Silver anniversary, comedy gold

This year, Dean Jenkinson celebrates six years as the Winnipeg Comedy Festival’s artistic director and the festival’s 25th anniversary.

The Winnipeg standup is also a contributing writer for This Hour Has 22 Minutes (a role he’s had since 2007), and can brag, if he wants to, that he’s crafted material for such acts as the Muppets, Joan Rivers, Neil Patrick Harris and Sarah Silverman.

During his time on the comedy scene, he has grown somewhat philosophical and, as the festival announces its full lineup for the April 20-26 event, he reflects on subjects such as regionalism in Canadian standup and hot-button topics like “woke” versus edgy humour.

Packing Winnipeg venues with laughing locals while helping regional comics springboard toward a broader national and international audience is what the festival is all about, he says.

“When comics start out, they often write very local material. As they mature, they realize they need to write more universal jokes. Even if you’re telling a local story, you want to explain it in a way a broader audience can understand,” says Jenkinson.

The lineup features some of Winnipeg’s best comics — including Mike Green, Danielle Kayahara and Lara Rae — and Canadian comedy circuit favourites such as Big Daddy Tazz and Yumi Nagashima. (The Free Press’s own Mike McIntyre will appear on the Laughing With the Stars showcase of amateur local celebs.)

Then there are Canadian big guns, such as Shaun Majumder and singer-songwriter Jann Arden.

“Jann Arden is one of our pillars this year,” says Jenkinson of the famously funny singer-songwriter and actor.

“She’s not a comic but we’ve been chasing her for a number of years. We’re thrilled to have her hosting one of our TV mega shows.”

The mega shows are the festival’s big tapings at the Burton Cummings Theatre, which also feature hosts Brooke Lynn Hytes (RuPaul’s Drag Race), Juno Award-winner Dave Merheje (Just For Laughs) and Chris Wilson (This Hour Has 22 Minutes).

The festival’s gala is its marquee event, where the wiry and fiery Majumder, one of the country’s best-known comics to have made most of his career in Canada, takes centre stage.

“Shaun’s been around since the early days of the festival and he’s always been a Winnipeg favourite,” Jenkinson says of the former This Hour Has 22 Minutes star.

There are also smaller, club-style shows at the Gas Station Arts Centre and CBC’s popular The Debaters on April 25 and 26, where comedians argue playfully about absurd and humorous topics in front of a live audience.

“The first tapings were the proof that this could actually be a thing that happened in Winnipeg, and now that’s gone on for 20 years,” Jenkinson says.

He reflects on the role that public funders and broadcasters play in spotlighting — and setting the terms for what flies in — Canadian comedy at festivals like Winnipeg’s.

“It’s important to (CBC) that what we put on the air is stuff that they feel like they can do in good conscience and defend against,” he says.

“(Each event in Canada) has their own style and taste, and if you’re outside that, you’re kind of left to your own devices, which is unfortunate. There are lots of Canadian comics who make a living touring and doing clubs, staying true to their own style.”

This shifts to a conversation about “anti-wokeness,” a recent movement toward a more politically incorrect style of humour that reacts against progressives’ perceived ideological straightjacketing of the comedy industry.

While some critics of “wokeness” insist that they’re merely restoring comedy for comedy’s sake, this movement has also inspired many voices to simply shift in the opposite direction ideologically, using the pretence of comedy to push not-so-ironic right-wing takes.

“My guiding light for myself, and my advice to other comedians, is to know what your intent is with a joke, and to consider whether you’re punching up or punching down,” says Jenkinson.

“I do believe that there are jokes that are cruel and do actual harm to communities.”

It’s true that some of Canada’s greatest comedic forces — people such as Norm MacDonald and Russell Peters — have done away with our country’s expected politeness and said things that make people blush.

“Somewhat contradictory things can be true all at once,” says Jenkinson, who has programmed a family-friendly show, two queer comedy nights and Bannock Bums, a showcase of Indigenous comedians, at this year’s fest. “One year, something I put in my letter to (visiting comics) was a reminder that their jokes are both tools and weapons. And what they choose to build, and what they choose to destroy, is entirely up to them. And that what they do is powerful and makes a difference.”

As the festival approaches its 25th anniversary this year, Jenkinson strikes another tone — proud, even a little nostalgic.

“You can probably count on one hand, or maybe just a little bit more onto the second hand, the number of avenues there are in this country to get in front of a national audience,” he says.

In this respect, the Winnipeg Comedy Festival is in rare company.

And, most importantly, the festival is a lot of fun for Winnipeggers.

“(Audiences) have a blast. Being in a room full of strangers anonymously in the dark, sharing laughter, is one of those magical things that is so hard to describe,” says Jenkinson.

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