Jessica Michelle Singleton isn’t afraid to go there. The comedian, who audiences may recognize from Hulu’s Iliza’s Locals—a showcase curated by comedy powerhouse Iliza Shlesinger—has built her brand on fearless self-deprecation, breakneck pacing, and turning life’s darker corners into something disarmingly funny. Ahead of her upcoming show at Hilarities Fourth Street Theatre in Cleveland on March 20, she caught up with CleveRock.com to talk about her wild comedic voice, life in the spotlight, and why she’s glad trolls can’t keep her down.
When asked how she defines her comedic style, Jessica doesn’t hesitate: it’s “a little dark, a little dirty, very fast paced, and off the cuff.” She thrives on unpredictability, often talking about her family, her fiancé, and the absurdity of modern life. “I wouldn’t say I’m political,” she explained, “but I kind of talk about observational life—and some of that will venture into dark and maybe like joking about mental health and how we need to figure that out. You’re going to hear me making fun of myself a lot. I do a lot of talking about my family. Currently, the situation I’m in is that I’m engaged, so there will be jokes about that whole situation. I joke about the state of society. I wouldn’t say I’m political. So if you’re looking for Daily Show pundit style comedy, I’m not for you, but I kind of talk about observational life and some of that will venture into dark and maybe like joking about mental health and how we need to figure that out.””
And while Hilarities lists her show as “Rated R,” that rating only tells part of the story. “My show is still objectively rated R,” Jessica admitted, laughing, “but I used to be a lot more heavy about some dirty, dirty material.
Whether she’s riffing on her own awkward moments or diving into emotional territory, Jessica’s magic is her ability to lighten up heavy subjects. “I take a lot of dark topics and I make them wildly lighter than you would think someone could,” she said. “It’s a way to find levity in the chaos and the heaviness that sometimes is day-to-day life.”
That sense of realness runs through everything she says onstage. When asked how much truth fuels her material, she was quick to laugh. “I would love to have things that aren’t so insane happen that I could take more artistic license,” Jessica said. “But if you come to a show for me, I think 99.9% of what you hear me say is going to be a hundred percent accurate. There’s some comedians who can really run away with a story and add a bunch to it. For better or worse, I usually don’t have to add much. It’s just chaos around me that I am observing at all times.”
If Jessica seems in total command of her career, that’s because she’s learned how to make the business work for her. Her most recent comedy special, Hi Y’all, debuted straight to YouTube—an intentional move that’s helping her cut past gatekeepers and reach new fans. “The most wonderful thing about YouTube is there is no gatekeeper,” she said. “People who already know me are going to find it, but now I’m getting new fans every day… it’s free, and my comedy is for working-class people. I just pop up on their sidebar. There’s so many people now that YouTube’s their TV, and it’s free, so you’re not cutting anyone out. My comedy is for working class people. When I come on the road, when I go to Cleveland, this is a night out. People spent their hard earned money and that’s not lost on me.”
Of course, the open internet also means open season for trolls—especially for female comics. “Honestly, it’s some of the most mentally ill things you’ve ever seen,” Jessica said. “The dirty material especially, the trolls will come out of the woodwork, but I realized their mean ‘women aren’t funny’ comments boost the post anyway.” She laughs off the hate now, leaning on her fans to fight the comment battles for her. “It’s astounding. They’d never say it to your face—it’s always a picture of a truck!”
In the heart of all her punchlines is a deeper goal: giving people a break from the madness of life. “At the end of the day, that’s what I do. When I have a show, we’re taking an hour and a half and we’re not thinking about our boss, or the news,” Jessica said. “It’s so much of it you can’t even control. It is crazy. So this is a way to check out and for one moment in your week, you go, ‘I’m not thinking about what’s going on in my personal life. I’m not thinking about the bad things in the world. I’m laughing at this lunatic who’s running around the stage, screaming about her fiance.’ You leave and you go, ‘Wow, thank goodness I took a break from doom.’”
And she can’t wait to deliver that comedic escape to Cleveland once again. “I can’t wait to be back,” Jessica said. “It’s been a couple years and I love Cleveland. I love [Hilarities’ owner] Nick [Kostis]—he runs such a great operation. The food is upstairs, the club’s downstairs, it’s incredible. It truly is one of the most magical comedy clubs in the country.”
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