If you’re an elder millennial you know her well.
She’s been a fixture on your tv since the early-2000s when she burst on the scene to help contextualize what Heidi, Spencer and LC were up to. From hosting, to finding her voice on stage and online, she has found success thanks in part to her incredible gift for comedy.
Her career has taken her all over the world and through it all she has never forgotten the special place Canada holds in her heart.
I’m Craig Baird and this is Canadian History Ehx … Biography…
Today, I share the story of a prominent Canadian who was part of an improv group with Seth Rogen and Nathan Fielder in high school and that helped her discover her love for entertaining.
This is…Jessi Cruickshank!
Jessi’s and my story begin in the same location…Calgary.
She entered the world two years after me on July 17, 1982.
Jessi moved to Vancouver when she was five years old and called BC home until University where she attended the University of Toronto…. but I’m getting ahead of myself.
Because her inspiration for her future began much earlier. thanks to her mother, Joyce Resin.
She was the host of Alive! The Picture of Health, Canada’s first network television health and wellness show which aired on CBC.
It was seen in 30 countries around the world.
Joyce followed that with the first network television program for people over 50, The Best Years, later called 50UP!
Growing up in Vancouver in the 1990s, Jessi witnessed the entertainment industry all around her.
The success of The Beachcombers in the 1970s and 1980s, showed that British Columbia’s Lower Mainland could be a true Hollywood North.
Before long, other television shows and movies were using Vancouver as a backdrop.
And it had an impact.
From her elementary school being used as a film set for a month, to seeing David Duchovny regularly, it was all par for the course of Jessi’s early life.
Along with early brushes with celebrity, Jessi learned entertainment was always a career option.
This is also when she learned that she had a gift for comedy by making her own family laugh.
When she reached high school, Jessi joined an all-male improv group at Point Grey Secondary High School.
If the name of the school sounds familiar… it’s because the film Superbad was based on the experiences of the film’s writers Seth Rogen and Evan Goldberg when they attended Point Grey.
The duo’s production company, Point Grey Pictures is named after it.
Seth first achieved success with the role of Ken Miller in Judd Apatow’s critically-acclaimed show Freaks and Geeks.
His appearance on the show helped forge a friendship with Apatow who was impressed with his ability to improvise on set.
But for everyone in high school who knew Seth as the guy with bleach blonde dreadlocks, it was hard for them to believe that he was on an actual network television show.
Jessi had also caught the acting bug while still in school.
Her first role was in the1996 film For Hope.
(PAUSE MUSIC TRANSITION MAYBE MIDROLL)
Directed by Bob Saget, the stand-up comedian, actor, best known for portraying Danny Tanner on the sitcom Full House, the film was about a young woman suffering from scleroderma.
It is an autoimmune disease that at the time was unrecognized.
The story is loosely based on events that directly affected Bob Saget and his family, and mainly his sister, Gay Saget, whom he lost to scleroderma, two years earlier, in 1994.
He made the film as a statement of the frustration his family had been left with after his sister had been misdiagnosed and mistreated for the symptoms, so it was a deeply personal project for him.
The film premiered on November 17, 1996, on ABC and for the first time Jessi was on screen in the role of Beth.
After high school, Jessi went to the University of Toronto where she studied Drama and English.
By the time she graduated she very quickly realized that compared to the United States, there were not as many opportunities in Canada, so she set her sights on becoming a MuchMusic VJ.
Which at the time was a great entry point into the world of entertainment having launched the careers of George Stroumboulopoulos, Master T, Sook-Yin Lee, and Rick Campanelli before her.
MuchMusic, now just called Much, launched on Aug. 31, 1984, as essentially a Canadian version of MTV.
It helped showcase Canadian talent who would otherwise find a tough time getting exposure south of the border.
Every few weeks while she was in college, Jessi sent letters to MuchMusic asking for a job, saying she would even intern for free.
Although she didn’t get an internship, she did manage to find her way to a music channel.
That means working with little to no budget… which forces Canadians like Jessi to do everything themselves.
It basically working in entertainment means it’s l baptism by fire.
As a host on MTV Live, Jessi figured out how to watch the beta tapes, make edit notes and cut the tape with the editor.
It was a lot of work, but it taught her how to write, produce and do everything pretty much by herself.
