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W hen Patrick McNeil was a high school freshman in Arizona, he regularly traded notebook sketches with his friend Patrick Miller. Their subject matter was typical teen angst: underground band logos, alternative superheroes, and other emblems of adolescent escapism. Though they went separate ways to study art in college, McNeil and Miller reunited in New York City by the end of the 1990s, working with a female poster artist from Japan, Aiko Nakagawa. During a short stint in jail for pasting Do-It-Yourself (DIY) screen prints illegally on city walls, the trio came up with a moniker for their work: FAILE.

"We really liked the idea that you could fail to succeed," says McNeil as a way of explaining the name's origin. (FAILE is also an anagram of "A Life.")

Eventually, Aiko left, leaving McNeil and Miller to transform FAILE into one of the most recognizable crossover names from the street art world. Their style is a kaleidoscope of stenciled and silk-screened pop-culture images, cryptic ad slogans, and abstract neon shapes, all ripped and scratched in a hyper-refined style that will be as close as many in the art world will ever get to real street art.

More than a decade after its inception, FAILE received a commission beyond most young street artists' wildest dreams. Tasked with creating artwork to open the Lincoln Center's New York City Ballet (NYCB) art series, McNeil and Miller took street art to its most baroque extreme, constructing a 40-foot tower of small wood blocks and rectangular pallets, emblazoned with thousands of icons sourced from comic books, B-movie posters, and 1950s pinup magazines.

The NYCB opened its archive to the artists, who transformed vintage depictions of Tanaquil Le Clercq, the ballet company's most celebrated dancer from the 1940s, into a kind of Wonder Woman, her glowing wingspread stenciled with a coterie of neon colors that suggested not superhuman physicality so much as the crushingly unstoppable ascendency of DIY culture. How you feel about that is entirely your choice.

When FAILE silk-screened a waifish Goth down on her knees, arms covered with vine-like floral tattoos and wrapped around the calves of a ballerina standing en pointe the message could not have been clearer: Street art, once the artistic voice of the anti-establishment, has been absorbed by the establishment.

When describing the origins of street art, it's difficult to know where to begin. Seymour Rosen's book In Celebration of Ourselves (1979) chronicled folk-art environments, handmade signage, and gang communications on walls throughout blighted Los Angeles during the 1960s and 1970s.These efforts in DIY were decidedly apolitical, most coming out of first- and second-generation immigrant culture.

A late 1960s Philadelphia artist named Cornbread is often given the title "Father of Graffiti Art," his spray-painted signature setting the stage for graffiti's first explosion. Indeed, an entire generation of self-taught artists discovered each other in hip-hop and punk-rock clubs and then found their voices tagging subway cars, businesses, and myriad walls all over New York City in overt political strokes. The increasing elasticity with which these artists painted their names became more and more codified to the point where, if you didn't know the lingo, you couldn't read the walls at all. With this sense of "otherness," graffiti became synonymous with vandalism in New York and most urban environments.

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Even during these elusive times, street art yielded its share of crossover talent. Jean-Michel Basquiat, Keith Haring, and Kenny Scharf all started out spray-painting public spaces, only to end up, in very short order, among the elite celebrity artists of 1980s New York City. Basquiat died in 1988 of a heroin overdose, Haring in 1990 of AIDS. Scharf, to this day, continues making psychedelic pop art influenced by the street vernacular. Yet, by the end of the 1980s, the influence of graffiti and street art in the mainstream gallery world seemed to have run its course and returned once more to the underground.

As the Internet became commonplace in the 1990s, DIY culture and, with it, street art, began to make something of a comeback. Despite punk rock, new wave, and hip-hop all being absorbed by the mainstream record industry and slicked out into MTV-ready pop packages, underground music found new alternatives in hardcore punk, Goth, house music, and grunge. All of these nascent subgenres needed flyers and posters to spread the word, and the artists who created these DIY visual works were largely the latchkey children of the Woodstock generation, who'd been rechristened the "me generation" after a near-complete shift to conservatism happened during the 1980s. Increasingly educated, the children of the me generation were determined not to "sell out" like their parents had.

There was a rather inauspicious sticker created by a chubby art school student at the Rhode Island School of Design in 1989. His name was Shepard Fairey, and his image of WWF wrestler Andre the Giant became the conceptual icon at the center of the artist's phenomenological slogan "OBEY." The DIY campaign eventually launched Fairey from skateboard/art school geek into unexpected celebrity.

