Local jokester rides comedic convergence from pizza purveyor to artistic director of the Winnipeg Comedy Festival

Winnipeg Free Press

25-04-2025

Did you hear the one about the pizza cook who went on to become the artistic director of the most watched comedy festival on Canadian television?
In the spring of 1990, a then-19-year-old Dean Jenkinson was working part-time at Sbarro, an Italian-flavoured spot in the CF Polo Park food court.
Jenkinson, a dry wit blessed with a deadpan delivery, was cracking his co-workers up so much over the course of their shifts together that they ultimately convinced him to enter an open-mic competition at an Osborne Village comedy club.
RUTH BONNEVILLE / FREE PRESS
Comedian Dean Jenkinson is celebrating his fifth anniversary as artistic director of the Winnipeg Comedy Festival, which kicks off next week.
He enjoyed the experience immensely — more about that in a sec — and 35 years and thousands of punchlines later, Jenkinson is presently toasting his fifth anniversary at the helm of the Winnipeg Comedy Festival, which runs in venues across the city from April 29 to May 4.
(The joke was on him; during his inaugural year as artistic director in 2020, the annual weeklong event was forced to shift from its usual springtime slot to late summer as a result of COVID-19. Ditto in 2021.)
Although Jenkinson isn't scheduled to perform at the 2025 festival — highlights will air on CBC Television later in the year — he refers to his director's role as being the best of both worlds.
'With all the sacrifices you have to make as a standup in this country — around travel and being away from home and kids and family — I'm really grateful to have something stable in the industry that's comedy-related, and that I get so much satisfaction out of,' he says, seated in an Academy Road coffee shop where he is sporting a This Hour Has 22 Minutes windbreaker, a memento of the decade-and-a-half he spent writing for the award-winning TV program.
'That said, every time I do get the chance to step on stage, I'm reminded of why I fell in love with comedy in the first place… how much fun it can be when you and the audience are locked in, when they believe in you and you believe in yourself and every word coming out of your mouth is gold. Now, whether that's actually the case or not is another story altogether.'
Jenkinson, 54, was born in Edmonton, the second of three brothers. His family moved to St. Norbert when he was four, after his father accepted a teaching position at the University of Manitoba.
Describing himself as a pretty decent student who regularly pulled straight As, he quotes one of his favourite actors when asked if, as one might expect, he ever fit the bill of class clown.
'Billy Crystal once said there's a difference between being the class clown and being the class comedian. The class clown is the guy who runs naked across the football field, while the class comedian is the guy who convinces him to do it. I was probably more the second guy.'
Jenkinson wasn't sure what direction he wanted to go in after graduating from Silver Heights Collegiate in 1989.
He was gifted on the electronic organ, which led to a gig playing at Winnipeg Jets home games at the old Winnipeg Arena, but he doubted there was much of a future in that.
'Billy Crystal once said there's a difference between being the class clown and being the class comedian. The class clown is the guy who runs naked across the football field, while the class comedian is the guy who convinces him to do it. I was probably more the second guy.'
It was assumed he would attend university because of his grades and he eventually chose architecture as his field of interest, believing it would be a good blend of creative and analytical thinking.
'What I quickly learned, however, is that I didn't have any particular talent or passion for it, and I started getting the first Cs of my life,' he states.
He stuck with the three-year program nonetheless, and it was shortly after his first year of studies when he landed the aforementioned job at the food court.
That led directly to the open-mic experiment, an overwhelming success thanks to a set of circumstances Jenkinson vows he wouldn't repeat in a 'million years.' To boost his confidence, he invited practically everyone he knew to come cheer him on.
'There were tables of people from work, tables of people from school, tables of friends and family. They laughed at everything I said and if that hadn't been the case, who knows if I'd have tried again,' he says, mentioning if he remembers correctly, his monologue that evening revolved mainly around recent movies.
'Honestly, it probably wasn't until my fourth or fifth time on stage when I ate it pretty hard and was like, 'oh, I guess you don't kill every night.''
Around the same time as his comedic debut, Jenkinson landed a second part-time job, one that involved delivering singing telegrams for a party and event-planning business called Scheme a Dream.
Among the office staff was Jon Ljungberg, an experienced comedian and the future host of Citytv's Breakfast Television. After Jenkinson informed Ljungberg that he, too, was interested in standup, Ljungberg let him know that Rumor's Comedy Club on Corydon Avenue was in the market for local hosts to warm up audiences for headliners.
Scot McTaggart, who managed Rumor's for six years before opening the Academy Road restaurant Fusion Grill in 1996, picks up the story from there. McTaggart had been in his position for three months in June 1990 when, within the space of a few hours, he lost both of his regular emcees.
