Part of the crowd: Calgary-born comedian Jessi Cruickshank knows her audience, because they are just like her

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Near the end of Jessi Cruickshank’s first comedy special, Minivan Money, the Calgary native does a bit called “the saddest bra in Toronto.”

It is a showcase for her considerable skills at improv, but also a testament to how deeply she understands her fans. The routine requires women in the audience to take off their “sad bras” and pitch them onto the stage. Cruickshank judges these artifacts on their inherent unsexiness and crowns a winner. Sound funny, right? Well, not everyone thought so. When she was first developing this bit for her standup routine, both her tour manager and the team at Live Nation were strongly opposed to the idea. In fact, they assured her it was a mistake and would never work.

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“They said ‘no, no, no … you can’t do that. No one is going to throw their bra at you,’ ” says Cruickshank, in a Zoom interview with Postmedia from her home in Los Angeles. “I said ‘I know my audience.’ They said ‘Trust us, we know audiences who go to shows. We know comedy audiences … ‘ I felt so confident and I had to fight. Even when we were shooting the special, the team said ‘You’re not going to get bras. I don’t think anyone is going to throw their bras on camera.’ ”

In fact, Cruickshank got 48 “sad” bras thrown at her at the Opera House while taping the special. During the tour, Cruickshank reckons more than 500 were eagerly thrown on stages across Canada. She may officially be a relative newbie to the world of standup comedy, but she knows her fans. Some of them have been following her for nearly 20 years, dating back to her early days as an MTV personality co-hosting The Hills: The After Show with a pre-Schitt’s Creek Dan Levy.

“I have such a sense of who the people who come to see me are that I’m better able to create a show that resonates with them,” she says. “The bras are a really good example of that.”

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In fact, it’s central to her comedy. Sad bras, over-priced minivans, lusting after pre-school dads, scary toddlers and other indignities of modern motherhood and family life are all part of Cruickshank’s first comedy special, which starts streaming May 30 on Veeps. She also delves into nostalgia for the 2000s, pining for some early celebrity crushes. She rates all of the aging Backstreet Boys, for instance, and refuses to accept that Leonardo DiCaprio has morphed from bad-boy hunk into a bearded 49-year-old with a dad bod. It is very funny,  but also meant to be witheringly relatable to women in the audience who have presumably gone through similar experiences. The special starts with Cruickshank’s three children – six-year-old identical twin boys and her two-and-a-half-year-old daughter – hamming it up in a pre-taped introduction before the comedian walks out wearing breast pumps. On one hand, it’s a bit of a visual joke. On the other hand, it isn’t. Cruickshank’s daughter was only six months old when she embarked on her first standup tour in 2022. So it’s not really an act, she does pump breast milk on stage.

“My tour manager and I were trying to figure out how I could pump breast milk before and after the show, because I would have a meet-and-greet after the show, rehearsals,” she says. “I actually had to pump on the road pretty seriously and we were FedExing the milk back to my six-month-old. At a certain point, I just said – pardon my language – ‘(expletive) this! I’ll just pump on stage.’ Most of my audience have had small babies or might have them one day. They are going to understand. Instead of just quickly pumping in the dressing room and putting on some facade and walking out on stage, I thought why not show what is going on behind the scenes, which is that I am actively pumping breast milk for a baby while doing this.”

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In 2022, Cruickshank crossed Canada twice with her two-and-a-half-hour show Up Close and Too Personal. It had originally been planned for 2020 before COVID intervened. Born in Calgary and raised in Vancouver, her first stab at comedy was in high school when she was part of an improv team that also included future stars Seth Rogen and Nathan Fielder. But her career arc has been unusual. Traditionally, comedians start with standup with hopes of landing TV gigs. Cruickshank gained fame on MTV and by interviewing celebrities on eTalk before hosting CBC’s Canada’s Smartest Person. But it was her live hosting gigs in stadiums – specifically The Canadian Country Music Awards in 2015 and the four-and-a-half-hour Junos gala three years in a row – that convinced her she was not only ready for standup but had actually already been doing it. She wrote her own jokes and monologues for the Junos and the CCMAs and figured “If I can write jokes about Shawn Mendes for four hours or Brett Kissel – obscure Canadian artists – and crush it in a stadium, surely I can do it for myself.”

“Being a woman in this business, I was always considered a host even if the man standing next to me doing the same job was always called a comedian and I was called a host,” she says. “I found myself in circumstances co-hosting a show where I would be writing my own material and the men would have two or three writers. I would scratch my head every time and be like ‘I’m getting the same laughs and doing the same job, but for whatever reason – because I’m a woman – I was never put in that category.”

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In the fall, Cruickshank will be going on another standup tour which will begin in Calgary in September with a return performance at the Bella Concert Hall. Cruickshank has a high-profile platform to test new material. In February 2023, she launched her podcast Phone a Friend with Jessi Cruickshank with an episode featuring Dan Levy. It quickly topped the charts as both Apple’s top comedy podcast and overall podcast. Other than that, she finds ample opportunities in her day-to-day life as a busy mother to develop and test material.

“A lot of standup comedians who are starting out are going up on stage at night at the clubs, trying out their material,” she says “I try out my material on the pre-school moms. If I think something is sort of funny, I’ll like casually try the joke out at a mom gathering. If it gets a big laugh, then I know I have something and I’ll work on it from there. If it dies, if it doesn’t get any reaction at some child’s birthday party that I’m at, then I move on. That’s really how I work it out.”

Minivan Money launches May 30 on Veeps.

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