Alfred Hair is the progenitor of the Highwaymen. His goal was not to form a school of art or an art movement, but that is what happened. He simply wanted an alternative source of income to the menial labor that seemed likely for young African Americans growing up in the shadow of Jim Crow. Through his spirit of generosity, Hair offered friends a means to beat the odds by learning to paint the Florida landscape. Furthermore, he showed them how to market these paintings along the state’s eastern seaboard. He gave the group a semblance of form, but for the Highwaymen there were no rules or dues, just opportunities and ambition.

Zanobia Jefferson, Hair’s high school art teacher in Fort Pierce, Florida, recognized his talent and encouraged him to pursue his interest in art. In the later 1950s she introduced him to the celebrated Florida landscape painter Albert E. Backus. During his high school years, Hair took lessons from Backus, and eventually the two became friends.

Alfred Hair’s work was directly inspired by Backus; however, Hair determined that as an African American artist he could not attain the same level of success as his white mentor unless he sold scores of paintings at much lower prices. To that end Hair developed a unique style of fast painting that allowed him to complete 20 paintings a day. To facilitate his production, he hired friends and neighbors to prepare boards, build frames, and go on the road to sell paintings. His paintings sold very well, and his success inspired others in the community to try their hand at painting. Tragically, in 1970 Hair was murdered by an acquaintance in a local Highwaymen hangout called Eddie’s Place. His loss was a shock to the community and the cohort of artists. A decade later their enterprise came to a near halt.