Shepard Fairey’s boyish looks are deceiving. Perched on a ladder in a Black Flag T-shirt and Adidas shell shoes outside of Eye Level Art’s gallery, he still resembles a 20-year-old skateboarder with a rebellious streak and impish smile. But Fairey has evolved since he first picked up skateboarding on the streets of Charleston more than 20 years ago. He has grown from a defiant teen plastering road signs and parking meters with anti-propaganda stickers into a nationally known artist and designer.

Fairey captured the country’s attention in 2008 after creating a poster of then-presidential candidate Barack Obama, which many argue became the dominant symbol of his campaign. Despite his success with political posters and corporate design — Fairey has worked with a few big names including Pepsi, Kobe Bryant, and Led Zeppelin — he hasn’t abandoned the street style that set the course for his artistic reputation.

“I still enjoy doing street art even though I’m getting older and I have kids and I’m on probation right now, so I have to be very careful,” Fairey says. “I still enjoy it. I like to see the process, seeing it come together on the street whether it is a quick hit or planned.”

Fairey, who has been arrested 14 times in his career, is currently on probation after pleading guilty to three charges of vandalism in a Boston municipal court. But the run-ins with the law haven’t stopped him. During a recent visit with his family, who lives in the area, Fairey heeded the request of Eye Level proprietor Mike Elder and added one of his signature pieces to the outside of the Spring Street gallery. The work was legal and highly encouraged by Eye Level’s staff.

After beginning in the late afternoon, Fairey completed a wheatpasted “Mujer Fatal” mural, an original design from 2007, on the old warehouse by dusk. The artist used screen-printed squares of his posters as tiles for the mural, layering one on top of the other to give the work depth and texture. For an adherent, Fairey used a substance similar to wallpaper glue, which he says dries quickly. By the end, the glue coated Fairey’s hands and clothes, but he didn’t seem to mind. He looked comfortable using his hands to smooth the posters and fill the crevices and nooks of the old edifice.

Fairey is admittedly a perfectionist, frequently stepping back from the wall to get a full view, then ripping off a scrap piece of black paper to fill in a hole. But when he isn’t working on a planned piece, the process is fast, one he developed when he was more likely to put up his work without prior consent. His planned murals take a while longer. Many times, he says, someone will post on Twitter or Facebook that he is working on a new public piece, and a group of onlookers will show up. A few fans trickled out to the sidewalk in front of Eye Level and chatted with the artist as he worked. They discussed the skating scene in Charleston and old T-shirts Fairey created. The shirts, he joked, were limited edition with only 200 in production — not an attempt to make them more valuable, but because no one wanted them. The small band also joked with Fairey after he wobbled on top of his ladder, reminding the artist of his fall in Banksy’s documentary Exit Through the Gift Shop.

Fairey says he doesn’t mind talking to people while he works. He likes the social aspect, which fits with his belief that street art is a democratic process.

“When you engage in street art, you have to understand that the work is in public and that’s great. It is very democratic, but that also means someone else can do something over it,” he says. “That is the great thing about street art: You don’t go through any bureaucracy. The public then has the ability to have a dialogue with it, comment on it by putting their own work over it, or criticize it.”

Several of Fairey’s public pieces have been targeted as of late, including a mural on Houston Street in New York, which was tagged by graffiti artist NAW within hours of completion. Some call the tags vandalism and the culprits criminals — NAW was chased by a security guard who tried to apprehend him — but Fairey sees it more as a casualty of the business.

“It’d be great if they were attacking Goldman Sachs’ headquarters instead of my piece, but I love what they are trying to say,” Fairey says with sincerity. “I’ll always be more supportive to what they’re saying than the powers that be.”

Fairey’s unique position as an artist might have inspired some of the recent attacks. Although he originally made his name in graffiti and street art, Fairey started a design and marketing company called Obey Giant and has created logos for celebrities, the movie poster for Walk the Line, and the cover for Led Zeppelin’s greatest hits album, Mothership. As a result, he’s caught flack from the guerilla art scene, particularly clandestine artists who think he’s sold out.

“I’m too street for the conservative world and too corporate for the street world,” he says. “I’m in this interesting no man’s land that is a result of me really trying to break down a lot of these barriers that I think are unhealthy.”

Perhaps it is a result of growing up, or the reality of having to make a living and support a family, but Fairey is trying to expel some of the negative connotations of the marketing world. Advertisement and marketing, he says, “is where a lot of artists and designers get a creative outlet, and not all products are evil.”

Nevertheless, it seems ironic that his anti-propaganda campaign, Obey Giant, now represents his marketing company. But Fairey looks at it with a more holistic approach. It’s cyclical, he says. “It’s like every teenager rebelling against their parents — eventually you realize they had solid advice. I’m 40 now, so I went through that period in my life where I felt very much it was me against the world. I had nothing to lose being as obnoxious or transgressive as I wanted to be.”

Age has not stopped Fairey from including social and political messages in his compositions. Rather, he has become more political over the years. Through his work, Fairey says he has always urged viewers to question social conventions and the agenda behind messages they receive, though the war in Iraq and George W. Bush’s presidency inspired him to tackle specific issues.

“Bush being elected at all and then again made me really look at how politics work in the United States, corporate funding about things between Halliburton and Dick Cheney and George Bush,” he says. “Once you open Pandora’s box and you are aware, it is almost impossible, for me at least, not to feel like I have to make art with issues that maybe aren’t getting enough attention.”

Fairey tries to get the message across without preaching to his audience. He says he tries not to be a downer either.

“I wanted to make images that have a sense of humor, maybe even beauty, to grab someone’s attention in a visceral way that will make them care about what the message is,” Fairey says.

This urge has led him to tackle issues like the conflicts in Darfur and Burma. Fairey recently completed an image of Aung San Suu Kyi, a Burmese opposition politician, whom he believes is a naturally compelling and positive person.

“People who live their lives righteously are good role models I think I’d like to put on a pedestal visually,” he says.

For the future, Fairey has no set goals. He says he has to “maintain the machine” now, pay his employees, and keep his operation going. Yet he wants to experiment, fail, and try new formulas. He’s also planning to make a return to Charleston. Fairey has been working with Mark Sloan from the Halsey to plan a street art show for Spoleto 2014. Fairey is looking to not only participate but also curate the show.

“I think the cool thing about Spoleto is it brings so many different people to the city. Charlestonians enjoy it, and there is a really great cross pollination — that is an exciting time to be involved in something here.”

Fairey hopes the art scene in Charleston continues to expand past its traditional landscapes and wildlife art. He’s optimistic, as galleries like Eye Level Art offer more pop and street art.

“Of course, we appreciate the traditions, but we need to realize that new traditions can be built,” he says. “Just because it doesn’t fit the mold doesn’t mean it doesn’t work.”

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