One of Canada’s most well-known stars, Jessie Cruickshank, was born in Calgary and has made a name for herself as “the funniest woman on TV.” Learn more about her success story and journey into the entertainment industry on CalgarySki.
Career
Jessie Cruickshank interviewed many celebrities for MTV and eTalk and co-hosted The Hills: The After Show with Levi. This was long before having her three children. Let’s dive into the time that helped Jessie become a beloved TV and media personality.
Born in Calgary, she started her career as the only woman in an improv group alongside Seth Rogen. Soon after, her face became recognizable through her work on MTV Canada.
It didn’t take long for Jessie to gain international recognition as the host of The Hills After Show. The show became incredibly popular, even earning three Grammy nominations. It was broadcast in over 10 countries worldwide, with astonishing ratings in both Canada and the USA.

Why Viewers Love Jessie
Jessie entertained her audience with her openness and sincerity, which made it impossible not to love her. One of her projects, New Mom, Who Dis?, also won the hearts of many. This web series followed the adventures of a woman during maternity leave. What is it like to be a mother of twin boys? Jessie shared stories about pregnancy challenges, talks about sex with kids, and much more.
The show featured a variety of guests, not just Jessie’s friends, but also doctors who shared their professional insights. One of the guests was Justin Trudeau.

“Call Your Friend” Podcast
Jessie keeps the themes of her podcast a secret, but the media can’t stop talking about it. For example, Jessie, a comedian and former TV host, confirmed the first guest in early 2023—one of her sons. It’s worth mentioning that Jessie has twin boys, and in 2022, she became a mother for the third time, giving birth to a lovely daughter. Her husband, TV producer Evan Gatick, is also involved in the podcast discussions. They married in June 2014, and the ceremony took place at Big Daddy’s Antique. That day, they were surrounded by family and friends.
Just two weeks after launching, the podcast became a mega hit, ranking first among the best comedy podcasts on Apple.
Jessie records podcast episodes throughout the week to ensure they are timely. The idea for Call Your Friend was born during maternity leave, driven by her desire to stay connected to the world and keep up with the latest news.
She shared that, with her growing audience, she felt her listeners were at a similar stage. In the episodes, she not only talks about celebrities but also shares her life as a wife and mother.

Jessie Cruickshank: Fun Facts
- Jessie grew up in Vancouver, British Columbia.
- Her school and university years were vibrant and full of activity. She recalls starting her self-discovery with a theater program for special needs in her local high school. Later, she joined the student council. Jessie was always involved in school sports and became a prominent member of Free the Children.
- Jessie continued studying theater in London and later completed a prestigious drama program at the University of Toronto.
- She appeared in the 1996 film For Hope directed by Bob Saget. Jessie started acting as a teenager, with her first appearance for Shoppers Drug Mart.
- Jessie is open about her love for material goods and pop culture. She helps her young audience understand one important thing—happiness is not about what you have but what you can do with it.
- Her career skyrocketed with bold, unrestrained interviews with stars such as Tom Cruise, Chris Brown, Rihanna, Channing Tatum, Bill Gates, and other famous personalities. Another highlight was her “date” with Bradley Cooper, which became an online sensation.

“The Hills After Show?” Best Moments with Dan and Jessie
They became fan favorites, and people still follow their lives today. Interestingly, both Jessie Cruickshank and Dan Levy grew up with famous parents who worked in television. Perhaps this is why they both aspired to be a part of this world.
Jessie was the daughter of the host of Live: Health Picture and took improvisation lessons with Seth Rogen before moving to Toronto. Levy was the son of the well-known Eugene Levy, who worked at Degrassi.
Dan and Jessie also share a common beginning, as they started their careers as VJs on MTV Live. Later, their small series The Hills aired. It was then that the comedians had a chance to showcase themselves, and they succeeded. They went on to host shows like The After Show, The Hills, and The City.
These TV projects taught fans not to idolize celebrities but to poke fun at them. Most would agree, that’s much more fun. Here are some of the most interesting and humorous moments:
- Jessie joined Heidi in a prayer for the success of The Hills.
- Bradley Cooper’s sexual proposal.
- Jessie turned “Heidi” into a funny remix.
Charity Work
Jessie has the ability to always connect with her audience, understand them, and listen. This trait of hers helps her address global issues. She is an ambassador for the charity Free the Children. Jessie even visited India to make a documentary. Critics responded positively to her work, as in MTV Presents: Jessi in India, where viewers see poverty, hunger, and child labor firsthand.
She didn’t stop there; her next project took her to Kenya, where she experienced life with a traditional Maasai family.
Jessie is well-known for her social activism and speaks at conferences with prominent personalities like Jane Goodall, Al Gore, and others.

Sense of Style
While her work on TV, film, and charity could be talked about for hours, Jessie’s sense of style deserves special attention. She has always been called one of the best-dressed TV personalities. She even appeared in many fashion magazines like Elle, Flare, Fashion, and Verve. She tried to launch her own clothing line, and it was a success, as the entire collection sold out in just a few days. Jessie plans to create a new collection.
It’s known that Jessie moved to Los Angeles, where she works on TV projects. She’s also a writer for Hello Giggles! and the host of E! in Canada. She has the energy and passion to be a correspondent for one of Canada’s top entertainment shows, Etalk.
Her unique, candid, and incredibly engaging interview style has made her one of Canada’s most popular TV personalities. It’s nice to see that she doesn’t stop at what she’s achieved and continues working, delighting fans with new projects.