Taking the Stage
Jennifer Stewart, Theatre Orangeville’s new artistic director, steps into the spotlight.
On the first day of rehearsals for Theatre Orangeville’s Young Company production, Hadestown: Teen Edition, which hit the stage in late July, the theatre’s newly appointed artistic director, Jennifer Stewart, smiles widely as the group of 12- to 18-year-olds harmonizes around a soloist. As all the singers realize they finally hit the right note, music director Aaron Eyre exclaims, “That’s hot!”
In this early outing, technically the first production of her tenure, Stewart appears content to let others – the kids and the music director – fill the space. She is clearly pleased with the sounds echoing through the theatre company’s Dream Factory rehearsal site on the Fergus Road just outside Orangeville.
“This cast is extraordinarily talented,” says Stewart. “You see some kids get excited when they finally hit that high note or sing all the syllables in the right order. It’s like alchemy!”

Stewart’s stint as artistic director began in January, when retiring artistic director David Nairn, who had been at the helm of the professional theatre for 26 years, stayed on for a time to help smooth the transition. Stewart’s first season is this fall.
She moved to Orangeville with partner, Daniel, and son, Luka, in January. They had previously divided their time between Stratford, Ontario, and Málaga, Spain. In fact, Stewart’s last gig before taking on her new role was in a pantomime in Málaga. A well-rounded theatre artist, she also recently toured Ontario, performing her one-woman show, Confessions of Motherhood, which she wrote, produced and performed.
Now in Orangeville, she says she’s committed to making theatre for this community. “David’s been taking me around to meet everyone, which has been great because it’s a really great way to be integrated into the community super-fast. Now I know where to get my car fixed, get my dry cleaning, get my coffee. I’ve met all the owners, which is special. I feel privileged.”
A season of change
Nairn, a larger-than-life creative force who is moving on to the next phase of his career, announced his departure in June last year. The organization cast a wide net to find its next artistic director, one who fit the mandate to create Canadian shows and who is committed to its values of integrity, excellence and kindness for the community. When Stewart applied, she appeared to fit like a glove.
An element of the interview process called on her to pitch a season. “There was a magic number,” she recalls. The undisclosed number related to the number of artists the theatre can afford to hire over the course of a year. “And my season just hit the number, right on. David was asking me yesterday, ‘You didn’t know the number?!’”
Says Sharyn Ayliffe, Theatre Orangeville’s executive director: “Jennifer just brought such magnetic energy and seemed to have a firm understanding of life in a community like ours. There’s a ton of similarities between the rural culture of Stratford and Orangeville. There was no apprehension on her part – she was just all in and it felt right.”

In what now looks like classic foreshadowing, Nairn and Stewart first crossed paths on stage years ago, during their acting days. In 1992, the pair appeared together in a production of Camelot, the musical about King Arthur, in Grand Bend.
“David played King Arthur … and I played Tom, the boy at the end of the play,” says Stewart, as she sits with Ayliffe in the Theatre Orangeville offices at Highway 10 and Broadway. “So, King Arthur comes up to me and says, ‘Run, boy, run. Tell my story … that once there was a place called Camelot.’
“So I just thought it was kind of fitting that now I’m taking over David’s legacy at Theatre Orangeville. Thirty-three years later, it’s a great story. You couldn’t write that.”
“Kismet,” Ayliffe adds.
Made for theatre
Stewart is steeped in stage culture. She grew up in theatre hub Stratford, Ontario, where her Grade 2 teacher, Lois Burdett, taught her students Shakespeare: “She would take the story and translate it into a choral speaking!” Burdett tasked the young Stewart with playing Viola in Shakespeare’s Twelfth Night and mentored her in Shakespeare’s art.
Burdett had connections with the Stratford Festival and, that season, gave her class the opportunity to mount their production on the theatre’s main stage for the festival’s acting company. The next year, the festival’s artistic director at the time invited Stewart and other students to be in a professional production of The Winter’s Tale.
Stewart’s mother initially hesitated to accept the offer – her daughter was only eight years old and had never acted professionally. “She didn’t want me hanging out with actors!” Stewart recalls with a laugh. But Burdett, whose work introducing children to Shakespeare was recognized in 1996 when Governor General Roméo LeBlanc awarded her a Meritorious Service Medal, assured her parents that their daughter would be well taken care of. As Stewart talks about the experience, her ability to tell a great story sparks excitement in the room. “I loved it. It was so magical.”


