Portraits form a thread throughout Indiana’s work, from the self-portraits of his art school years to his powerful Mother and Father (1963–1966). Indiana is most known, however, for the symbolic portraits he began painting in the early 1960s. In these he employs significant colors, shapes, numbers and words to create homages to artists and literary figures such as Charles Demuth and Herman Melville, as well as portraits of family members and friends.
Red Sails is a symbolic portrait that commemorates the artist’s father, Earl Clark. Indiana began the painting after hearing a vagrant in Jeanette Park sing “Red Sails in the Sunset.” The incident brought back the memory of his father playing the song on the piano, upon which the song’s sheet music was kept. Yet while the painting was inspired by a memory of his father, it also illustrates the many layers of meaning that are characteristic of Indiana’s work. The artist frequently incorporates personal references into his works, and Red Sails recalls not only his father but the ships and daily life the artist knew from living on the Coenties Slip waterfront. Furthermore, Indiana identifies himself strongly as an American painter, and the red, white and blue color scheme can be read as an allusion to the American flag.