The Toronto Shoemaker Making the Impossible for Hollywood

From a workshop in Parkdale, Jeff Churchill and Jitterbug Boy have made footwear for Marvel, DC, Fast & Furious and some of the biggest productions in film. But Churchill never intended to become a shoemaker — and after more than two decades building his business, he nearly walked away from it altogether.

There is an unlikely connection between some of Hollywood’s biggest films and a workshop on a side street in Toronto’s Parkdale neighbourhood.

Inside, shelves and walls are crowded with shoe lasts, tools, leather, half-finished footwear and the accumulated machinery of a trade that, at first glance, appears deeply traditional.

Jeff Churchill is not.

For close to 30 years, Churchill has been making shoes. His company, Jitterbug Boy, has produced custom footwear for film and television projects including Marvel films, Guardians of the Galaxy, Thor, DC productions, Superman, Fast & Furious and Wicked. The company has become sufficiently established that Churchill says costume departments across the English-speaking film industry know the Jitterbug Boy name. Jitterbug Boy Final YT Transcri…

The strange thing is that none of this was the plan.

“I’ve been making shoes for close to 30 years,” he says, “[and] had never had any intention of becoming a shoemaker.” Jitterbug Boy Final YT Transcri…

In fact, Churchill’s route to becoming one of Toronto’s most unusual craftspeople began somewhere else entirely.

From theatre to shoemaking

Churchill started working in theatre when he was around 14. He did almost everything: carpentry, costumes, props, driving trucks and operating follow spots.

The ambition was to become a set and costume designer.

Eventually, he did.

Then he discovered he didn’t particularly want to be one.

“So I spent so many years working towards this goal, got to the goal and realized, no, this isn’t for me,” he recalls. Jitterbug Boy Final YT Transcri…

Shoemaking emerged from that world rather than through the traditional route of studying the craft. Jitterbug Boy initially worked across circus and theatre, including London's West End.

Then a recession hit theatre budgets.

Churchill travelled to London hoping to reconnect with the theatre industry as it began to recover. Instead, he repeatedly heard that although theatre was returning, budgets for custom footwear weren't.

By chance, he met people working in film.

That changed everything.

Churchill estimates that over two weeks he had around 24 meetings with people in the film industry. Production in London was booming, but there was a problem: there wasn't enough specialist infrastructure to support it.

“They didn’t have a shoemaker,” he says.

Jitterbug Boy had found its opening.

Film work quickly went from being one part of the business to almost all of it. The company doubled both its workforce and physical space virtually overnight. Within roughly two years, film and television had taken over the shop. Jitterbug Boy Final YT Transcri…

When success starts to feel like a machine

There is a version of this story that could end there.

An unconventional Toronto maker discovers a niche, Hollywood comes calling, the company grows and everyone lives happily ever after.

The reality was messier.

At its largest before the pandemic, Jitterbug Boy had a crew of 21. Churchill found himself responsible not only for making things, but for constantly balancing people, projects and deadlines.

During Wicked, he says, 16 people were working in the shop and Jitterbug Boy produced somewhere around 120 to 130 pairs of shoes for the film.

Churchill was barely making any of them himself.

He would draft something, hand it to somebody else and immediately move on to the next job.

Then the next.

Then the next.

“It just started to feel a bit too much like a machine,” he says. Jitterbug Boy Final YT Transcri…

For somebody who had spent his life making things, success had gradually pulled him away from the thing he actually enjoyed.

After 18 years, he was exhausted.

Churchill had already spent years trying to restructure the company so he could become more hands-on again. Eventually he decided that incremental changes weren't working.

He gave his employees and regular clients nine months’ notice.

Jitterbug Boy was going to wind down.

“I’m tired, I’m burnt out, and I just want to be a maker again.” Jitterbug Boy Final YT Transcri…

The plan that disappeared

Churchill wasn't planning to abandon the film industry.

Instead, he wanted to change his relationship with it.

Rather than running a large independent workshop serving multiple productions, he planned to work directly within individual film productions — something other departments routinely do, but shoemakers generally don't.

Almost immediately, it appeared to be working.

A designer offered him a position on a major production. Then the show fell through.

