McKevlin’s Surf Shop, Folly Beach. February 15, 1984. Something clicked. “I remember it clearly,” says Shepard Fairey, the famed street artist best known for his ubiquitous “Obey Giant” oeuvre. “It was my 14th birthday. I was getting my first skateboard, and a Skate Visions video was on while I was waiting. Agent Orange was playing on the soundtrack, and between the euphoria of getting my first board and the exhilaration of the music, I had this epiphany. This is what I wanted to do with my life.” Fast forward 25 years to a busy January and February 2009, including the unveiling of Fairey’s iconic Obama Hope portrait in the permanent collection of the National Portrait Gallery in Washington, D.C. and a Shepard Fairey solo retrospective at the Institute for Contemporary Art/Boston. It’s been a hell of a ride, but arguably, Shepard’s kickflip into the consciousness of our nation at a pivotal moment can be traced back there, to McKevlin’s in 1984 and the raucous tunes of Agent Orange, and certainly to the sidewalks and narrow streets of Charleston. Suffice it to say that 25 years ago, Shepard’s exasperated parents—his mother, Charlotte, and his physician father, Strait—never imagined their skateboarding son would play a significant role in an historic election. Or have his work in the National Portrait Gallery. Or, quite frankly, that he’d be doing much of anything that might be deemed “constructive”—at least by the prevailing Southern standards of the Reagan era. “It was a rough road, believe me,” Charlotte attests. “Shepard definitely marched to a different drummer.” Wheels Turning Despite being a self-described “pretty conformist, mildly mischievous young kid” who learned to lindy at cotillion and excelled in art class at Porter Gaud, Shepard, by age 14, began to itch under the collar of his prep school coat-and-tie confinement. “I felt cornered and oppressed; I felt disconnected from school and the team sports that my parents encouraged. Nothing was giving me that visceral feeling of enjoying being alive,” he says. Then he discovered skateboarding. “I could go out the front door and be on my own,” says Shepard, whose McKevlin’s moment didn’t make for easy teenage years in the Fairey household. “My dad’s a stubborn perfectionist, and so am I; it just manifests in different ways culturally. It was never in his nature to dissuade me from my commitment, but there was tension between us in high school. My parents had a definite idea of how things should be,” recalls Shepard. “There was a sense of tradition and social structure in Charleston that they subscribed to and didn’t want to upset.” Shepard was a kind, clean punk. “He never drank, smoked, or did drugs, so we didn’t worry about that,” claims his mom. “He just defied the status quo; he tested everything,” adds his dad. Their rebellious young son didn’t score any points when someone from church complained about him skateboarding on the sidewalk. Or when he was arrested for skating at the Market (his first of some 15 or 16 arrests to date). Nor did the bristly punk aesthetic favored by Shepard and his fellow skate rats jive with strict Porter Gaud standards and the South of Broad preference for duck prints and decorum, at a time when “alternative” wasn’t yet in the Charleston vernacular, or really even an alternative. In fact, the punk scene was still so peripheral on the peninsula that there was no place to buy T-shirts and stickers to go with his blue Vans sneakers and his neon pink Tony Hawk board, so the budding artist started making stencils for homemade T-shirts of The Clash, the Sex Pistols, and other misfit bands. He used his mom’s business copier to create stickers from skate magazine graphics, which he then plastered over his board, his “Shepmobile” wagon, and everything else. Giant Strides After transferring to Wando High School, Shepard found a more diverse peer group but still managed to confound expectations. “Skaters thought it was weird that I was in honors classes, and the honors students thought it was weird that I was a skater,” he says. He continued after-school art lessons with his Porter Gaud teachers and, after his junior year, enrolled in a summer program at the North Carolina School of the Arts, from which he was expelled for sneaking out at night to skate. Strait and Charlotte Fairey were at their wits’ end. “Son, you’re disrupting our household. You’ve got to do something constructive,” his dad said. They sent him off to an intense art school in California for his senior year, and from there, he was accepted to the Rhode Island School of Design (RISD). During the summer of 1989 after his first year at RISD, Shepard was working at a Providence skate shop and continuing to create original tees and stickers when a picture of pro wrestler Andre the Giant caught his eye. He made a stencil out of the image, adding the words “Andre the Giant has a Posse” in one corner and Andre’s impressive specs: “7'4"” and “520 LB” in the other. The sticker started out as an inside joke, a turf-marker among his skateboard “posse,” but Shepard became increasingly intrigued by the evocative power of a mysterious, ambiguous image—simultaneously sinister and goofy—placed randomly and anonymously in the public sphere, with no apparent agenda. Energized by both mischievousness and an astute artistic and intellectual curiosity, he began sticker-bombing all over Providence, then on to New York, Boston, and beyond. He mailed stickers to friends and fans around the country, and Andre proliferated, street corner to street corner. Along the way, Fairey branded Andre with the Orwellian tag “OBEY” and his black-and-white iconic giant grew huge—into viral art that spread to lampposts, billboards, and vacant warehouses across the globe. With savvy and intention, and a daredevil’s drive to scale tall buildings with long brushes and buckets of wheat paste, Fairey took his skaters’ inside joke and turned the punch line inside out—encouraging viewers to confront assumptions about art, consumerism, and who controls messages in the public realm. “Shepard is the grandfather of populist street art, which