Headshot of Ashley Gavin, a white woman with long brown hair. She wears a backward baseball cap, a burgundy short-sleeved top, and dark trousers with sneakers. She is also wearing a necklace. In the photo, she is smiling with her hands on her knees, seated on a flight of stairs painted white, with the paint somewhat worn away.
Ashley Gavin Credit: Jim McCambridge

Brooklynite and professional ballbuster Ashley Gavin has a nickname among her fans: “Mommy.” Or, as rudely shouted by one lady in the audience last week, “asshole.” She’s technically neither, but as a nationally touring stand-up and host of the comedy podcast We’re Having Gay Sex, that hasn’t stopped her from cultivating a significant following of queer and straight listeners who are drawn to her wit, frank conversations, and crowd work. I talked to Gavin ahead of her residency and special taping at the Den about operating at one’s high limit, maintaining a career in today’s evolving comedy industry, and an unexpected city for finding some damn good Ethiopian food. This interview has been edited for length and clarity.

Dan Jakes: At this point in the tour, how are you feeling?

Ashley Gavin: I’m always tired. [Laughs]. I wish I had a better answer than that. I’m just getting used to it. It’s all very new, so I’m just learning what my capacity is. I’m past it for sure. Hopefully I’ll figure out how to scale back.

All these dates, these are real road dog numbers. 

Yeah, they’re definitely road dog numbers. And I hope people know I’m so excited about it. I realize in text it might come off as I’m exhausted and I can’t handle the work! But, no, it’s super exciting. It’s interesting because comedy isn’t the same as music touring. It’s sort of a never-ending experience.

At this point in your career and this point in the pandemic, what is your relationship with travel like? 

I love going to different cities. I’m always trying to do something weird or interesting in a city that I’ve never been to before. I find that it gives me a lot of energy. But I haven’t figured out how to use the plane rides economically.

Outside of some of the major comedy hubs that everybody thinks of, have there been any cities with unexpectedly good vibes? 

I’ve been loving the midwest. My shows in the midwest have been some of my favorites. That’s why I chose Chicago to tape the special. And I love the Den. I just thought it was a really cool space. And I had the best Ethiopian food ever in Omaha.

Ashley Gavin
2/23-2/26: Thu-Sat 7:15 and 9:30 PM, Sun 6 and 8:15 PM, Den Theatre, 1331 N. Milwaukee, 773-697-3830, thedentheatre.com, $21-$51

You’ve talked about the adjustment that it’s been for audiences to get reacclimated to being a live audience. I’ve noticed it at plays, movie theaters, and comedy clubs for sure. What’s happening?

Oh God, I don’t know. I’m really glad that you’ve noticed it, too. Like, audiences are gaslighting me. I’m like, “You guys are not OK.” And they’re like, “What are you talking about?!” [Laughs]. It’s been weird going back. We really became much more online as a society. And so people are kind of struggling a little bit with some etiquette and social cues. Also, a lot of my audience is younger, and so they’ve never even seen live comedy. They’re young adults that are really experiencing social life, and nightlife, and stuff like that for the first time as adults, because the pandemic pushed back that basic life experience for them. And they’re learning, in real time, what being a good comedy audience means. People are not sure of how loud they’re allowed to laugh. Or they’ll respond in a studio audience way, where they’ll woo or aww or groan. And I’m like damn, this is so weird! I just want you guys to laugh!

What are some of the benefits and challenges of performing to a largely queer audience? 

I think with any comedy show, diversity of thought and experience is really important, because people laugh at different things. So it can be an adjustment to have—not that everyone isn’t a special little snowflake [Laughs]—but you know, people [can be] pretty similar, so they laugh at similar things. That can result in more extremes. The sections that do well with that crowd do super well. And the sections that are a little bit more foreign, they take more time to adjust to hearing that kind of joke.

I think also, my audience isn’t just queer; they’re also new to comedy, and they are young. They want to be good people. I feel like Gen Z is really trying to change the world in a way we haven’t really totally seen since like the hippie era, you know? They are not used to hearing dark humor from a lesbian. Usually it takes ten to 15 minutes, and then they’re on board and it’s totally fine. But those early ten to 15 minutes are very interesting because I’m literally explaining to them that they can laugh at all of these things, that I’m not going to take some offensive turn. Like, if they hear me speak about race or class or gender, that I’m not going to pull the rug out from them.

There’s a difference between comics poking fun at or challenging their own communities versus folks like Roseanne Barr telling pronoun jokes to an audience chomping after red meat.

Right, exactly. I don’t know if Sarah Silverman coined this term, but she calls it a “blood laugh,” when you’re telling an ironic or satirical joke that maybe has that edgy quality to it, but ultimately, underneath it all, actually has the opposite point of view. She can hear the difference between people who really understand what she’s saying and people who want to laugh at the joke for the wrong reason. People say you can’t tell a joke anymore. That’s not really true. You just need your audience to understand your point of view. Then you can go bananas. We have a lot of trust issues in America right now. [Laughs]. You kind of have to let them know that they are safe.

