If great art tends to come with ambiguities, then, of course, great artists have the same tendency. The life and work of Archibald Motley was full of them. He grappled with the issues of the day in a profoundly honest way, painting complex topics without oversimplifying or telling the viewer exactly how to feel. Because of this, and the inherent complexities of his life, he is an especially slippery artist to capture.

Although his name is associated with other leading figures of the Harlem Renaissance—such as Langston Hughes, Duke Ellington, and Romare Bearden—Motley never lived in New York City. The mixed-race, African American artist instead provides us with a view of black culture in Chicago in the 1920s and 1930s; this, like so many black histories, is severely underrepresented in prominent American museums. That his work continually appears in the most hallowed museums is remarkable, yet easy to understand: he never stopped giving the critics something to grapple with.

Subverting stereotypes

As a young boy, Motley’s family moved to Chicago from Louisiana. There he would attend college at the prestigious School at the Art Institute of Chicago, learning traditional painting techniques as well as 1920s-specific painting theories. These incorporated phrenology and physiognomy, both popular pseudosciences that use visual cues from the face and head to predict mental characteristics. He combined these two painting systems to create a visual language of black representation that was radical and did not yet exist in the art world: portrait paintings of black people that granted subjects the same dignity and attention that portrait painting had always granted white people. Motley would use subtle language to indicate his sitters’ intelligence and refinement, like slightly squinted eyes and long, elegant fingers.

After graduating from SAIC, he received a Guggenheim Fellowship, in 1929. This allowed him to study in Paris, where he would continue to learn how to emulate European portraiture. He became particularly enamored by Eugène Delacroix, Rembrandt van Rijn, and Frans Hals. In 1928, Motley became the first black artist to have a solo show in New York City, where he sold 22 out of the 26 exhibited paintings.

His portrait paintings used the visual language of white European portraiture to subvert black stereotypes. By bringing out individual characteristics with particular attention to the uniqueness of skin tone, he demonstrated that there was no monolithic black identity. These was irreverent, revolutionary, and masterful—but they were just the first half of Motley’s artistic evolution.

A new style brings new complications

In the 1930s, Motley took a turn, complicating his own legacy by breaking out of portraiture and into a totally original style of painting. These works—capturing the black experience in Chicago’s “Black Belt” neighborhood—have come to define Motley today. They are identifiable by canvases filled with singing and dancing in the middle of the street; by their compressed space, bringing its many subjects elbow to elbow; by their saturated color, evoking liveliness and happiness; and by their repeated shapes, paired with various light sources—both artificial and natural—that simultaneously reflect jazz music’s composed rhythm and spontaneity.

If this era brought more visual originality than his portrait period, it also came with ambiguities some scholars still don’t know what to do with. Some have even contended that they contain representations of racist stereotypes. In his paintings Carnival (1937) and Gettin’ Religion (1948), for example, central figures are portrayed with the comically large, red lips characteristic of blackface minstrelsy that purposefully homogenized black people as lazy buffoons, stripping them of the kind of dignity Motley sought to instill.

Many art historians read these Motley figures optimistically, pointing out that Motley’s inclusion of these characters among a sea of black figures with diverse skin tones, dress styles, body shapes, ethnicities, religions, and personalities speaks to the wide range of possible “definitions” of blackness, and that Motley ultimately argues (as he always has) that there is no such thing as a definition of blackness. Motley’s scenes of black communities show a world where whiteness, and white racist portrayals of black people, are irrelevant—where a man with large red lips doesn’t read as a racist caricature, but as much as a complex individual as a light-skinned woman, a tall man, or a bald loner.

Not all of Motley’s scenes of Chicago feature an all-black cast. In fact, most have a slew of characters with unclear ethnic or racial backgrounds. Others place one or two conspicuous black figures amongst many white people, like in Barbeque (1960), or, like in Street Scene, Chicago (1936), a white nefarious police officer amongst a diverse crowd distracted by their lively corner.

Whatever the Motley painting, close looking and deep thinking will always reveal a variety of questions that lead to complex considerations of race, community, and representation. It’s hard to imagine his work becoming less relevant in a world that still struggles with race. The opposite in fact—as we become ever more accustomed to asking hard questions, it’s easier to turn to those Motley asked some 80 years ago.