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From Shepard Fairey to Kehinde Wiley, Pop Art Brought Obama to Life

Unveiled Monday in a ceremony at the National Portrait Gallery, the official paintings of the former president and first lady—by Wiley and Amy Sherald, respectively—celebrate a political duo enshrined in pop symbolism

Getty Images/Ringer illustration

In 2008, the Obama campaign didn’t design or commission its most famous memorabilia — a poster featuring Obama’s face jutting over a one-word, says-it-all slogan, “HOPE.”

District Renaissance Photo by David S. Holloway/Getty Images

Based on an April 2006 photo that Mannie Garcia took for the Associated Press, the American street artist Shepard Fairey’s image transformed a boring head shot of the youthful Democratic challenger Barack Obama into a colorful splash of campaign propaganda. Fairey rendered Obama’s portrait red, white, and blue, and he applied the “PROGRESS” legend (and later, the more famous “HOPE”) as an urgent response to the disastrous and demoralizing Bush years. As a meme, the image proliferated through all digital and physical pores of American political life. Sometimes you’d see it as a light-pole sticker. Other times you’d see it as a friend’s Facebook profile photo. I worked in Iowa, New Hampshire, and Washington, D.C., as a young Obama intern; naturally, I saw the image everywhere. In fact, the image spread globally, morphing to suit countless subjects of celebration and satire. The Obama “HOPE” poster was hip and inspirational. Now, it’s iconic — the crown jewel in a treasure trove of Obama pop iconography. The “HOPE” poster represents not only a euphoric spike in American optimism; it also encapsulates the very nature of Obama’s political career: a rush of pop fluency and empathy, deployed toward ends more complicated and distressing than the slogan lets on.

On Monday, the portrait artists Kehinde Wiley and Amy Sherald debuted their respective portraits of Barack and Michelle Obama at the National Portrait Gallery in D.C. Wiley is the more famous artist, and he has distinguished himself among mainstream audiences by painting extravagant portraits of black subjects, including entertainers, athletes, and “street-cast” subjects from cities all across the world. For more than a decade now, the National Portrait Gallery has hosted Wiley’s portraits of black American royalty, including LL Cool J, Ice-T, and Big Daddy Kane. Sherald, too, paints striking portraits of black subjects, most of them common folk styled in a come-as-you-are fashion, but with the boldest possible hues against blanched skin. Sherald dramatizes all walks of American life.

Admirably, Wiley didn’t temper his boldest signatures in his portrait of Barack Obama; and Sherald put only a modest damper on her style by flooding Michelle Obama’s dress with neutralizing black and white. If you flip through the catalog of this country’s official presidential portraits, you will notice how wildly Wiley and Sherald’s contributions stick out. Wiley and Sherald are the first black artists whom the museum has ever commissioned (at the first family’s choosing) for presidential portraits, and they have produced two wonderfully unconventional depictions of the first black president and the first black first lady. Barack Obama sits forward with his arms crossed upon his knees, a wall of greenery and flowers at his back. Michelle Obama sits in a floating, pointed pose, her skin pencil-gray against a broad blue background, and red, pink, and yellow accents in her otherwise black-and-white dress. The former president and first lady accompanied Wiley and Sherald on stage in the gallery’s main courtyard, offering brief praise of both portraits; Barack Obama commended Sherald for “capturing the hotness of the woman I love.”

The portraits are so unconventional as to seem designed to shock and irritate at least some viewers like no official presidential portrait has before. As the unveiling ceremony streamed live from the National Portrait Gallery, social media unraveled into passive-aggressively warring fits of praise and snark, optimism and skepticism — the most impressive tweets fashioning both moods in tandem — with assessments of the art largely determined by one’s overall esteem for Barack Obama. Additionally, the enthusiasm for Wiley’s pop art commemoration of Obama’s presidency raises the frustrating question of whether Obama’s legacy, and his inherent racial significance, will always trump any broad and meaningful reckoning with the president’s legacy outside of Obamacare. As far as these portraits are concerned, the immediate state of that tension is quite clear. The Obamas departed the White House 13 months ago, and yet it seems that only now are we seeing the last definitive works of Obama memorabilia. The Wiley and Sherald portraits are “HOPE,” revisited.

These portraits exist for posterity’s sake, so let’s consider them accordingly: If you’re a school-aged child scanning the historical record for clues to the great shifts in political culture, you’d likely find it strange that the long procession of muddy, naturalistic presidential portraits is suddenly punctuated by a painting of a black man, the first black man to occupy that role, poised at the edge of his seat, deep in the leaves, awash in unprecedented color. There sits a U.S. president whose very presence disrupts the flow of history on some profound aesthetic level. Investigating further, you would learn that this man spent his two presidential terms blending into the cruel machinery of American power and yet also sticking out awkwardly from his destined setting. The president’s wife, Michelle, an attorney, appears no more or less conventionally than Barack. Together, they form two halves of a joint statement, and yet she is styled distinctly: an independent woman who requires no caption for you to read the accomplishment in her face. The hope is very much alive in these portraits, though it’s faded drastically from the faces of Obama’s supporters given the many compromises, shortcomings, and political disasters that such exuberant images can never depict in focus.