she do it under the name Jen Kirkman? [interviewer laughs] If you want, put in your article that this is Jen Kirkman.

TC: This isn’t a Madonna, aka Jen Kirkman situation. This is actually Jen Kirkman.

JK: Yes.

TC: Perfect. What is your approach to new material? Do you do a new hour each year?

JK: The new hour each year thing is hard to guarantee. I try to have new material each time I tour, whether that be a year or two years, but I don’t force myself. I don’t want to ever repeat material to audiences who might think, “Oh, she’s doing the same thing over and over.”

I took a year off of touring just because I’d been touring so much. I thought, let me rest my voice and also just, I don’t want people getting too used to me. Let’s build some excitement.

Usually when I’m on tour, I have like a set hour, but I might work out 10 minutes of new stuff here and there so by the end of the tour I am actually into my next new hour, if that makes sense. This time I had nowhere to do that (since I wasn’t touring) so I had a show in Los Angeles where, one night a month, I would get onstage and just babble for an hour off the top of my head. The audience knew what it was. They were very supportive. I did a whole new thing, which is just try to make stuff up so that’s how I did it. If I feel passionate about topics, I’ll talk about them, but I don’t force anything.

This tour is new material to (the fans) but it’s been workshopped already. The stuff’s less than a year old.

TC: If you don’t want to talk about this, I understand because I know you deal with it daily on Twitter, but were you surprised by the trolling or straight up online harassment you got from Bernie Sanders supporters?

JK: The first time it happened, yeah, but that was a long time ago, like a year and a half ago.

I was surprised because I was a big supporter of his for many years and then when I decided that I wanted to support Hillary (Clinton), it was a lot of harassment. It was very interesting. As we now know, I was encountering those paid Russian trolls, which of course I sound insane saying. You would think his supporters would go, “See? We’re not like that. Aren’t you glad it wasn’t us?” Yet they’re still having trouble digesting that (the Russians played a role in the latest presidential election). It’s very strange. I think he fired up a lot of 90s young people that are just looking for a fight, a revolution, a something and I think the way they think they should go about it is to trash the other….well, not the other side. The same side, different opponent.

It’s very strange how people fell for all of the talking points about how different (Sanders and Clinton) were and how dangerous she was. I was just in Canada and there were still people saying to me, “Ya know, Trump is awful, but he’s only a little bit worse than she was.” I was like, “Oh my God. What’s happening?”

TC: This is gonna sound like the whitest white man thing ever said to you probably, but I meet a bunch of college friends one week each summer to play golf and this year, we mistakenly got into a discussion about politics one night and my best friend asked another friend what he thought about Trump. This guy, who I’ve known for a long time, replied, “He’s the lesser of two evils.” I was floored. That type of mentality seems to permeate and it persists, which is maybe even a little bit scarier than the thought itself, don’t you think?

JK: I think so. I mean, obviously there are always undercurrents of sexism, but it really is affecting disinformation. I think that’s the new kind of war we’re in. Somebody put it very simply. I heard it on a political talk show that, Russia doesn’t have an economy. They don’t have a big military so this is how they fight now. I guess it sounds crazy and I guess that’s to their advantage, that anyone who is saying there is a disinformation war, people start making the crazy person gesture. “There’s a crazy person over there.”

My friend who has teenage kids said, “As wrong as these people who are harassing people are, you’re only surprised it happened to you, Jen, because you don’t have teenage kids.” She’s not recommending I go get them, but she’s practiced in the world of young people telling her, “You’re stupid. I’m more liberal than you. I know how to change the world. You dumb old lady. You guys got it wrong.” That type of thing. I was told by young people online that this isn’t even a woman-man thing. It’s a young person to older person thing. I was told that because my generation was slackers, that’s why we have global warming.

TC: Wow.

JK: I was like, “Guys, we certainly didn’t stop it, but we did not start that one.”

TC: You can’t put that totally on us.

JK: Somebody was like, “If you guys weren’t busy slacking all the time…” I was like, “All right. It isn’t that literal.’”

Another favorite harassment I got during the election was, someone asked me if I had college debt. I said no. They said, “See, you don’t relate to us because college was free when you went.” Honey, I don’t have college debt because I’m 43 and I paid it off within 25 years. [Kirkman, interviewer laugh] That’s the reason I don’t have debt. It wasn’t like we walked into a one-room schoolhouse in 1992 and just read books for free. I had a lot of debt. I’ve just been around a long time. I’m not saying (college debt) is good, but again, you guys aren’t the first.

Here it is, The Best Tweet I Can Find in Five Minutes:


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