Nick Hart answers a question during the first mayoral debate of the 2019 election at the Barrymore Theatre.

Nick Hart says that performing standup always demands vulnerability.

“Especially with jokes, you’re giving away a piece of yourself to the audience in exchange for a laugh,” said Hart, the wry Madison comic and recent mayoral candidate.

But for the comedy special that he’ll be filming on Friday night, Hart will make himself vulnerable in new ways. Yes, there will be a set of all-new material at the show. But Hart will also be telling emotional stories about friendship, death and the supernatural — plus, he’ll be breaking out a guitar for a song or two.

“I wouldn’t call myself the musician,” Hart said. “But I can strum the guitar a little bit. I can strum four chords.”

He added: “It’s definitely out of my comfort zone. I’m not a fan of singing in front of people ... It could be a really cool thing, or an absolutely beautiful disaster. We will see.”

The live comedy special “Is This Void Even On?” takes place at The Winnebago on Friday night, with performances scheduled for 7 p.m. and 9 p.m.

Hart has become one of Madison's best-known standup comics over the past decade. In 2018, he performed on “Conan,” regaling a studio audience with a voyage of discovery he’d had at the grocery store. (“I just found out green onions and scallions are the same thing … and for those of you who didn’t laugh at that, now you know.”) In 2017, voters named him Madison’s funniest comic, and that same year he took third in the Seattle International Comedy Competition.

Madison residents not plugged into the comedy scene may also recognize him from his two mayoral campaigns, one in 2011 and another earlier this year.

Friday night’s comedy special came together after M.O.D. Media Productions, a local multimedia and design firm, approached Hart to discuss a potential collaboration. The firm boasts a mission of supporting local institutions and artists that it feels deserve exposure.

“M.O.D. has supported local artists since its inception and continues to through productions such as this,” the firm noted in a press release for the show.

Hart had long been interesting in recording something beyond just a comedy special, but what he described as a “show” — something involving more than just a set of jokes.

The result is a performance featuring 45 minutes of comedy, before a pivot to 45 minutes of storytelling and songs.

Hart said the stories and music will mostly be about Dana, a friend of his who passed away two years ago from cancer. He said he’ll share stories about meeting Dana, about what she was like, learning about her diagnosis and prognosis, and being out of town during her death, and how that affected his grieving process.

Hart said that the performance is partly a way for him to heal. He also said it’s a fulfillment of a promise he made to Dana the last time he saw her, at a benefit for the Comedy Club on State two weeks before she died.

“I told her, ‘I love you. I promise I’ll love you for the rest of my life. I’ll tell stories about you. I’ll sing songs about you. Just know that you’ll be remembered,’” he said.

Hart said that the night will ultimately be an exercise in opposites: He’ll start the night by “building a wall” of jokes, before making a hard pivot and “knocking it down” with the second half.

Also an exercise in opposites, Hart said, is the musical component. He said he’s not a big fan of comedians who whip out guitars to “play silly songs,” so he decided to go in a different direction with his music.

“It’s doing the exact opposite of what a comedian with a guitar usually does. Instead of silly songs, there will be songs about life,” he said.

The shows on Friday night will be at 7 p.m. and 9 p.m. The cover is $10.

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Erik Lorenzsonn is the Capital Times' tech and culture reporter. He joined the team in 2016, after having served as an online editor for Wisconsin Public Radio and having written for publications like The Progressive Magazine and The Poughkeepsie Journal.