I’ve never met Shawn O’Keefe, but we have an odd connection. He created a caricature of me as “The Dude” in a bathrobe for a how-to column in TransWorld SNOWboarding magazine. Over the years I guess I taught him about random and amusing snowboarding tips. He always spit back with comical cartoon drawings to match. See, Shawn is part of what we at TransWorld joke is the Canadian underground art railroad—a fictional portal that’s led other creative Canucks like Randy Laybourne, Dustin Koop, John Antoski and the Callahan brothers to the sunny shores and art directing gigs of Cali and beyond.

What pulled O’Keefe into designing in the board, bike and related communities? “It’s just always worked out that where—in my eyes—the best, most rad, most fun art has been at the fringe of society,” O’Keefe says. “The people that choose these activities as their life and livelihoods march to the beat of a different drum, they aren’t afraid to take chances. The underground communities, clubs and publications that support these pursuits also just happens to be where this kind of art thrives as well.”

The kind of art that O’Keefe refers to is broad. His go-to mediums are pen and pencil, acrylic and aerosol, but his talents touch just about any medium, from screen-printing to music.

Shawn works as a freelance designer and illustrator in Victoria, BC, under the guise Trust 36 for his one-man band, Artificial Flavour Graphic Engineering Company. He has a broad spectrum of focus, everything from logos, illustration and fashion design to packaging and soundtracks. He’s created one-off, wood-looking shades for Oakley, beer labels, snowboards, skate wheels and more. He is also one of three members of the Woodpile Collective, a creative collaboration with fellow Victoria artists Blythe Hailey and Sean McLaughlin.

Drawing on the lush, robust, natural environment of Vancouver Island, O’Keefe has a penchant for creating forest and landscape works that capture the islands mist, light-slivers and verdancy. “My nature-based work is completely about soaking in my environment,” he says. “Getting out in the elements, getting wet and muddy. Hiking through the bush and staring out into the crashing ocean around a campfire. I try to evoke that feeling through the work, not so much rendering the scene exactly as it looks. I shoot for capturing the most that I can with the broadest strokes.”

Shawn’s misty forest scenes are as natural a fit for his environment as they are for the mountain biking community—the promise of a swooping trail ahead through a sometimes-dark forest or pedaling after that last sliver of light towards home. He grew up in the Cowichan Valley of Vancouver Island with his parents and little sister, went to high school in Duncan and College in Nanaimo before settling in Victoria. Although the North Shore now has a legendary reputation in mountain biking, Shawn’s experience with bikes has mostly been pre-mountain bike. “As a kid I lived in the woods and dirt roads surrounded my home,” he says. “I had a small group of friends who all had weird hybrid BMX street-bike banana seat things…basically they had two wheels. We had a bike gang called the Westcott Devils. We made t-shirts and had a treehouse and stuff. Then my bike was stolen while my friends and I were swimming at the river. I was devastated. I then made a fatal error of listening to my dad when I was able to buy a new bike. He talked me into getting a touring bike—he said it was a more grown up bike and that I wasn’t a kid anymore. I could hardly ride the thing! Keep in mind I lived on a gravel road and the tires were like dinner plates. That pretty much ended my cycling experience. Now I just live vicariously through mags and the Internet. It’s hard to believe some of the amazing feats accomplished in the short time it’s [mountain biking] been around.”

When it came to creating this issue’s cover, his first for Freehub, to compliment Paris Gores shot of Katie Holden in Vantage, WA, it was initially a “How the f-ck am I going to pull this off” kind of feeling, he says. Although O’Keefe is well versed in many mediums, this was the first time he’d worked his style into a photo. “The image captures the reality and beauty of the moment and my illustration expresses the creativity and imagination,” he says. I experimented a lot with hand drawing elements on paper and scanning them into composition together in the computer. I played with lots of textures to bring in more of my painterly style.”

Maybe it’s just O’Keefe’s use of aerosol that that draws graffiti association in his other works. It’s subtle in some works and apparent in others, all refined into a beautifully unique style. “I was fairly involved in graffiti in the late nineties and working with aerosol,” he says. “learning the art of cutting with cans, layering, working on can control and pushing the limits to where you experience art. I also create in an art collective [The Woodpile Collective] where we not only put art in the streets but put it in the woods, on beaches, et cetera, trying to expand the studio and gallery out into the environment. These things all work back into my personal work. The nature of aerosol fits so nicely with a rainforest’s atmosphere of fog cloud and steam…the arm movements and the tag styles all work so nicely with the structure of branches and the forest floor. Just a natural fit of style and environment I suppose.”

All artists are tied to the process of creation and all have a different approach. “I guess it’s a bit like making a good soup,” he says. “You let the ingredients simmer and you build a nice base. The magic seems to happen when the work has been done.”

Sometimes the soup sells, sometimes it sits. The artist’s way is not an easy one. When it comes to getting by Shawn says, “I’m personally not a believer that others around me should pick up my tab while I work on my craft. My goal has always been to take care of myself and my family with my art and work hard to get there. People are quick to say ‘You’re so lucky too be able to make art like that, and sure I feel very fortunate to be where I am, but I also know how much time I’ve put in.”

When he’s not in the studio or dropping rogue pieces of art around town with his Woodpile crew, Shawn’s spending time with his wife and two boys showing them what they can do that doesn’t involve a screen, taking themcamping and playing music. “There really isn’t a lot of time in my life for things that aren’t creative in some way. That’s kind of my thing. I’m looking forward to drinking some tequila by a pool somewhere warm in the not so distant future. That would be good.”

And for hopping on the art railroad and moving to California like his fellow artisans? “Only for those crazy visits to see my southern brothers, where I punish my Canadian liver with amazing American craft beer. Then I fly back home to drink maple syrup and run with the beavers.”