As OBEY stickers and wheatpasted posters of the icon popped up on payphones, park benches, apartment walls, and school playgrounds, the work took on meanings well beyond Fairey's initial attempt at provocation. The artist became not only the center of a growing form of guerilla communication but an in-demand commercial artist. "He is," says Angelo Madrigale, curator of the street-art division at the Doyle Auction House in Manhattan, "the biggest success story in DIY culture, bar none."

By the 2000s, the time seemed nigh for the post-boomer generation to make its entry into the political realm. Then 9/11 happened.

Almost overnight, revolutionary images went silent again. Amid the cry for revenge and the din of two wars blaring from televisions and radios across the world, the United States experienced a cultural crisis, unable to identify with the Islamic world in a civilized way. Yet, as the Iraq and Afghanistan wars became increasingly unpopular during the George W. Bush administration, a new boldness took root. By 2008, progressivism, liberalism, socialism, populism, and other forms of left-leaning ideologies, unified their voices around a young African American candidate for president, who just months prior was a relative unknown.

Many have argued that, had it not been for Fairey's iconic "HOPE" poster of Barack Obama during the '08 Democratic primaries, Obama might not have won the nomination, let alone the presidency. It sounds preposterous, even hyperbolic, but consider the barren decades of 20th-century art that failed to produce even the smallest of heroic portraits.

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The cubists fractured the images of their patrons and lovers; the surrealists erased their heroes and left us with a civilization devoid of myths; the abstract expressionists, reacting to the atomic bomb and the threat of nuclear annihilation, splashed canvases with paint strokes fueled by anxiety and youthful energy. But the hero was nowhere. Even when pop artists like Andy Warhol evoked the image of a celebrity or head of state, it was hard not to read a sense of irony, even tragedy into their Day-Glo imagery.

Yet there stood Fairey's Obama, compact like the face on a government currency. Its heavy red contrasts on the right side of the image conjure the seriousness and boldness of the early 20th-century Soviet poster style. As these reds casually yet permanently flow into the soft blues across the left contours of the candidate's face, Obama's resoundingly optimistic upward glance envelops the viewer with a sense of ideological promise, a rebirth of ideas as much in art as in politics.

You could barely walk down the street that November and not see windows lined with the image. Weekly newspapers reproduced it on eight-by-ten-inch cardboard stock as inserts leading up to Election Day. Eventually the Obama campaign adapted it as the centerpiece of its visual PR in headquarters across the country. Believing that a good poster was among the least constrained ways to gain access to a social world beyond the boundaries of his own, Fairey gave street art something of an apotheosis in that moment. Yet all was not well.

The Associated Press sued Fairey for use of one of its copyrighted photographs of Obama as source material for the poster. Despite his defense that appropriation was well within the limits of copyright law, provided the image was sufficiently altered from its source, Fairey was, in a twist of irony, slapped with a $25,000 fine by the new president's Justice Department.

When one door shuts, another opens. Following the 2008 global financial crash, several new movements emerged to challenge the ineffectiveness of government and, in particular, the notion that the U.S. banks were "too big to fail." On the right, the Tea Party catapulted to political power in 2010, clamoring for increased austerity and tighter budgeting. It was, to be sure, just more extreme Republican rhetoric. What happened in the summer of 2011 was less expected.

Disgruntled by President Obama's lack of follow through on economic inequality following the recession, some 40,000 New Yorkers took to Zuccotti Park, near Wall Street, to protest the rampant cronyism that sank the economy. The Occupy Wall Street movement spread across the nation, where urban centers were lined overnight with tents and sleeping bags by the bohemian and the working class alike, proclaiming: "We are the 99 percent." It was a rallying cry not for austerity but for real reform aimed at righting the vast inequity between the very rich and everyone else. And Shepard Fairey was once again at the center of the visual commentary.

This time, his ad-hoc lyrical style applied to the image of Barack Obama was replaced by the mask of 17th-century British anarchist Guy Fawkes made famous in the comic book and subsequent film, V for Vendetta (2003). The message was no longer hope. It was revolution.

"Last time I was in Sao Paulo," notes Lois Stavsky, a street-art documentarian, "I brought a bunch of 'OBEY' stickers with me. They worship Shepard down there. The kids literally swarmed up around me to get their hands on them. It was amazing. He gives them hope."

