From skateboarder to famous street artist, Shepard Fairey has seen the inside of numerous police cells in his long career. This week his ubiquitous portrait of Barack Obama, which appeared on billboards, T-shirts, hats and magazine covers throughout the 2008 election season, was acquired by the National Portrait Gallery in Washington.

Until he came up with his Obama image and went on to be named “Icon Maker” of the year by Time magazine, 38-year-old Fairey was best known for his rock-music album covers and an advertising campaign that featured a wrestler named Andre the Giant.

The artist’s most recent arrest was last August when he was in Denver for Mr Obama’s nomination to stand as the Democratic presidential candidate. He was busy postering an alleyway with some friends while a film crew documented their work, when riot police showed up. Fairey, who is diabetic, recalls how he and his fellow street artists dropped their posters, brushes and buckets of paste and legged it down the alley, only to be confronted by five paramilitary-style police pointing guns at their heads.

“I guess we got too close to the hot zone down town,” Fairey recalled as he waved a pretend gun in imitation of the cops: “Get on the ground or we’re gonna kick you in the head … We were quickly zip-tied and taken off to jail.” He spent the night in a cell with some anarchists and was fed the favourite snack of all American teenagers: “peanut and jelly sandwiches”.

Fairey graduated from the Rhode Island School of Design and went on to found a design studio which specialised in “guerrilla marketing”.

While Mr Obama was accepting the Democratic nomination, Fairey, out of jail with a slap on the wrist, was already filming a YouTube account of the 14th arrest in his meteoric career as America’s foremost street artist.

The story of his famous Obama portrait, a large-scale, mixed-media stencilled collage, is already taking on the mythic qualities of a quintessential American narrative. Emerging from humble beginnings in the back alleys of Los Angeles, the portrait became an instant sensation, a pop culture “icon” that was willingly embraced by the Obama political machine.

Before the President-elect swears his oath of office on Abraham Lincoln’s personal Bible, the portrait has become part of the Smithsonian’s permanent collection at the National Portrait Gallery, which is conveniently only a few blocks from the White House. Fittingly for the narrative of change, the Obama portrait was donated to the gallery by the head of Mr Obama’s transition team, Tony Podesta, and his wife, Heather.

The striking resemblance to the Che Guevara portrait which has decorated generations of student bed-sits, has not been dwelt on. But a little way from where Fairey’s portrait will hang there is a small portrait of the Cuban revolutionary by Charles “Chaco” Chavez, drawn from the famous photograph by Alberto Korda.

The portrait gallery is better known for its stuffy collection of George Washington portraits than street art, but the museum’s curator, Carolyn Kinder Carr, said simply: “We all fell in love with it. We always like portraits that reflect a particular moment in history, and we like the fact that it is an image that resides in popular culture.”

It’s not the first time that street art has been brought in from the cold, she noted: “The posters of [Henri de] Toulouse-Lautrec are essentially street art.” And there seem to be few bounds to Fairey’s capacity for self publicity. This week, for example, it was announced that he has donated a new image to, to promote the cause of rescuing street mutts. Mr Obama is hoping to adopt a pet from a shelter for the White House.

Fairey explained that he is “a big believer in speaking up for all who suffer injustice, regardless of gender, race, sexual orientation or, in this case, species!” He created a limited-edition run of 400 signed and numbered silk-screen prints in honour of a dog he had as a child growing up in Charleston, South Carolina, a mutt named Honey.

At the portrait gallery, meanwhile, the director, Martin E Sullivan, intoned: “This work is an emblem of a significant election, as well as a new presidency. Shepard Fairey’s instantly recognisable image was integral to the Obama campaign.”

Fairey’s collage became the central portrait image for the Obama campaign and was initially distributed as a limited-edition print and then as a free download. His other works are in the collections of the Museum of Modern Art, the Los Angeles County Museum of Art and the Victoria and Albert Museum.

The new portrait will be hanging at the gallery by 17 January, three days before Mr Obama’s inauguration. Suitably enough it will be in the “New Arrivals” section on the ground floor.

Leonard Doyle
The Independent