Highball on the Redball Manifest is one of a group of symbolic family portraits, along with Red Sails (1963), which commemorates the artist’s father, and Parrot (1967), which commemorates an uncle. The painting is a portrait of Indiana’s paternal grandfather, who was a locomotive driver on the Pennsylvania Railroad. In his artist statement on the work, Indiana explained that the term “Highball on the Redball Manifest” was an old American railroading term for the signal “All-Clear for a fast express.”
The artist also linked the painting to another family portrait, Mother and Father (1963–66), by noting that the grays in both works came from the same paint jars. Indiana frequently inserted personal references into his work; here he does so through the number “25,” which was the address of his second studio on Coenties Slip.