The stand-up comedy and TV series is launching its first special on Veeps

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Near the end of Jessie Cruickshank's first comedy film, Minivan Money, the Calgary native calls herself “Toronto's saddest bra.”

It's a testament to his considerable skill at improvisation, but also a testament to how deeply he understands his fans. As usual, the women in the audience are asked to take off their “sad bras” and take them on stage. Cruickshank judges these artifacts based on their incorporeality and awards the winner a crown. Sounds funny, right? Not everyone thought so. When he first created the beat for his stand-up routine, both his tour manager and the Live Nation team were adamantly against the idea. In fact, they assured him it was a mistake and would never work.

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“They” don't, no, no…you can't do that. Nobody's going to throw their vests at you,” Cruikshank tells Postmedia in a Zoom interview from his home in Los Angeles. I said, “I know my audience.” They said, “Trust us, we know the audience that goes to the shows. We know comedy viewers… “I felt confident and had to fight. Even when we were shooting the special, the team was like, 'You're not going to have bras. I don't think anyone throws their bras at the camera.' »

In fact, Cruikshank had 48 “sad” vests thrown at him in the opera house while taping the special. Over the course of the tour, Cruickshank estimates that more than 500 people have been thrown on stages across Canada. He may officially be a relative newcomer to the world of stand-up comedy, but he knows his fans. Some of them have been following him for nearly 20 years, starting with his MTV personality as co-host of The Hills: The After Show with pre-Shitt's Creek Dan Levy.

“I understand so much who the people who come to see me are that I can create a show that resonates with them,” he says. “Bras are a really good example.”

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In fact, it's a major part of his comedy. Unflattering bras, overpriced minivans, pre-school daddy cravings, creepy babies and other indignities of modern motherhood and family life are all part of Cruikshank's first comedy special, which airs May 30 on Veeps. It also delves into 2000s nostalgia and looks back at early celebrity crushes. He appreciates all the aging Backstreet Boys, for example, and refuses to acknowledge Leonardo DiCaprio's transformation from bad boy to 49-year-old bearded man with his father's body. It's very funny, but also very relatable to the women in the audience who have gone through similar experiences. The special begins with Cruikshank's three children – his six-year-old twin sons and his two-and-a-half-year-old daughter – narrating in a pre-recorded introduction before the comedian walks out wearing breast pumps. In a way, it's like a visual joke. On the other hand, it is not. Cruikshank's daughter was just six months old when she embarked on her first stand-up tour in 2022. So it's not actually an act, she's pumping breast milk on stage.

“My tour manager and I were trying to figure out how to breastfeed before and after the show, because I'd be doing meet and greets after the show, rehearsals,” she says. “I actually had to drive very seriously on the road and we were FedExing milk to my six-month-old baby. At a certain point I just said – excuse my language – “(heels) this! I just go on stage.' Most of my audience had young babies, or might one day. They will understand. Instead of doing a quick pump in the dressing room, putting on a mask, and going on stage, I thought why not show what's going on behind the scenes, which is that I'm actively pumping breast milk for the baby while I'm doing it.”

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In 2022, Cruikshank crossed Canada twice with his two-and-a-half-hour show, Up Close and Too Personal. It was originally slated for 2020 before COVID intervened. Born in Calgary and raised in Vancouver, his first stab at comedy came in high school when he was part of an improv team that included future stars Seth Rogen and Nathan Fielder. But his career arc was extraordinary. Traditionally, comedians start out with a stand-up in hopes of landing TV gigs. Cruickshank rose to prominence interviewing celebrities on eTalk before hosting MTV and CBC's Smartest Person in Canada. But his stadium gigs, notably the 2015 Canadian Country Music Awards and the four-and-a-half-hour Junos galas three years in a row, have convinced him that he's not just ready for stand-up, he's ready. already doing it. He wrote his own jokes and monologues for the Junos and the CCMAs, and reckoned, “If I could write jokes about Shawn Mendes or Brett Kissel — unknown Canadian artists — for four hours and destroy it in a stadium, I could do it for myself. »

“Being a woman in this business, I was always considered a guest, even though the man next to me was called a joker and I was called a driver,” she says. “I was in a situation where I was writing my own material and co-hosting a show with two or three male writers. Every time I scratch my head and think, “I'm smiling the same and doing the same job, but for some reason – because I'm a woman, I've never been put in that category.”

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In the fall, Cruickshank will embark on another stand-up tour in Calgary, beginning with a return performance at the Bella Concert Hall in September. Cruickshank has a high-profile platform for testing new material. In February 2023, he launched the podcast Friend's Phone with Jesse Cruickshank, with an episode featuring Dan Levy. It quickly topped the charts as both Apple's top comedy podcast and podcast in general. In addition, she finds ample opportunities to develop and test material in everyday life as a busy mother.

“A lot of up-and-coming comedians are going on stage at night clubs and testing their material,” she says. “I test my material on pre-school moms. If I think something is funny, I want to try the joke at a moms' meeting. If it gets a big laugh, I know I have something and work with it from there. If he dies, I'll move on if there's no reaction on the birthday of the kid I'm going to. That's really how I handle it.”

Minivan Money will launch on Veeps on May 30th.

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