Teaching old comic new tricks is easier with a strict deadline

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This article was published 07/04/2015 (4119 days ago), so information in it may no longer be current.

The problem was specific. The solution was obvious. And as a result, the Winnipeg Comedy Festival is both a collaborator in and a beneficiary of John Wing’s latest comedy conundrum.

“It was a very practical decision: I needed to write a new hour (of material), and I knew I wouldn’t do it unless I had a deadline hanging over my head,” says Wing, who is debuting his new deadline-pressure-cooked comedy in the form of a sold-out one-man show, Old Enough to Know Better, on Wednesday at 8 p.m. at the Gas Station Arts Centre.

“So I called (artistic director) Al Rae and asked if I could do a one-man show, knowing that that would be enough of a deadline to get me working on it. It’s a simple as that.”

As for the rationale for creating this large volume of new material, Wing says it was just time to turn over the content of his comedy act.

“I’m at that 10-year point again,” he explains. “I’m 55 now, and I believe that every 10 years, the material you have starts to lose its relevance — it’s not that it’s stale; it’s simply that it’s no longer you.

“The bulk of my (recent) material was written around the time when I was 45 to 48; it’s been changed and improved and there has been new stuff added, but the majority of it was stuff I started writing when I was 45. That’s 10 years ago, and I’m a different person now, and the audience is starting to catch on to the fact that there’s a level of contrivance and a lack of honesty in the material. It’s not me anymore, so I have to write a new set.”

“I mean, I’m not Louis C.K.; I can’t do it every year. But I knew I had to do it, and I knew Winnipeg — and the Gas Station (theatre) — was the place to bring it. It’s a great audience, I could probably sell it out, and it would be a great place to debut a new hour.”

The show’s title — Old Enough to Know Better — is self-explanatory; Wing says the topics addressed in the new 50s-focused material include self-perception in middle age (how old you are, as opposed to how old you feel), how language has changed in the digital age (LOL!), and how each succeeding generation both brags and complains about what it didn’t have growing up (for Wing’s parents, it was television; for the comedian, it was the Internet).

“There are a lot of jokes about unintended benefits and unintended consequences,” he explains. “I just started working with three or four topics — things I like talking about, and things I need to talk about — and built from there.”

Wing, a product of Sarnia, Ont., who has called Los Angeles home for more than two decades, is the only performer to have appeared at all 14 editions of the Winnipeg Comedy Festival. His wry observations on life, parenting and relationships have made him an in-demand commodity in many different corners of the entertainment world, from comedy clubs and theatres to television (he was a semifinalist on America’s Got Talent) and cruise ships (he spends several months per year entertaining on Royal Caribbean, Norwegian and Carnival Cruise Lines ships).

In addition to his one-man show and a set in Thursday’s rest-and-relaxation-themed gala, Wing will also contribute an argument to Sunday’s taping of CBC’s The Debaters, will receive a career-achievement award at the inaugural Mic Awards ceremony and will be the subject of the festival’s first celebrity roast on Sunday night.

“I’d hoped that they would pick some interesting people to roast me, but alas,” he says, getting an early shot in at roastmaster Tyler Morrison and panellists Rebecca Kohler, Al Rae, Bruce Clark, Simon Rakoff and Darcy Michael. “Actually, it sounds like fun. I’ve written a few jokes in case I have to make a bit of a speech at the end. I’ve never been roasted before, but it sounds like fun.

“I’ve also never received a lifetime achievement award; I guess that’s a sign of something… It’s very nice of them to give me an award, just like it’s very nice for them to keep having me back. I know the year will come when they won’t ask me back, and I’ll have to be absolutely OK with that because they’ve been so nice to me for all these years.”

brad.oswald@freepress.mb.ca Twitter: @BradOswald