Shepard Fairey is a designer, political activist and artist best known in the last decade for creating the iconic “Hope” poster for Barack Obama’s 2008 presidential campaign.

In the late 1980s, he became an underground sensation, traveling across America with his cryptic “Andre the Giant Has a Posse” stencils, and “Obey” imagery lifted from John Carpenter’s cult sci-fi film They Live.

Fairey, 44, was in Toronto this week to unveil two murals. It’s part of a tour sponsored by Hennessy cognac, for which he designed a limited-edition bottle. One mural is located in an alley on Queen St. W. beside the club Tattoo (567 Queen St. W.), where he also performed a DJ set Thursday night. The other is on the back of the Gladstone Hotel(1214 Queen St. W.). Here are a few things we learned about him.

He embraces social media, but craves the human connection

It used to be that as a street artist, the only way to make an impact was through volume and visibility. “You had to be incredibly prolific,” Fairey says. Hence the rampant tagging, stickers and stencils you might see in the city.

Times have changed with blogging and social networks, where artists get hooked on the validation of fans “liking” their art. But while Fairey uses the Internet to promote his work, his favourite part about making street art are the encounters with the passersby. “I’ll hear them after, saying ‘holy crap, I can’t believe this just popped up! What’s the story here?’ The visceral impact is completely different from the buffer that social media interface creates.”

He owes his career partly to Kinko’s

Fairey took the Kinko’s slogan “Your Copy Store” quite literally. He would go in late at night and take over the floors, making it his studio. The 24-hour copy shop also was partly responsible for his red, black and white motif. He managed to MacGyver colour photocopiers with a paperclip to give him free product in those colours. His limited budget also forced him to focus on a style, which essentially became an advantage.

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He fears Led Zeppelin fans the most

Fairey is working on posters for The Rolling Stones’ upcoming South America tour, and the band Interpol. But the most memorable rock project was possible when Led Zeppelin approached him to design album packages. “They have a much bigger audience than I do. With that comes the danger of the person who has been a fan for 40 years who says, ‘That’s not right for Led Zeppelin.’ It’s a delicate situation. I think I’d most likely be killed by a sycophantic fan of theirs.”

He succeeds through relentless trial and error

Fairey doesn’t tend to dream up an amazing vision, getting up by candlelight, putting on his beret and painting in his sleep. On the contrary, “it’s blue collar work ethic. Try this, try this, doesn’t work, doesn’t work, ah this works. The same thing applies to my DJing and learning song combinations.”

He operates a successful clothing line

Fairey is creative director of the multi-million-dollar Obey Clothing line where he has a hands-on involvement with all the visual imagery used on t-shirts and apparel. He says that mass-producing defiant shirts was always part of his plan but the street art took off much faster, allowing him to leverage his reputation when the timing was right.

“I’ve always looked at fashion as something potentially awfully shallow, but something that everyone is concerned with. It can be a dark impulse or a creative impulse. It can go either way, but it should be channeled in the best direction possible,” he says.

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