Your brand of roasting isn’t full-on “mean,” either. Is it more accurate to call you a ballbuster? 

Yeah, ballbusting is not a bad description of it. I feel like the way that I am onstage is the way comedians are with their friends. It’s a form of intimacy to be at that level with somebody. In all of my best friendships and relationships, there’s a lot of roasting going on. I think people find it empowering in a weird way. I think it’s nice for them to see a woman be able to be angry and have it not be a negative thing. It doesn’t have to be threatening or off-putting for a woman to be a little angry the way that, like, Bill Burr can kind of get a little angry. 

It’s fun seeing straight people loosen up on your podcast. I feel like there’s something liberating for them to talk to queer people about relationships. 

Totally. They have a lot of rules. [Laughs]. And they don’t have to follow all of them.

A lot of the comics that I’ve spoken to, especially the longer-form storytellers, have had such an existential crisis over TikTok. It seems like you really have been able to embrace it and not lose the true stand-up nature of your work.

Thank you for saying that. I don’t put my material on social media, and I don’t put it on there because it’s too precious to me. Some of my bits are like ten minutes long. I’m going to cut that down to 45 seconds? It just doesn’t feel like the best representation of my stand-up, especially because of the way the algorithm works. And I’m very lucky as a comedian that I enjoy crowd work, because I’m able to get that hook. I think I’m just lucky that I enjoy crowd work at the moment where crowd work is going super viral. 

How’ve you been feeling about your growing list of business responsibilities on top of your artistic work? 

I’m fortunate that I like business. I will say I’m at a weird in-between point where I feel like I finally have name-brand recognition, which is incredible. But when you’re at the early end of that, you’re still doing a lot of business management. It’s really hard in terms of just work-life balance. And also, you want the people who work for you to feel valued. 

It’s like, “Oh my God. Like, how successful should I be right now? Am I spending too much?” Because we’re comedians. We have no fucking idea what the margins are supposed to be. You don’t know what your cost of a new customer is. You have no idea. That’s probably the scariest part, like, “Am I doing a good job?” Not with the comedy, with the business. Am I doing any of this right? And you can’t really ask anybody that. No one really knows.

You have a very distinct sense of fashion. 

I don’t know whether that’s a compliment, but I’m gonna read it as that. 

How would you describe your sense of style? 

I would say, like, a middle-school fuckboi. A teenage boy who realized that if he paints his nails, the girls are into that.

Patreon and social media monetization seem to have changed the game for how comics make money, right at the time when residuals and lucrative commercial gigs are thinning out. Are we getting to a point where stand-up can be the thing without having to have the peripherals as well?

I never thought about it that way, you’re right. Stand-ups used to need a writing job or a role in something. A commercial. You can replace that with a Patreon. My Patreon is enormous for my career. Enormous. And every month, I panic about whether or not I’m going to lose everybody. You have to make a real investment in all of your free content. And what people don’t realize is, like, that one-minute clip took a trip to another city, an hour-long performance, all of the prep to edit, the edit, and the captioning, and the click-baiting and the putting it online. It’s probably eight to ten hours of work for one clip. So you have to be willing to make that investment in yourself.

And that’s scary for a lot of comedians. And that’s why I think a lot of people would rather have a writing job. But I don’t know. I think it’s worth it. I also think it’s like social media has created a bigger middle-class of comedians. I think it could, anyway. I’ve no data to support that. But I think there’s a lot of comedians who are able to make a solid living because of their small-to-medium following online, whereas before you could not do that.

You’ve been very open about working while experiencing chronic pain. No job is easy when you’re not feeling 100 percent, but your job is so personality-based. How do you work through it? 

I don’t want to toot my own horn, but I feel like, in terms of anything that I do, my work ethic is probably the thing that I would rank as the most above-average. And only in the past year have I reached points where I was like, “Oh, this is capacity. I cannot do more than I’m doing now.” I guess I’m just really lucky that I make my own schedule, because the thing about pain is you just don’t know when it’s going to wreck a day for you. 

So I think I just have to be super mindful about when I’m hitting those times that I actually cancel things. 

You’ve recently mentioned that you’re feeling a new level of satisfaction in your personal life and in your career. Is happiness something that you have to manage?

This is an interesting topic because I wrote a solo show last April about the idea of happiness. I took this course on Coursera from Yale called The Science of Well-Being. I meditate every day. I try to exercise like three times a week. I prioritize sleep over everything. And I make time to spend with my partner and my friends. And I think even though I’m so busy, if I’m able to maintain those things, I’m pretty happy. If I can keep them up, even in the craziest times, I’m at least able to be like, “Holy shit. Like, you’re having a crazy time as a professional comedian!”

Like, I’m able to have gratitude for what’s going on around me rather than being a curmudgeon about it, which I never want to be. Those are the comedians that I’m like, “Fuck you, dude.” Like, you have everything everyone wants, and I understand why it’s so hard to stay happy. But why else are we doing this other than to have this really cool life? So we should enjoy it.