Lecture: An Overview of the Florida Highwaymen

Park Ave Magazine | Winter Park Florida

An Overview of the Florida Highwaymen…from their humble beginnings to their art’s cultural phenomenon. Presented by Gary Monroe

About The Exhibit

Gary Monroe has received grants from the National Endowment for the Arts, Florida Department of State’s Division of Cultural Affairs, Florida Humanities Council, and the Fulbright Foundation to support his photography and writing. With a focus on “Outsider” and vernacular art, Mr. Monroe, the leading authority on the Highwaymen, has authored several books about the artists. He tells a story that relates their rising above racial attitudes, the nostalgia for unspoiled Florida, and the creative spirit of the original 26 painters.

Theirs is a story of entrepreneurs who sought not to settle for the meager existence offered by the agricultural and citrus industries.

This is a common vocation for many African-American workers in Florida at the time. Art to the Highwaymen was a craft, a way to earn a living. At the time, galleries weren’t showing the work of unknown, self-taught African-American artists. Instead, the Highwaymen painted from their garages and backyards on inexpensive Upson board, framed their work with carpenter’s trim, then traveled Florida’s east coast to sell their still-wet paintings “from door to door,” at hotels, offices, businesses, and residences.

The Highwaymen


Gary Monroe brings an artist’s sensibility to looking at the paintings.  He contextualizes the Highwaymen’s art in the Jim Crow South during Florida’s optimistic space-age years. He discusses the Sunshine State as a place to reinvent one’s self during the postwar boom. This lecture explains how these paintings complimented this American dream sentiment. The Highwaymen’s technique allowed them to produce brilliantly colored landscape paintings quickly and effectively. It is estimated that they created some 200,000 of their original paintings.

The Florida Artists Hall of Fame inducted The Highwaymen in 2004. Based on Mr. Monroe’s nomination. He facilitated National Public Radio when they produced their Highwaymen series. He has delivered some 300 public lectures and written many articles about the Highwaymen, and curates museum exhibitions of Highwaymen art.