Between the summer of 2006 and the fall of 2011, street art became increasingly popular with the museum establishment-major retrospectives were held at the BALTIC Centre for Contemporary Art and the Tate Modern (both in the U.K.), the Museum of Contemporary Art in Los Angeles, and the Museum Het Domein in the Netherlands. British stencil artist Banksy crossed over big time with his purported documentary, Exit Through the Gift Shop (2010), which depicted his deft conceptualist work as the justice-driven alternative to gallery-darling Damien Hirst's nihilism. "They say Banksy does stencils because he couldn't do graffiti," says Stavsky, who admits that some of the bigger names in street art are now emerging out of art schools rather than honing their craft on the streets.

No such criticism exists when it comes to Philadelphia's Steven Powers. A graffiti artist by background, Powers comes from the same home turf as street-art originator Cornbread. Powers's latest series, however, moves away from straight graffiti, instead mining the iconography of traditional hand-painted signage from mom-and-pop neighborhood store windows and lowbrow advertisements. In the mural piece Love Letters, Powers paints in thick red lettering: "Prepay Is On... Let's Talk Till My Minutes Are All Gone." Abstracted from promoting any particular brand of cell phone, the work becomes a commentary on the fragility of human interaction and the finiteness of life.

The street artist known as Swoon (née Caledonia Curry) is taking a different approach to activism. Swoon's Transformazium, an arts collective based in the all but abandoned Braddock, Pennsylvania (near Pittsburgh), provides classes to its impoverished locals, utilizing the steel town's derelict urban resources. "She puts her money where her mouth is," says Doyle Auction House curator Angelo Madrigale. "Just look at the work she's done in Haiti." Madrigale refers to Swoon's Konbit Shelter, a visionary project that artists and architects in Swoon's circle created in post-earthquake Haiti to educate and encourage locals in all forms of self-expression.

On September 29, 2012, the Barclay Center in Brooklyn opened its doors to the public, welcoming the Brooklyn Nets as its home NBA basketball team. The indoor stadium (partially owed by rap superstar Jay-Z) was mired in controversy from the outset for its role in getting the area around Atlantic Avenue in Prospect Heights declared blighted by city officials, a practice that paved the way for the stadium's erection. During its final construction, local graffiti artist José Parlá was commissioned to paint the center's massive entryway.

Though based in traditional graffiti, Parlá works in a strange calligraphic style that seems sourced as much from fine-art heavyweights like Mark Tobey and Cy Twombly as from the streets. "The process in my work is similar to that of the city," says Parlá, whose work makes the strongest argument for street art's growing cross-pollination with fine art, a notion long-rejected by artists working on the streets. (The fine-art world is traditionally "the enemy.")

Diary of Brooklyn, Parlá's mural for the Barclay Center, bears nothing of the narrative approach typical of public works. There are no people, places, or things from Brooklyn here. Instead, a rapturous layering of abstract graffiti lines splash and splay across a background of blue and gold layers of oil paint made to look like weatherworn decay. It's as if the city were still writing itself, the letters not quite formed, the language unfinished. Parlá's mural is abstract enough to transcend the Barclay Center's controversy with a largely apolitical work that seems indicative of most street-art pieces bankrolled by high-level patrons.

But not everyone is buying into it. Over in Queens, the sun goes down behind a tall structure known as the 5Pointz Aerosol Art Center, a central nexus of graffiti art in NYC. There, a spray-painted tag directly across the street from the Museum of Modern Art's PS1 reads: "Dear Artworld: When we inherit the earth … you aren't invited. Love, My Generation." It is an anti-establishment sentiment that many still think is central to street art's identity.

Meanwhile, up on 66th and Broadway in Manhattan, FAILE is putting together the second (and last) of its Lincoln Center installations for the center's May 29th collaboration with the NYC Ballet.

Eschewing the largesse of the FAILE Tower, the street-art duo this time delivers eight structures, each about ten-feet tall, featuring images of ballet dancers jumping off tall buildings, floating over the city skyline with burning umbrellas and being devoured by a pair of police officers with wolf heads. The most self-aware canvas in the new series depicts a wolf sitting deflated on an armchair watching TV in some humdrum suburban living room, the words "Retreat to the ordinary" emblazoned across the bottom.

The canine beast, once the savage emblem of FAILE's inner rage, has resigned himself here to a life of domesticity, replete with pet kitten on the floor and a rope tied around his ankles. Patrick Miller says the piece is autobiographical, as if to acknowledge that his former idealism has become firmly grounded. It is a notion that in some ways signals the death of street art's ability to generate new heroes in a time when the hero has once again gone missing, replaced poignantly by a more human uncertainty. In that way, street art may finally be growing up. Meanwhile, the rest of us wait quietly for the return of a dark knight.