Wiley is the more famous of the two, especially for his large-format, meticulously designed images of contemporary African-American men rendered in the heroic stance and sometimes the trappings of older painting styles. He has posed young men dressed in hip-hop style into detailed and richly colored backgrounds reminiscent of Dutch masters, or painters such as Velázquez, Holbein, Manet and Titian. He has painted an equestrian portrait of Michael Jackson, and worked with stained glass to create modern takes on a rich tradition of Christian imagery. His work, which is produced by a large studio of painters, is highly sought after, widely collected and frequently exhibited, including at a solo exhibition at the Virginia Museum of Fine Arts last year.
More surprising, and more likely to make waves in the art world, is the choice of Sherald to paint Mrs. Obama’s portrait. Sherald, a Baltimore-based artist, won the $25,000 2016 Outwin Boochever Portrait Competition, hosted by the National Portrait Gallery, last year. The triennial competition helped bring Sherald’s work to a larger audience, and Sherald’s winning work, “Miss Everything (Unsuppressed Deliverance),” dominated an exhibition of finalists and other winners. The painting, a rich study in skin tones and textures against a sumptuous blue background, depicted an elegant woman holding a giant tea cup and saucer, with a jaunty red hat pulled down on one side of her face.
The selection of both artists feels eminently well-considered, just like the choice of Tod Williams Billie Tsien architects to design the Obama library on the south side of Chicago (initial plans were unveiled last May). There’s little doubt that the artists, like the architects, have the visual chops to do the job. And yet both artists have earned (or are earning) plaudits from audiences who expect contemporary artists to bring something distinctively contemporary and original to their work. If there’s a safe center to the cutting edge, the Obamas seem sure to find it. Like the Obamas’ personal presentation, the paintings are almost sure to look a lot tailored and just a little trendy, without crossing any lines that might discomfit popular expectations.
The portraits will join a gallery of presidential imagery that becomes increasingly edgy beginning with Elaine de Kooning’s 1963 portrait of John F. Kennedy. For much of the history of presidential portraiture, the predominant style was essentially consistent and continuous with historic styles dating back to the 18th century. Only with the brightly colored and almost sketchy image of Kennedy do the artists chosen by the Gallery take more liberties and assert a painterly agenda equal or greater to the image as an icon of power and prestige. The choice of Wiley will introduce an interesting twist to this dynamic: Wiley has never clearly resolved the ambiguity and irony around his use of historical styles. Is he deflating their received power? Or elevating the perceived status of his subjects by rendering them in the historical fancy dress of classic portraiture? And how will he deal with a subject who was, for eight years, the most powerful man in the world, wielding a global influence far in excess of any of the kings or emperors whose portraits so deeply inform Wiley’s own interest in the form? If the essence of Wiley’s work is a possible dissonance between the subject and the style, how will he paint a man who wore the trappings of power with total comfort and without any sense of dissonance at all?
The portraits are still in the works and will be unveiled early next year. The National Portrait Gallery began commissioning presidential portraits to supplement its collection of historic presidential imagery with a painting of George H.W. Bush. The White House also creates and maintains a presidential portrait collection.