Favorite Vacation Destination: Vancouver (my home town) or Jamaica (just went for the first time and LOVED the beaches, the people, the food, the culture- everything!) 
Favorite Show / Concert / Performer you’ve seen: The Backstreet Boys at The Sphere, Taylor Swift’s ERAs Tour, Pitbull in Las Vegas (I went dressed AS Pitbull… TIME OF MY LIFE)
Favorite way to celebrate yourself: I am a working mom- I don’t really EVER celebrate myself- but for me, going on tour as a comedian is a GIFT to myself. I get to stay in my own hotel room and spend 2 hours on stage with 2000 like-minded women laughing and connecting together in the crowd- there is nothing more challenging… but truly nothing more rewarding.

You literally just wrapped up your Canadian comedy tour. You may be the only person we’ve ever met who has personally been on tour. What’s it like to be on the road? Do you have groupies?

I LOVE being on tour. People will often say ‘how do you do it? travelling, performing, late nights, early flights… that must be so hard’ but for me, being on tour is a VACATION compared to being home with three kids. I get a hotel room… to myself!? I get 2 hours of peace and quiet for Hair and Makeup? I get to GO OUT and laugh every night and meet like-minded women? I have as much fun on stage as people do at my show so… I love it. It’s the most rewarding thing I’ve ever done in my career. 

As for groupies… my fans are THE BEST. They show up with home made ‘Jessi’ merch and signs and gifts for my kids- I feel like I would be friends with all of them, honestly. 

Your show was called the “Now that’s what I call Live” tour, and you positioned it as a call to action for those of us who grew up without cell phones. What do you make of the current 90s / 2000s trends, and how does that nostalgia play into your work?

My comedy tour was 2000’s themed- like DIRTY 2000’s- thousands of women showed up in low rise denim and velour track suits and ugly fedoras and chunky, useless belts- we ALL reminisced on that time in our lives where we’d go out, get drunk, grind with a stranger to Lil Jon with spray tans and belly button rings and digital cameras and flip phones… what.a.time… there was nothing like it.

Now I see Gen Z wearing all of the things we did and posting GRWM videos on TikTok- like no honey… if those low rise jeans don’t get covered in vomit and Smirnoff Ice they don’t count. 

What particulars do you have for your time on tour? Anything you have to eat, avoid, touch, etc. before a show? Any tricks you have to be less nervous in front of the audience?

I am actually very particular- Ironically, I take better care of myself on tour than I do when I’m at home. I’m the opposite of a rock star. I’m on stage for 2+ hours every night so I have to be healthy and strong so I can give 100% on stage- I  started running to get in shape for my tour, I eat super high protein meals, I don’t drink- then I get home and I go back to being my version of Fat Elvis. I let it all go and enjoy my life again. 

You just posted about your kids not only attending your last tour date in Toronto, but actually joining you on stage for it. Do you think they “get” what you do now, and how do they feel about it? What questions did they have for you after the show?

I travel so much for work, I was on the road for 4 months with this tour so I really wanted my kids to see me in action and understand what I do… I’m still not sure they get it. LOL. If they do, they are not impressed. They came out on stage with me to 2500 screaming fans and still told me to wipe their bums the next morning, you know? But that is the beauty of being a parent- it puts everything into perspective. 

A lot of us were introduced to you through New Mom, Who Dis?—your extremely popular Facebook Watch series. Do you see yourself returning to this interview-style episodic content in the future? 

I would LOVE TO- stand up is a very solitary thing- I write on my own, I stand on stage by myself- I miss engaging with other people and I honestly think it’s what I do best.

My podcast Phone A Friend with Jessi Cruickshank is my outlet now for funny conversations with interesting people. It is a pop culture podcast for (elder) Millennials- when there is something in the culture that I don’t understand, I get to Phone A Friend- it can be a celebrity: I’ve phoned Lindsey Lohan, N’Sync, Dan Levy- but I’ve also phoned a ‘Labubu Collector’ a tween, a Paparazzi, an Only Fans Model… anyone who can answer my (usually dumb) questions about what (the f) is going on in Pop Culture at any given moment.  

Who are a few other comedians you admire or whose careers you follow? (We typically ask about women entrepreneurs, so feel free to answer from that perspective if you’d prefer.)

I lead with fearlessness. For me, that is the secret to my success, whether I’m dropping it to Pitbull on stage or interviewing Prime Minister Justin Trudeau … I do things and ask questions without any fear. So I look to other women who have done the same. I have been called ‘Canada’s Chelsea Handler’ and that was the BIGGEST compliment- I think she’s always been such a trailblazer as a woman with a voice in comedy. I love Ali Wong- I first watched her when I had newborn twins at home and she made me realize how powerful my voice could be as a mom and a comedian.