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7 Questions With: Bailey Pope

7 Questions With: Bailey Pope

There’s an interesting throughline between performing in punk bands and doing stand-up comedy. Todd Barry and Fred Armisen are two prime examples of artists who made that leap — and it makes sense. Both forms of entertainment require a certain fearlessness and drive to challenge the status quo. And at their best, punk rock and stand-up are about speaking truth to power, often with raw honesty and a sharp edge.

Brooklyn-based comedian Bailey Pope is part of that lineage. Like many before her, she transitioned from music to comedy, carrying over the DIY ethos she absorbed in the punk scenes of her youth. Alongside fellow comic Sasha von Didkovsky, she co-hosts Fun Gutter, a monthly Brooklyn stand-up showcase that pairs comedy with live music. The show has featured performances from such underground comedy heavyweights as Chris Gethard, Jo Firestone, and Judah Friedlander.

Ahead of her headlining set at the LaZoom Room on Friday, April 25, Pope took part in Asheville Stages’ 7 Questions with Comedians series.

Jonny Leather: What makes you laugh?

Bailey Pope: I love uncomfortable or awkward situations. I don’t think anyone is cool all the time, and when awkward situations happen, it’s the most authentic moments we get. The best laughs in any situation come from real-life building tension [with] laughter being our only release. 

JL: How do you handle a joke bombing on stage?

BP: Please refer to question #1. Bombing can happen to anyone anytime, but my work grew exponentially when I realized that I’m not the only one uncomfortable during a bomb. The audience is often just as uncomfortable. Sometimes just acknowledging that something didn’t work helps release the tension for everyone, which unites the comic and audience. 

JL: Is there a comedy special, set, or specific traumatizing event that made you want to do stand-up?

BP: I grew up on punk rock and hardcore. I was in bands but was always enamored by stand-up comics. I saw them as doing the same thing while also being more authentic in a way by sharing about their lives. As a trans woman and knowing I felt off about my gender from the time I was six [years old], I’ve always valued being able to authentically share and connect with others because I spent most of my life hiding a lot of myself from others. Comedy, to me, is a perfect way of bridging a gap to others who might not understand queer identities and can benefit from a snarky, irreverent, tattooed trans woman teeing it up in a different way. 

JL: Is there a moment at which you realized that you could do stand-up professionally?

BP: In my day job as a hairstylist who presents as an educator from a product company, I used humor in my work and would constantly be told I should try standup. My canned response, for years, was, “I respect stand-up too much to get involved.” It eventually ate away at me, and I took a stand-up class which gave me a sort of permission [that] I was seeking to feel ready for an open mic. I had two margaritas before my first set, didn’t eat shit, and fell in love instantly. 

JL: When heckled, do you: a) Eviscerate them; b) Breakdown / curl up into a ball; c) Just feel grateful someone showed up for your set?

BP: If you ask any of my friends, they’ll tell you that I roast because I care. With that said, I pride myself on being able to control any unwanted interaction without it derailing the show. I’m often surprised at how little I get heckled as I often perform in smaller towns or areas that don’t support trans folks. When it does happen, I like to remember that the audience is also being heckled because they didn’t ask for Joe Bob to pipe up. So, I work to protect the audience from being cheated out of a good time, however necessary.

JL: What’s the best part about being on the road?

BP: I love being on the road. I use Atlas Obscura to find oddities/monuments/ruins/etc., to break up the drive. Then I love finding the bar where locals and, specifically, where the service industry gather at the end of the night. That’s the real shit in every town.

JL: Why should the people of Asheville catch your upcoming set?

BP: Face-to-face connection is more important than ever. My comedy is about having fun while hearing a perspective that you might not have heard before. I’m often the first trans person many people have actually met, and they often realize misconceptions that they had. Laughing together is one of my favorite things in life and is one of the best ways to build community and bridge gaps. 

IF YOU GO

Who: Bailey Pope
When: Friday, April 25, 8:30 p.m.
Where: LaZoom Room, 76 Biltmore Ave., modelfacecomedy.com
Tickets: $15 advance, $18 day of show

(Photo by John Cafaro)

Through the Lens: Color Me Asheville by Goodwill 2025

Through the Lens: Color Me Asheville by Goodwill 2025