Gertrude Ambercrombie once stated, “Surrealism is meant for me because I am a pretty realistic person but I don’t like all I see. So I dream that it is changed. Then I change it to the way I want it.” In the pre-Civil Rights era there was a lot about reality not to like, and it took great vision to move beyond the status quo and sketch out new possibilities. Ambercrombie not only reshaped reality through her paintings but lived a life in which she could manifest her personal ideals. A white artist, Ambercrombie moved beyond color barriers to build community. The painter was close friends with Charlie Parker, Sarah Vaughan, and Dizzy Gillespie, the latter of whom once said, “Her paintings were jazz.” Ambercrombie drew great inspiration from her friendship with these musicians who embodied bold, new possibilities. Although the painting Figure Facing East might have been drawn from a melancholic moment in Ambercrombie’s own life, not unlike the musicians she was so fond of, she spun her sorrow into a dream space where moonlight and shadows set the scene for star-kissed serenades.