Bob Thompson's Family Portrait, painted in 1963, represents a bold reimagining of one of Western art's most enduring themes: the Holy Family. The painting showcases Thompson's penchant for transforming classical and Old Master subjects into modern, energetic compositions. Family Portrait subverts traditional representations of the subject through Thompson's distinctive style of flat colors and simplified forms. The central figure—likely Mary—rendered in bold red, dominates the canvas, while Joseph appears as a watchful presence in subdued grey-blue. Thompson's subtle inclusion of the Christ child—represented by just a glimpse of leg beneath Mary's garment—demonstrates his ability to play with viewer expectations and religious symbolism.

A diagonal black wing-like shape traverses the painting, simultaneously foreshadowing Christ's fate and representing a demonic presence common across much of Thompson's output. Indeed, his personal life was often as conflicting and vigorous as his art, as he spent much of his later years struggling with addiction. Bob Thompson completed Family Portrait in New York in 1963, at age 25, just three years before his death.

Born in Louisville, Kentucky in 1937, Thompson emerged as an important voice during the Abstract Expressionism era. Drawing inspiration from Renaissance masters like Nicolas Poussin and Francisco Goya, he developed a distinctive figurative visual language that challenged both artistic and racial conventions. His paintings often transformed historical subjects into dreamlike scenes characterized by flattened forms and rhythms reminiscent of jazz music, an art form he deeply admired.

Despite his tragically short life, he died in Rome at 28, Thompson left an important artistic legacy, and prominent institutions have recognized the significance of Thompson's work. Other examples can be found in, among others, the collections of the Museum of Modern Art, New York, the Smithsonian American Art Museum, Washington, D.C., and the Whitney Museum of American Art, New York, who organized a landmark retrospective exhibition in 1998, solidifying Thompson's place in twentieth-century art.