Jessi got into the industry at the same time as social media was in its infancy.
Facebook had been around since her college years and Twitter was just becoming a thing but very quickly it became a place where one could directly connect with an audience.
It provided Jessi insight into who was watching and helped her realize there wasn’t much difference between talking to friends and talking to the audience through the cameras.
That shaped her conversational style and helped her connect with audiences, even when she wasn’t sure they were watching. She also had to be her own stylist.
Jessi took her first paycheque and bought a $400 tank top.
It was an extravagance she had never done before, nor since, but for her it was a big deal to be able to spend that kind of money on herself.
Of course, the plan was to wear it on air and then return it the next day.
But things didn’t exactly go to plan.
Jessi may have been surprised to know that people were watching her on MTV Live, but everything was about to change thanks to a bunch of kids from Laguna Beach.
(PAUSE MUSIC TRANSITION POSSIBLE MIDROLL).
Laguna Beach: The Real Orange County was a reality television series which premiered on MTV on September 28, 2004.
It focused on the personal lives of Lauren Conrad, Lo Bosworth, Stephen Colletti, Kristin Cavallari and Talan Torriero.
It was a massive hit for MTV and by 2005, Lauren Conrad, the show’s star, had moved to Los Angeles.
That’s when the network ordered a spin-off series and The Hills was born as a way to chronicle the lives of Conrad, her housemate Heidi Montag, her neighbor Audrina Patridge and her colleague Whitney Port.
The show was another massive hit as two to five million viewers tuned in each week.
And in Hollywood North Jessi was about to ride that wave to a whole new level of fame thanks to a loop hole in TV licensing.
At the time, MuchMusic was the only Canadian channel to have a music license. MTV Canada programing only had a talk licence, which meant programming couldn’t include music videos… it would be a blessing in disguise.
MTV Canada launched The Hills: The After Show as a way to contextualize the network’s flagship series in order to fit the channel’s mandate.
It essentially became a place to discuss the program immediately after with input from studio audience members, callers, emailers, and webcam participants.
It would feature Jessi and her new co-host, Dan Levy.
Meant to fill time, no one was expecting it to become a major hit.
The first season didn’t have a set, and Jessie and Dan Levy sat on the floor, drinking real martinis, with half their guests having a bit too much because it was filmed live on Friday nights at 10:30 p.m.
It quickly became a phenomenon.
As ratings grew week to week, the decision was made that for the season finale, the doors would open to a live audience.
Both Jessi and Dan worried no one would show up.
They spent the morning texting friends asking them to come.
That night, 100 chairs were set up and everyone held their breath.
When doors opened, the first people to walk in were Toronto Police asking what was going on.
That’s when Jessie and Dan Levy looked outside for the first time.
At street level at 888 Yonge Street, at the doors of the historic Masonic Temple there was a crowd waiting to get in.
The Hills After Show was a bonafide hit and MTV US took notice… and bought the show.
It became the first-ever live simulcast television show made in Canada to air in the United States
And that’s how Jessi’s little show made Canadian broadcasting history.
The success came at a price.
What was okay in Canada, didn’t always fly in the United States.
New rules dictated the content of the show which made Jessi longed for the previous freedom they had to experiment.
By the time The Hills and the After Show came to an end in 2010, Jessi’s career was going strong, and Levy went on to become the co-creator and star of the critically-acclaimed Schitt’s Creek.
Jessi moved to Los Angeles and by 2012 she was co-hosting the CW series, Oh Sit! — a high-octane musical chairs competition alongside comedian Jamie Kennedy.
That New Year she appeared on First Night 2013 with Jamie Kennedy.
It was broadcast live on December 31, 2012, from outside Grauman’s Chinese Theatre in Hollywood and it quickly became infamous.
The special has MANY technical problems (including microphone gaffes and communication issues), featured scenes described as being “surreal”, the very New Year being counted in too late and spontaneously ended with an impromptu fight breaking out on stage over the credits.
Jessi was the sole bright spot as she interviewed guests throughout the show, such as Drake Bell and Olympic gold medalist Dawn Harper.
(BEAT)In 2014, Jessi returned North of the 49 to host Canada’s Smartest Person.
CBC producers sorted through thousands of would-be geniuses to find the first 32 contestants to cerebrally battle it out for the title over eight episodes.
