After just a few minutes spent in the presence of proud Port Hoper Paul Bailey, it’s evident that the 78-year-old has many stories to share. Fortunately for us, many of those stories of Port Hope and his life within it are shared through his bold and eye-grabbing paintings.
Bailey spends every morning after breakfast until lunch time in his home art studio where he brings to life whatever inspires him — whether its the town’s historic buildings, structures he has encountered on his travels, portraits, florals, or commissioned work of beloved pets.
“I tend to think of myself as almost keeping a diary,” he says. “Every day, whatever catches my interest, I make a drawing or do a reference photo and then I paint a painting every day.”
Though his career was spent working in public relations, Bailey has been an artist since he was in kindergarten and won a regional public school art competition.
While studying philosophy and French in university, Bailey attended night school at the Ontario College of Art and Design to hone his craft through life drawing classes. (One of his many stories includes that about the nude model who drank whiskey out of a Coke bottle while working, but that’s a story for another time.)
“The reason we paint the human body is because it’s the most difficult thing to get right — and faces are a similar thing. We all have a body and a face, and we know it so well that if it doesn’t look right in a painting, it’s immediately apparent,” he says. “That’s primarily, I think, the reason that life drawing is so important as a foundation in drawing and painting.”
Bailey also notes how the flexibility of the human body makes it a dynamic subject for painting. This is what makes it interesting for Bailey, a Montréal Canadiens fan, to frequently paint hockey players, including moments of the recent 2025 Four Nations Face-Off, and, prior to that, a series on goalies.
“With their masks, modern goalies almost look like some of the ancient Roman warriors,” Bailey says, comparing them to historical paintings of gladiators in battle.
“For me, in a sense, the goalie is that warrior because in the hockey game, the whole idea is to get the puck into the net. The goalie is the last person to deny the player, so if the puck goes in it’s a disaster but if the goalie stops it, it’s a triumph,” he continues. “They get into poses that look defiant, and they make saves that look acrobatic. Plus, the uniforms are so colourful, so that spectacle is like a warrior spectacle which it’s really intriguing to me.”
For the past 15 years since he has been retired and turned to painting professionally, Bailey, who is a sixth-generation Port Hoper, has been documenting the town, capturing the important vistas and buildings in an “expressionist” style like that of 17th-century Dutch painter Frans Hals.
The portrait artist, Bailey says, could paint the glove on a person’s hand in three strokes.
“I was inspired by that idea of seeing how little you could put on the canvas to convey a lot,” Bailey says.
He adds that the goal is not to make the image “photo realistic.” Instead, it looks abstract when the viewer stands too close, but when they stand further away, their brain “completes the image.”
“For me, there’s a magic in that because you, as a viewer, have to participate in the painting, and that makes it much more interesting and, for viewers, much more exciting,” he says. “For me, it’s more important to involve the viewer and the way I want to do that is by doing this in an abstract, expressionist kind of way.”
In addition to painting the town, Bailey, who published a children’s book Charlie Meets the Goomby in 1977, has also used his writing to bring the stories of Port Hope to the community. In 2011, he self-published Port Hope Heroes, inspired by notable characters in the town’s history.
“I wanted to illustrate the stories, and retell them in a way, because I was afraid that they would be lost, and I wanted to set it down in a record of what some of the most interesting stories were,” he says. “And there were some fabulously interesting stories.”
When he’s not painting or writing about the town that inspires him, Bailey also takes on commission work, including for living and deceased pets.
“One of the things that a painter can do is make a painting that is a memory of the pet, but it goes beyond that so is not just a photo. You try to put some life into the painting so that when they look at it, it’s not just an image, but a feeling of what the pet meant to them,” he says.
“I ask them to tell me stories and when people start to tell their stories, life takes on a whole richer meaning. So, I ask them the dog’s name, what they liked about the dog, and their favourite memories, and, before you know it, you’re getting this complete picture of the pet. So it’s really quite special.”
Though he’s been painting daily for 15 years, Bailey never runs out of inspiration.
“Each day really depends on the things that I see and on the days that I don’t go out or I haven’t gotten an idea, I sometimes circle back to one of my favourite images and redo something I did ten years ago. It’s always neat to see how much I’ve learned and how much I’ve improved,” he says.
“The objective is always to do more with less — fewer and fewer strokes — so I’m always in pursuit of that, and it’s fun to keep trying.”