Shortly afterwards another designer approached him about a huge project in New Zealand. Churchill spent months closing and scaling down his Toronto operation in preparation for the move.

Then came the dual Hollywood strikes.

The film industry ground to a halt.

The New Zealand production was delayed by a couple of months. Then another couple. Eventually, after millions had already been invested in the project, it was cancelled.

Churchill had spent months dismantling the business he had built and was suddenly left without the job that was supposed to replace it.

He was also carrying substantial debt. Jitterbug Boy Final YT Transcri…

By the beginning of 2025, he made another decision.

“Nope. I’m recommitting myself.”

He hired a crew and started again.

“If there’s one thing that I’ve learned in this industry,” Churchill says, “you got to bend or else you’re just going to snap.”

The rebuilt Jitterbug Boy is deliberately smaller. Churchill can be choosier about projects and has managed to reclaim more of a life outside the workshop.

He bent.

A shoemaker who never went to shoemaking school

There is another unusual part of Churchill’s story.

He is self-taught.

“I’ve never gone to school. I’ve never taken a course.”

Nearly three decades into his career, Churchill jokes that his knowledge of the formal anatomy of a shoe is “still shit” because he never learned from textbooks. Jitterbug Boy Final YT Transcri…

Instead, his approach comes from theatre — and particularly the mentality of props departments.

You're presented with a problem. You have a deadline. You have whatever materials happen to be available.

Now make it work.

“And that’s how I work,” he says. Jitterbug Boy Final YT Transcri…

It has produced a culture at Jitterbug Boy that is almost defiantly nontraditional.

Churchill says traditional shoemakers haven't always fitted easily into the workshop because they arrive knowing how a shoe is supposed to be made.

His response is essentially: that may be how it's traditionally done, but that's not necessarily how they do it here.

Instead, he prefers talented craftspeople who can learn Jitterbug Boy's particular methods.

That willingness to ignore convention becomes useful when a film production arrives with an absurd request and an equally absurd deadline.

Jitterbug Boy routinely turns shoes around in three days.

They have done it in 36 hours.

It “should be impossible,” Churchill says.

“But we figured out a way.” Jitterbug Boy Final YT Transcri…

Making impossible shoes comfortable

The challenge isn't simply making something look extraordinary.

Someone has to wear it.

Actors may spend long days standing, walking, running or performing in footwear designed primarily to look as though it belongs to another century, another planet or a superhero.

Churchill therefore works backwards from something decidedly less glamorous: the running shoe.

“What I’ll always try and do in film is to make things feel as much like a running shoe as possible, in whatever form they are,” he explains.

That can mean constructing elaborate science-fiction footwear or period boots around running-shoe lasts.

The audience sees the character.

The actor, ideally, feels a trainer.

That matters because, as Churchill puts it, “You’re only as good as your last job.”

When an actor puts on a pair during a fitting and says they're comfortable, Churchill knows he's succeeded. The actor is happy. The designer is happy. And in an industry built around temporary productions and constantly changing teams, that experience helps lead to the next call. Jitterbug Boy Final YT Transcri…

Why Toronto still matters

When Churchill originally decided to close Jitterbug Boy, he assumed he would leave.

Rebuilding the company had an unexpected consequence.

It made him want to stay.

Churchill says he now feels a stronger connection to Toronto and particularly Parkdale. If the New Zealand opportunity appeared again today, he isn't convinced he would take it.

“I’d probably say no because I really like my life now.”

He can walk to work. Bring his dog. See his wife for dinner.

After decades spent building a company whose work travels to film sets around the world, those ordinary things have acquired their own value.

And there is something else keeping him here.

Jitterbug Boy has created something in Toronto that wasn't here before.

Churchill's route into shoemaking was accidental. His methods are unconventional. His business almost disappeared. The industry it relies upon was turned upside down.

Yet in a Parkdale workshop, a small group of craftspeople continue solving strange problems for some of the world's biggest productions.

“We’ve been able to kind of carve out this niche that wouldn’t exist here,” Churchill says.

“You wouldn’t be here talking to another shoemaker in Parkdale right now.”

“It’s just who we are.” Jitterbug Boy Final YT Transcri…