About the HighwaymenNote: The following information is derived primarily from Gary Monroe's original researchThe Highwaymen is the name given to a group of twenty-six African
American artists from Fort Pierce, Florida who, beginning in the 1950s,
painted Florida landscape paintings and sold them out of their cars,
traveling across the local highways in search of new customers.

In early 1950s Florida, the options were limited for young
African-Americans trying to figure out how to make a living. Many
worked in citrus groves or packing houses for extremely low daily
wages. Harold Newton and Alfred Hair had both been given instruction by
the then well-established Florida landscape painter A.E. Backus, and
they were interested in the idea of making a living by selling their
artwork.
But galleries were not willing to sell art from
self-taught African Americans. So they began mass-producing their
paintings, piling them into their cars, and selling them door-to-door
to offices, restaurants, motels, and anyone else interested in buying a
Florida landscape painting for the low price of $25 each. They painted
in their garages on inexpensive Upson board or masonite, framed the
paintings with crown molding, painted the frame gold for an "antique"
look, and soon began recruiting friends and family to help with
production and sales. At times, paintings were being produced so fast
that they would be sold before the paint had dried.
The Highwaymen, while heavily influenced by A.E. Backus, nonetheless
created their own style of Florida landscape painting. They used bright
and vivid colors to depict such Florida icons as windswept beaches,
still lagoons, brilliant sunsets, and lone palm trees. In focusing on
speed of production, they inadvertently created a style that was
significantly less self-conscious than most mainstream art of the time.
From the 1950s through the 1980s, they are estimated to have produced
somewhere between 50,000 and 200,000 paintings.
More a loose
association of friends than a formal group, they did not become known
as "The Highwaymen" until the moniker was given to them in a 1995
article written by Florida art collector and museum curator Jim Fitch.
During the 1990s, interest in "Outsider Art" was growing, and soon an
article in The New York Times was applauding the rediscovery of The
Highwaymen paintings, causing their value to skyrocket. Today, the
paintings are highly sought after by collectors.
In
2004, the twenty-six Highwaymen artists were inducted into the Florida
Artists Hall of Fame. Of these twenty-six artists, nine are considered
original Highwaymen. The Gray Brewer Highwaymen Collection features
paintings by six of these original Highwaymen: Harold Newton, Alfred
Hair, James Gibson, Livingston Roberts, Roy McLendon, and Sam Newton.