Growing up in Willowdale, when he wasn’t delivering newspapers on Hollywood Avenue, Gerry Dee focused most of his energy on sports: from playing tennis at Bayview Village Tennis Club to excelling on many teams during his high school years at De La Salle College in Rosedale.
Dee even went on to study kinesiology at York University. Later, after receiving his teaching degree from St. Francis Xavier University in Nova Scotia, he would return to De La Salle to teach phys. ed. and coach hockey.
It comes as no surprise, then, that Dee would be able to segue his career from stand-up comedian to humorous reporter on The Score.
In 2007, after placing third overall in season five of Last Comic Standing, the sports network came knocking.
“They wanted to try something different,” says Dee, noting Charles Barkley as the funniest athlete interviewed on his recurring segment Gerry Dee: Sports Reporter.
“We’re going to get back into it when things settle down,” he adds.
Right now, Dee’s schedule is pretty busy. Every year he plays more than 150 sold-out stand-up shows across Canada and internationally. His Life After Teaching 2012 tour has him performing across Canada from October until the end of the year.
And then there are the summers spent in Halifax taping the CBC comedy Mr. D, in which Dee plays the lead.
The television show, in which he stars as underqualified high school teacher Gerry Duncan, is based on his previous comedic performances referencing his 10-year career in education. Picked up for a second season, new episodes start airing in January.
“Every stand-up in the country has aspirations to have a sitcom,” he admits.
If you’re wondering which of his former teachers Dee looks to when developing his character’s substandard habits in the classroom, he’s quick to admit he has few memories of the bad ones.
“You tend to focus on the good ones,” he says. “I was very fortunate.”
Mr. D pays homage to quite a few of Dee’s positive experiences growing up. His character teaches at Xavier Academy, in honour of Dee’s alma mater. And Principal Callaghan was inspired by his former coach at De La Salle.
“Not the character,” he explains, “but that’s how I got the name.”
With over 800,000 weekly viewers, the show’s been a runaway hit, joining together other local stars like Jonathan Torrens and Wes Williams (otherwise known as Maestro Fresh Wes). The entire cast is scheduled to perform a live show on New Year’s Eve at Toronto Centre for the Arts.
The biggest difference for Dee between being a stand-up comedian and an actor?
“Stand-up is doing your own thing, by yourself,” he says. “But at the end of day, you still have to be funny.”
And being funny is something that has come naturally to Willowdale’s prodigal performer.
“Once I started getting some laughs and making a little bit of money and could feel a positive response, I kept pursuing it,” he recalls.
Kicking off on the local Yuk Yuk’s stage — just like many comedians before him, such as Norm Macdonald — Dee first performed there in the early ’90s. Mark Breslin, the comedy club’s Torontonian creator and a fellow York University alumnus, remembers a young Gerry Dee as “a white Bill Cosby.”
“He was very smooth,” Breslin says. “He was clean, squeaky clean — in a way that a lot of the comics aren’t. That gave him a very different vibe.”
Breslin goes on to say, “Besides being funny, because there’s a lot of funny people out there, Gerry has a very respectful tone toward the audience, and that’s rare.”
Dee’s career cannonballed from there. In 2002 he was the first Canadian in 27 years to win the San Francisco International Comedy Competition, a platform that launched the careers of such notable comedians as Robin Williams, Dana Carvey and Ellen DeGeneres. He also won the Canadian Comedy Award for Best Male Stand-Up in 2008.
Dee’s been at it full-time ever since, attracting legions of loyal fans and accolades both in Canada and internationally.
His latest foray is a book that takes a hilarious behind-the-scenes look at life inside the classroom: Teaching: It’s Harder Than It Looks hit bookshelves Oct. 23.
“A lot of people think teaching is a walk in the park. Yeah, yeah. You have no idea! You think teachers just stand up there and lecture on and on — and get paid for it. Here’s the truth: there are only two good reasons to become a teacher. The first is July; the second is August,” he writes.
This hilarious tell-all shares the trials and tribulations of Dee’s teaching days, including exams, smart kids, the cafeteria, school dances, the staff room, cheating, teen romance and parent meetings.
“This is my tribute to school life,” reads the book jacket, “from the point of view of a teacher who, like many other teachers out there, occasionally taught hungover (and lied about it), sometimes lost his students’ exams (and lied about it) and enjoyed staging impromptu baseball games in the middle of history class just to kill some time.”
Dee speaks of what every teacher has been thinking: the job isn’t always easy. (He admits that “a lot of teachers go home every night complaining about preparing lessons. I went home every night to learn the lesson.”)
But although they may be one spontaneous ball game away from a nervous breakdown, teachers continue to make a difference in the lives of boys and girls everywhere … even if the road to success gets a little bumpy along the way.
For Dee, his secret of survival in front of the chalkboard is his modus operandi on the stand-up stage: “I learned how to put on a performance,” he says.
And the two acts are not dissimilar: performing for applause from a late-night Yuk Yuk’s audience takes prowess similar to holding the attention of teenagers who would rather be anywhere but at their desks.
“There’s not a teacher out there who hasn’t bent the rules a little in order to win that much-sought-after prize: respect in the classroom,” Dee admits in his signature candid way.
With a comedy career stretching from the stage to the screen, Dee has not only earned that respect — he’s getting straight A’s across the board.