From that beginning, Stewart’s acting experience at Stratford expanded, as she performed in more Shakespearean productions and theatrical classics ranging from The Pirates of Penzance to Fiddler on the Roof. She went on to earn a master of fine arts in theatre directing at the East 15 Acting School, which is affiliated with the University of Essex in England. During this time, she had the opportunity to travel to places such as Moscow and Bali to study theatre directing.
Today Stewart takes in as many productions as she can, anywhere in the world. These may include opera, Shakespeare, a Toronto mainstage musical or an artsy fringe show in the basement of a bar. “You need to see a lot of shows, different actors, see what’s going on.”
On a recent layover in London, England, before hopping on a flight to Spain, her husband’s home country and a place the family often visits, Stewart took a few hours off to see Clueless the Musical in the city’s West End.
The show was a blast, but she also had ulterior motives. “I was kind of checking it out for the Young Company for the future,” she says, mulling over her own review of the musical. “It was very dance-heavy. Although it doesn’t have to be. They just had a dance-y ensemble, but you could have varying degrees of choreography for the students.”
Theatre Orangeville’s bright future
One notable difference between Nairn’s tenure and Stewart’s is that the artistic director and executive director will now share responsibility for running the theatre, reflecting a growing trend among professional theatres in Canada. Previously, the artistic director was the top dog, but Nairn recommended the theatre’s board of directors adopt the change. Finding a new artistic director who would be familiar with Theatre Orangeville was unlikely, which meant Ayliffe’s role as a supportive and Orangeville-experienced executive director became essential.
Having worked with the theatre since 2011, Ayliffe has seen it weather a variety of storms, most significantly the Covid pandemic, which began 11 days after she was promoted to the role of general manager in 2020. A challenge for sure, but Ayliffe says the theatre has emerged stronger, just as it has with Stewart’s arrival: “Theatre Orangeville seems to find these kismet moments.”
Post-pandemic, Theatre Orangeville has seen a great deal of growth. Its budget is double what it was when Ayliffe originally joined and she says, “There’s been a growth in how much youth programming we’re doing, and while the mandate has stayed the same, I think the interpretation of that has evolved as the community has evolved. There’s been a lot of evolution in bringing more diverse voices to the stage.”
As Stewart and Ayliffe prepare to launch Theatre Orangeville’s 32nd season this September, they’re looking forward to what they’ve taken to calling a “season of wonder.”
“Well, our first mainstage play is called The Wonder of It All,” Stewart says with excitement. She will direct this world premiere of playwright Mark Weatherley’s comedic examination of the trials and tribulations of a 25-year marriage.
The other world premiere is the pantomime Rapunzel: A Braid New World, by Debbie Collins and Nairn, who will direct the production. Common Ground, a romantic comedy by John Spurway, is next on the bill, followed by Murder at Ackerton Manor, Steven Gallagher’s farcical murder mystery that spoofs the works of Agatha Christie, and The Wedding Party by a Stewart favourite, Kristen Thomson.
One of the staples of a Theatre Orangeville season is often a work by Norm Foster, arguably Canada’s most popular playwright. He has been a friend of the company since collaborating with Nairn in the early 2000s and is a favourite of avid Theatre Orangeville-goers. The Norm Effect, a three-day festival of staged readings of some of his best-loved works, begins September 17. Joining Foster on stage for the readings will be Nairn and other Theatre Orangeville actors and friends.
Most notably, all the plays in the season are Canadian. “That’s our mandate,” Stewart explains, “and has been for a very long time. Which we’re very proud of right now, in this moment, in history. Not many theatres can say that.”
Back in the Dream Factory rehearsal space, the Young Company actors have finished rehearsing the first song in their musical production. There are dozens of songs to go, but the wonder these young people absorb along the way will make the challenge worth it.
And as Day 1 of rehearsals comes to a close, a world of kismet moments and memories to be made is waiting for Stewart in the wings.
More Info
Rapid Fire — Getting to Know Jennifer Stewart
What better way to get to know Theatre Orangeville’s new artistic director than to pepper her with questions? Here goes.
First time you saw a play or musical, and your age
Pirates of Penzance at the Stratford Festival! I was seven years old.
Last play you saw and rated 5/5
Sense and Sensibility at Stratford. Loved it. Five out of five.
Most unusual play you have seen
In England you can see a play a night. They have little theatres in pubs. There was a musical called Money, very unusual, but kudos to them for doing it. But we left at intermission and had a drink!
Greatest lengths to squeeze in a viewing
Flying to London on a layover on the way to Spain and catching a matinee of Clueless the Musical.
Most remote location where you have seen a play
Bali. Moscow, too. Because we were students and got to see everything for free!
Book ahead or rush seats
Depends. I like to read reviews because if it gets good reviews, it might sell out fast.
A Broadway production that intrigues you
There’s a play in New York City right now called John Proctor Is the Villain – a new play in a high school setting with students studying The Crucible, debating whether John Proctor really was the villain. I would love to see it.
How an actor can ace an audition with you
Good question. Be prepared. Know your stuff. Do your monologue from a Canadian play!
Favourite Shakespeare play and why. And favourite Shakespeare character and why
I love The Two Gentlemen of Verona and Julia, the lead, and her journey in that.
Favourite musical
Gypsy. Antonio Banderas put the show on in Spanish in Málaga and he modernized it. I saw it three times.
Favourite one-hander
Well, there is a show called Age Is a Feeling by Haley McGee. It is a choose-your-own-adventure play about life, and she has 12 stories and the audience chooses six of the stories through the course of the evening. You only see six stories, so she must edit the play as she is going along to tell the six stories. You want to see the play again because you want to hear the other stories.
Favourite ensemble performance
Hadestown. Everyone is on stage the whole time and doing a little bit of everything.
Contemporary playwright whose works you like
That’s interesting because I am in my Canadian playwright era right now. Kristen Thomson I really enjoy. She wrote The Wedding Party. And Haley McGee too. She wrote The Ex-Boyfriend Yard Sale. It is a one-person show where she takes items from ex-boyfriends and asks, “Can I sell this to make money to pay my Visa bill? And what did that relationship cost me? And is selling that item worth the cost of the relationship?”
Best director you’ve worked with recently
In the last couple of years, I have been directing more than acting. But I know that one of my favourite directors was Jack O’Brien. He directed Hairspray in Toronto. He would come and whisper in your ear a few words that could crack open everything in an instant, get you thinking in a different way. Because talking too much confuses actors. It’s not thinking, it’s doing. He taught me a lot as an actor that I try to incorporate in my directing.
An opening-night ritual
I love the check-in circle, getting everyone on the same page, grounded, ready to do the show.
Best seat in the house at the Theatre Orangeville Opera House
None yet. To be determined.
Pet peeve in the theatre
Cell phones on during the show.
Best director advice
Trust your instincts. Both in theatre and in life.
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