She hosted the program for three seasons as she was also travelling across Canada giving motivational speeches for Free the Children Events having hosted, We Day Alberta in 2012.
With her star rising, she began hosting major events including the Canadian Country Music Awards and the Junos which she emceed for four years in a row.
That helped her make the realization that she was really more than a host, quote,
“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.”
For the Junos had written her own jokes and monologues, so it.
didn’t take much for her to write her own shows.
She told the Calgary Herald,
“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.”
In 2015, toured campuses in Canada with her one woman show called Behind-the-Scenes where she gave film screenings and gossip sessions.
Quote
“I get to travel to colleges across the country and screen a free movie. On top of the free movie, it’s a totally intimate one-on-one session with me where I have promised to divulge all of my secrets about people, things that I have witnessed in Hollywood, who’s low maintenance, who’s high-maintenance.”
]Just a few years later in 2016, Jessi became a co-host of the daytime talk show, The Goods.
She hosted segments on style and design.
Shifting to a daytime show also meant that the rules she liked to break in late night television couldn’t be broken.
The audience was older and there were standards that had to be maintained which didn’t fit with Jessi’s edgy sense of humour, and it took her time to adjust.
Sadly, CBC announced that the series would be cancelled after two seasons and the final episode aired on May 10, 2018.
The Goods however was nominated for a Canadian Screen Award for Best Lifestyle Program or Series at the 6th Canadian Screen Awards.
By then Jessi had pivoted again and her drive for innovation led to CBC literally giving her a camera and telling her to make what she wanted.
And Jessi was going digital.
Her online presence was fully cemented.
Which was a good thing because her personal life had changed.
In 2014, she married Evan Gatica.
The two met when Jessi was auditioning for MTV.
She had been determined to put together a tape, and her dad had a friend with a production company in New York. When she landed at the office she expected to find some slick old man, instead she found a young, tall, handsome film editor named Evan.
He took her to a cool little restaurant in the Lower East Side where Cameron Diaz and Justin Timberlake were quietly eating in the corner.
The rest as they say is history and halfway through her time at The Goods Jessi found out she was pregnant.
Jessi expected to have the baby then get back to work but then she found out she was pregnant with twins and in her words, her life flashed before her eyes.
As much as the Goods had been a safe place for her… it was still hard to be a working mom of infants.
As a new mother, Jessi she wanted to show others online what motherhood was really like
That reaction inspired Jessi to share more of her own experiences, shaped by her unique sense of humour.
And she gave birth to a digital show called New Mom Who Dis.
Jessi said in an interview,
“After I had my twins, I thought I would never work in entertainment again. I could barely shower, let alone make a TV show. One day, I was rushing out the door to meet with a big production company in L.A. about creating a new comedy series – my babies were screaming, I was pumping breast milk while trying to draw on my eyebrows and I thought – ‘This is funny.’ So, I pitched them a comedy series about my new life as a mom.”
The show became the number one Canadian Series on Facebook Watch.
As social media became more a part of all our lives Jessi’s online reach grew as well.
Whether it is through her podcasts, video content or her stand-up tours, she has taken control of her own career to immense success.
In 2022, Jessi crossed Canada twice with her two-and-a-half hour show Up Close and Too Personal.
She originally planned to do the show for 2020, but the COVID 19 pandemic derailed that.
This year, she is on her second comedy tour called Now That’s What I Call Live Tour.
Jessi called it a gift to her millennial brethren who grew up watching her.
She has called touring the greatest joy of her career because it allows her to connect to the people who grew up watching her, in person. It also gives her an appreciation for where she is in her own career.
Even with all her success, Jessi has never forgotten the place that made her.
Recently, she was offered a stand-up special in the United States. The producers wanted her to film in Los Angeles, but she refused, and they shot it in Canada instead.
Part of that was national pride. The other part was that for Jessi, no one produces better TV than Canada.
Jessi is doing what she has always loved to do…
Make comedy.
And she gets to do it in a way she never thought possible decades ago watching David Duchovny walk his dog.
I would like to thank Jessi Cruickshank for sharing his time with me. In two weeks, we will be back with another episode of Canadian History Ehx Biography.
I will be talking to musician Ron Sexsmith.
