The comedian's 'Bad Listener' offers both a fuller portrait of the artist and a lesson on better engaging with one another

For Nickey Winkelman, the easiest part of putting together “Bad Listener,” her debut one-woman show, was assembling the mannequin with which she'll share the stage.

The nameless figure — Winkelman said giving it a name might have made an already odd situation “almost too real” — arrived in six parts (legs, arms, torso and head) and the comedian snapped it together within 10 minutes of unboxing. Everything else about the show, though, has seemingly been years in the making.

“It dates as far back as college,” said Winkelman, who will perform a sold-out “Bad Listener” at Up Front at Shadowbox Live on Tuesday, Oct. 29 (a second staging is likely in December). “My senior year of college I studied drama, and the last project you do is a one-person show. And I left school before I could do it, with only a quarter left before graduation, because I was struggling with mental health and struggling with addiction. … This is a way for me to finish that on my own.”

“Bad Listener” started off as a joke, with Winkelman and friends going in circles, each person saying what their one-person show would be. When it got to Winkelman, the comedian cracked that her production would actually be “a one-mannequin show.” Gradually, though, this idea evolved from a silly pun to something more serious, with Winkelman portraying a handful of characters that have extended, one-sided conversations with the mannequin, which Winkelman described as the show's central character, making her a secondary player of sorts in her own one-woman staging.

“There have always been things I wanted to say that I didn't feel would fit my standup voice, and this gave me an opportunity to talk about those things — things that were either more serious or personal,” Winkelman said. “I'm still finding ways to make it funny, but I think there's something humorous about having a mannequin onstage, so that has helped guide me in being able to talk about some of these more serious things.

“I've struggled a lot with mental illness, and it's something I've always wanted to talk about more in my standup, because I think it's a good way to reach other people who struggle with it, but I've always had difficulties with making it funny, maybe because I'm not at a point in my life yet where it's funny to me, which makes it hard to find a way to make it funny to others. So this is a great way for me to talk about it in a personal way, but also sort of deflect from it feeling too personal, because I'm able to talk about it as a character rather than myself.”

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When Winkelman started writing, the material leaned more toward campy humor. But as she continued working, often delivering long monologues at home to the mannequin, which started to take on an increasingly defined, borderline human presence (Winkelman would occasionally catch herself saying “hello” to it before beginning rehearsal), more personal details emerged and the tone of the show began to shift dramatically. The physical presence of the mannequin played a part in this change, with everything down to the positioning of its head shaping the tone of the material.

“Her head is sort of tilted down, which I was initially surprised at, but most mannequins are in stores or window fronts, so they're up higher, and that downward gaze makes sense,” Winkelman said. “But standing next to her, it really looks like she's not paying attention, which started to play into the theme.”

Winkelman portrays a range of characters in the show that orbit the "starring" mannequin. In reality, though, each reflects a different aspect of the comedian's persona, combining to offer as full of an onstage portrait as she has provided up to this point in her career.

“There's a part of myself that's very concerned with safety, and that became a character. Part of me is a mom, so there's a friend of the mannequin that is a mom. Then part of me is a host, which is probably the part most people know of me through comedy, and the first character I play is the host of the show,” Winkelman said.

But even more than offering a chance to better learn what makes her tick, Winkelman hopes that attendees leave with the consideration that each of us, at times, has been that bad listener, and that it's OK to set that phone aside from time to time and engage with one another.

“A running theme throughout is our obsession with screens, and everything being about phones and computers rather than talking to each other directly. … It all becomes so addictive, and we convince ourselves, 'Oh, I need this for work,' or, 'I need this for this or that,' and then we get distracted by all those things that we don't need,” she said. “So, yeah, I've thought about what I want people to leave the show with, and I do want them to leave knowing me better, but I also want them to leave with the encouragement to interact more with the people in their lives.”