Mayor thrilled to be publicly and hilariously mocked by comedy royalty

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This article was published 21/07/2025 (430 days ago), so information in it may no longer be current.

The questions were absurd, random and insulting. But that’s how clueless, comically corpulent and cringe-inducing television celebrity interviewer Jiminy Glick rolls.

And for Winnipeg’s mayor, who bore the unrelenting brunt of the bloated, fictitious character’s improvised comedy chaos at Assiniboine Park Saturday evening, it was an over-too-soon dream come true.

“I’ve never been a part of anything like what I experienced Saturday night,” Scott Gillingham said Monday, still basking in the glow of the exquisite pain he endured sitting on stage opposite one of Canadian comic actor Martin Short’s beloved over-the-top characters.

“(It was) really a cool thing for a Canadian who’s been a fan of Martin Short’s for decades.”

The 75-year-old Short was one of the headliners at the weekend’s Great Outdoors Comedy Festival.

Gillingham’s appearance as Glick’s victim came as a surprise for the audience, as did former mayor Brian Bowman’s star turn during Short’s 2015 performance at the Club Regent Event Centre.

“You were adopted,” Glick asked/told Gillingham in his obnoxious, declarative and high-pitched voice.

The mayor responded that he, in fact, had not been adopted.

“Oh, sorry, I hate for you to find out this way,” came the reply.

The conversation also at one point entered a “lightning round.” The questions included, “If you grew another nipple anywhere in your body, where would you put it?” and “Are we putting breath mints in the wrong end?”

The mayor answered with “in the middle” and “next question,” respectively.

“As the one being interviewed by Jiminy Glick, you don’t really say a lot. It just kind of comes at you like a firehose. You laugh and you cringe and you try to have some sort of witty response, but it’s over in a heartbeat. But it’s a lot of fun,” said Gillingham, adding he was laughing too hard to answer some of the questions.

It was a nice change from his day job, he said.

“What I like about, obviously, about that experience, but the comedy festival as well, is that there’s so much that is heavy and serious in our lives and in our community, in our world right now. Being able to come together as a community and laugh is kind of refreshing,” he said.

The Great Outdoors Comedy Festival, which also features John Mulaney, Whitney Cummings, Jeremy Piven and the Trailer Park Boys, among others, is visiting multiple Canadian cities (along with Spokane, Wash.).

“To see Winnipeg as being central to the vision of the nationwide festival brings a spotlight to Winnipeg. That’s really good,” Gillingham said. “Obviously, it brings economic spinoffs to the community, as well. Whether it’s people coming in from out of town to watch the shows and hotel nights, restaurants. It just brings a buzz to the city.”

Gillingham said he’s hopeful organizers will expand the local portion of the event in the future.

“They absolutely see a future here in Winnipeg and (a) goal to continue to grow the comedy festival here in our city,” he said.

joyanne.pursaga@freepress.mb.ca

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