FROM TABOO TO TRENDY: Way Cool Tattoo Artist Bert Jackson

When Bert Jackson opened the doors of Way Cool Tattoos 24 years ago in Oakville, his parents were dead set against it. Back then, tattoos belonged to the realm of misfits and rebels, not to their private-school-educated son. 

Fast forward to today and tattoos, once a symbol of rebellion against the mainstream, have become, well, mainstream. 

“I’ve become a respectable member of the community!” Bert says, sounding almost surprised. “You’d be amazed how many parents come in here giving consent for their 16- or 17-year-old kids.” Some have even gone under the needle themselves. “We had a mother and daughter get matching flowers. It was something really meaningful to them and it was really sweet to see.”

Bert credits reality TV shows like Ink Masters and Miami Ink for changing people’s perceptions of body art. Suddenly, tattoo parlours weren’t intimidating dens of ink and needles for those on the fringe but places of creative self-expression for people from all walks of life. “People who didn’t know much about tattoos were seeing heart-warming stories of people getting tattoos, like someone wanting to commemorate their deceased grandfather. And they’re thinking ‘what a nice way to celebrate them. And oh, I lost somebody in my life, maybe I’ll get a tattoo.’”

Perhaps the real MVP is social media. Every selfie became an opportunity for celebrities to flaunt their fresh ink as a statement of style, and was more likely to attract Instagram likes these days than raised eyebrows. 

“If Rihanna has a new tattoo, then all the girls will come in and get it. It’s the same thing for basketball players,” he says. A wide cross-section of clients visits his studio. They include young and returning customers, but also nurses, firefighters, police officers and teachers alike seeking out his expertise. He’s skilled in many disciplines, including traditional Japanese art and realistic animal designs. 

“Things have really changed since I got my first tattoo in my early 20s.” And so has his life. He grew up in Toronto and was “very much an urban kind of dude” when he got a Buddhist motif inked on his chest, representing the root causes of human suffering. Since then, he’s had a family and moved to Oakville, which promised a healthier lifestyle and more nature. Oh, and that first tattoo? It now sits among an ever-expanding ink collection adorning his body. 

Becoming a tattoo master was a natural fit since he was, and still is, a visual artist. His home is covered with vibrant-coloured paintings and eclectic sculptures he made for shows held in Toronto galleries. One notable piece, a bronze sculpture of a hammerhead shark, commemorates the death of Rob Stewart, the Canadian activist and director of films like Sharkwater. Another, an aluminum-cast sculpture of Donald Trump’s head on the body of a menacing octopus, serves as Bert’s social commentary on the former president. “I made three of them pairing Trump’s head with an animal I thought said something about him as a person. There’s one at the tattoo shop,” he says, taking a pause and smirking before he continues. “It’s a pig.”

At Way Cool Tattoos, Bert encourages his team of five tattooists to display their artwork as well, and fosters a friendly, creative atmosphere that’s more akin to a hair salon than the stereotypical surly tattoo parlours of the nineties. “We try to be disarming,” he explains, emphasizing the collaborative nature of the tattooing process with clients. “I love the creativity involved and that I’m able to express myself. But you know, what I really like about tattooing is the social aspect,” Bert adds. “People come to me with ideas that I never would have thought of. Not only do you have a lot of interesting projects, but you also meet a lot of interesting people.”

The studio has been located in the Kerr Village for so long – it’s the oldest tattoo shop in Oakville – that he’s known as “the tattoo guy.” Even his parents, albeit still opposed to tattoos, have accepted his line of work. “I guess they’re like, ‘if you can’t beat ‘em, join ‘em.’” 


Way Cool Tattoos
494 Kerr Street, Oakville

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