Charles Sebree had many talents; in addition to being a painter, he was also a dancer, designed sets and costumes, and wrote plays. Along the way he served in the United States Navy during World War II.

Sebree’s birthplace is variously listed as White City, a mining community, or nearby Madisonville, Kentucky, in the south central part of the state. In 1924, at age ten, he and his mother joined the northern migration and settled in Chicago, Illinois. An early interest in art was nurtured by an uncle who painted and drew cartoons. Sebree attended Burke Elementary School on the south side of Chicago. When he was fourteen the Chicago Renaissance Society, an organization founded by university professors who sought to nurture art, purchased Sebree’s drawing Seated Boy  for twenty-five dollars and awarded him a scholarship for Saturday classes at the Art Institute. Although he was living pretty much on his own from the time he was fourteen, he graduated in 1932 from Englewood High School, the alma mater of such notable artists as Archibald Motley, Eldzier Cortor, and Margaret Burroughs.

In 1934 Sebree met with considerable success at the Grant Park Outdoor Art Fair, selling everything he took to the fair for display.  His art caused significant interest among other artists while making an impact on visitors. Sebree appeared to possess a peculiar talent for producing work with an emotional quality which seemed strange to artists with academic training. He enrolled at the Institute of Design, also known as the “New Bauhaus,” and which later became part of the Illinois Institute of Technology. During the 1930s Sebree danced and designed sets for a local dance company, and between 1936 and 1938 he participated in the easel division of the Illinois Art Project, a sub-project of the Federal Art Project of the Works Progress Administration. 

Sebree was befriended by noted gallerist and advocate for modernist art, Katherine Kuh. She recounted how he “regularly stole hundreds of postage stamps from the gallery and then resold them. When I confronted him with the problem, he said it would be ‘dishonest’ for him to pretend his behavior might change. ‘After all,’ he reminded me ‘we are good friends.’ And believe it or not, he continued to steal, though of course, honestly, and I continued to show his work.” He was the only African American represented by her, and in one exhibition his art was shown alongside that of Pablo Picasso, Henri Matisse, and Amedeo Modigliani. Perhaps through Kuh, Sebree came to know the work of other European masters Georges Rouault and Paul Klee, whose paintings clearly influenced him: the former’s use of black lines and half-length figures close to the picture plane are parallel to Sebree’s, and the latter’s feeling of innocence also imbues much of Sebree’s output. His circle included Gertrude Abercrombie, a painter with a surrealist bent, who entertained in her home such figures as the musicians Dizzy Gillespie and Charlie Parker, as well as the playwright Thornton Wilder and Alain Locke, a philosopher associated with Howard University in Washington, DC.

In 1942 Sebree was drafted and was stationed at Camp Robert Smalls, a segregated unit of Naval Station Great Lakes base north of Chicago. While there he and an associate produced a pair of plays, one of which, The Ballad of Dorrie Miller, told the story of the black naval mess attendant who rescued several sailors after the bombing of Pearl Harbor. After the war Sebree moved to New York, and was awarded a Rosenwald Fellowship in 1945. Two years later he moved to Washington, DC, to work on set designs and costumes for a production at Howard University. He continued to paint, usually on a small scale because he worked at his kitchen table; he often used casein on textured paper. By the mid-1950s his energy was focused more on the theater culminating in an off-Broadway production of Mrs. Patterson, starring Eartha Kitt in a somewhat autobiographical story about a teenage girl in a small town in Kentucky who suffered from boredom and dreamed of a new life in Chicago.

Although Sebree found himself attached to particular groups and places, he had a vagabond streak and moved regularly and often in a rush. His lifestyle may explain his predisposition to his subjects, often captured in small formats, and reminiscent of a nomadic life.