is a funny thing to say about someone not yet 40,” notes contemporary art scholar Mark Sloan, director of the Halsey Institute of Contemporary Art at the College of Charleston, which presented a Shepard Fairey exhibit in the late 1990s. “He created a phenomenon with his ‘Obey’ series, tapping into something that became bigger than even he imagined. His brilliance was using this nonsensical image to lead people to question what they see. He’s a master at taking iconic images and swirling them together to create a new image that challenges our perception.” Guerrilla to Gallery While never abandoning his populist passion or his guerrilla street art roots, Fairey has developed a varied body of work, including mixed media, album covers, movie posters, and screen prints of rock stars and revolutionaries. A provocative, constructivist look is his unifying aesthetic and “question everything” his underlying motif. “I like artistic problem solving, the challenge of making a statement and having it be visually arresting and appealing,” notes Fairey, who now lives in Los Angeles with his wife, Amanda, and two daughters, Vivienne, age three, and Madeline, 15 months. He and Amanda, an artist and jewelry designer, met in San Diego in 1998 and were married at the Governor Thomas Bennett House in Charleston in 2001, as, appropriately, “Rebel Waltz” by The Clash was played on classical guitar and harp. As the consummate blurrer of boundaries—whether between country clubs and skate ramps, street art and fine art, capitalist critique and commercial venture—Fairey represents the epitome of artistic and entrepreneurial diversification. Just as his Obama poster masterfully melded red and blue, his cultural and artistic approach is about bridging divides, balancing the beautiful and the provocative. Fairey has had major gallery shows in New York, San Francisco, and London in the last three years, all resoundingly successful, selling out in short order. And he continues to evolve his “Obey” project and produce other fine art under the “Obey Giant” umbrella, while he and Amanda also own and operate a commercial graphic design firm, Studio Number One, with clients such as Pepsi and Saks Fifth Avenue. “The studio has allowed us to create our own little utopian ecosystem,” says Fairey, noting the studio’s offshoot Subliminal Projects gallery that grew out of an artists’ cooperative and promotes the work of renegade and innovative artists. Both his commercial and personal endeavors involve substantial philanthropic work that Shepard donates to numerous causes, including environmental groups. Perhaps it’s only fitting that an artist who advocates “questioning everything” gets his share of questioning these days. Some critics claim he’s sold out and lost his street cred by doing commercial work, while others, such as the Associated Press, argue that his reappropriation of images constitutes plagiarism. But Fairey, along with numerous art experts like Mark Sloan and Jill Medvedow of ICA/Boston, find those claims not only bogus, but insulting. “If anything, I’ve reaffirmed my street cred,” says Fairey. “My effort has always been about empowerment. The Obama poster was a genuine grassroots effort that made a difference. Not every artist who wants to comment for or against a political figure [by using their image] can commission an original portrait. I see this as essential to First Amendment rights.” (Go to www.obeygiant.com for Fairey’s full stance on the pending AP lawsuit). “Shepard has kept a gritty limited palette his whole career. He’s always liked the graphic, slightly CBGB look: collage combined with a strong centralized image,” says Charleston artist and longtime friend Tim Hussey, a former skating comrade and fellow Porter Gaud and RISD classmate. “He’s very deliberate, a master at editing. He enjoys reappropriating images that were signs of the times and saying, ‘Here, take a look again.’ His true medium is to allow us to draw ourselves through the imagery he presents.” Perhaps that’s where the controversy comes in. Fairey is daring, roguish, and comfortable with ambiguity; he actively resists categorization, but most observers like clarity; people in general feel safer with neat and tidy boxes. It’s easier to blindly obey than to jostle our assumptions and think for ourselves. Mark Sloan enjoys the irony: “It’s an exquisite paradox—Shepard’s the quintessential underground artist whose studio is now designing logos for Saks. He’s bankable, one of the most celebrated unknown artists out there.” Four-Letter Words Indeed the irony and symmetry of Shepard’s recent renown has an artistry in and of itself. His outlier “Obey” campaign may have put him on the art world radar, but his current mainstream notoriety (à la features on CBS Sunday Morning and The Colbert Report, being named one of Rolling Stone’s Top 100 Cultural Icons, his ICA show, and the delicious irony in the mayor of Boston inviting him to plaster public murals all over the city where he was arrested for doing just that) rises in large part from yet another four letter word. In fact, “HOPE” may have been Fairey’s operative word all along. Hope was behind his adolescent epiphany at McKevlin’s and his love of skating, behind his relentless sticker obsession, and his continual hard work and artistic evolution. Hope for freedom—the freedom that he found in skateboarding and punk rock music, freedom of expression, and artistic freedom to reappropriate and reinterpret public images. While his stickers and street art may get cleaned up by graffiti police in a matter of days, Fairey’s artistic legacy and impact is lasting. “He’s opened the door to provide a voice for underground artists,” says Sloan. “Shepard’s provided hope that they can get their work out there and get it seen.” So maybe all those underground artists owe Charleston a debt of gratitude. “If I had grown up in California with lenient parents, I would never have had to develop the backbone to express myself and stand up for what I believed in,” says Fairey. “Charleston forced that—it made me draw a line in the sand and say, ‘This is who I am.’”