He adopted a next-person up mentality by handling the host duties himself, but it soon became abundantly clear that live comedy wasn't his forte.
MIKE DEAL / FREE PRESS FILES
Comedian Dean Jenkinson in 2006.
A few minutes into his second night as host, a person seated near the front of the Rumor's stage made the sound effect of a bomb whistle — loud enough for everyone in the room to hear — along with the ensuing explosion, as McTaggart's attempts at humour failed over and over again.
'I had already seen Dean's act, I think at the Comedy Oasis, when he contacted me through Jon and I hired him immediately, owing to the fact that my short experience running a comedy club obviously meant I was a great judge of talent,' McTaggart says, breaking into a grin.
'Or maybe it had something to do with me having zero interest of ever getting on a stage again, and Dean being more than willing to do just that.'
McTaggart says one of the challenges of hosting as many as seven shows a week was that there were a fair number of Rumor's regulars who frowned upon hearing the same routine twice in a short period.
That never bothered headliners who simply moved on to the next city, but it presented a problem for locals such as Jenkinson to constantly come up with fresh material.
'Dean, or 'Clean Dean' as we called him, because his stuff was always clever, bright and for the most part, G-rated, was always up to the task,' McTaggart recalls.
'I don't want to say he was a normal guy because there's nothing normal about wanting to get up in front of a group of people with your pants by your ankles, but honestly he was. He loved comedy and he loved the science of putting a joke together. I never heard a bad word about Dean, which is almost impossible to say in that biz.'
By the late 1990s, Jenkinson's shtick had caught the attention of the producers of CBC Winnipeg's suppertime news hour. They were looking for somebody to deliver weekly satirical rants about whatever was in the headlines and they invited Jenkinson to their Portage Avenue studio to audition.
'I guess they liked what I had to offer because I ended up doing that for a few years,' says Jenkinson, who would often accompany himself on guitar, Adam Sandler-like, as he cracked wise about crime statistics or goings-on in the mayor's office.
His work there opened the door to take on writing opportunities for The Royal Canadian Air Farce, The Debaters and, in 2011, for Kunal Nayyar and Simon Helberg — more commonly known as Raj and Howard from the hugely popular CBS sit-com The Big Bang Theory — when the pair hosted a Just for Laughs skit called Tribute to Nerds, at a showcase event in Montreal.
JOE BRYKSA / FREE PRESS FILES
Dean Jenkinson as Mr. Chuckles on stage at the Winnipeg Comedy Festical in February, 2007.
'It was definitely a challenge writing jokes and skits for other people,' Jenkinson.
'Initially there was a lot of self-doubt and asking myself, 'is this good enough? Do I dare show it to them?' I gradually got over that hump until it became a case of 'Oh, you didn't like that joke? Well here's another, and another…''
Comedian Lara Rae co-founded the Winnipeg Comedy Festival in 2002, and served as artistic director until Jenkinson succeeded her five years ago. Rae can't think of a person better suited to the role than Jenkinson, with whom she's worked on numerous occasions.
'We first met in 2001 when I helped him get a job for a sit-com on Global called Big Sound, then shortly after that we did a fringe play together, a musical called How Do You Know When You're Done?' Rae says, when reached at home.
'We have a very good and strong friendship and he was one of a handful of male friends who was there for me when I transitioned in 2015, which could have been a tricky thing.'
Rae says Jenkinson has the perfect mix of business acumen and comedic know-how that's required of an artistic director.
'Standups are a unique breed. We're outliers, we're iconoclasts, we're trouble-makers… and within the confines of television, which involves a lot of money and decision making, we don't always flourish,' says Rae, who chose Jenkinson to be her best man.
'One of the things I'm especially proud of with Dean is his ability to grow and develop in the 'business' part of show business. That's where he's really matured these last two decades because when it came to the 'show' part, he was always pretty solid.'
Jenkinson, the father of a 14-year-old daughter, 12-year-old son and 15-year-old stepdaughter, says it's funny, but he can't remember ever entering into a conversation with his parents along the lines of what his backup plan was if 'this comedy thing' failed to pan out.
'I look back and think God bless them,' he says polishing off the last of his coffee.
RUTH BONNEVILLE / FREE PRESS
It's been 35 years since Dean Jenkinson entered an open-mic competition at a local comedy club.
'I mean, were they quietly shitting bricks, thinking they had this smart child who might grow up to be a doctor or lawyer, who's now working for minimum wage and chicken wings. Maybe they had intentions of intervening at some point, but luckily my income grew at a commensurate rate with my responsibilities and expenses, and it all worked out.'
The same way Jenkinson used to solicit tips from veteran comics at Rumor's and other clubs he played, young up-and-comers now seek him out for advice.
He tells them a large part of it is being in the right place at the right time, and being a person who doesn't drop the ball when an opportunity presents itself.
'It's like any other job, really. Be respectful, show up on time, don't make waves… A lot of it is just being a professional.'
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