The Highwaymen: A Roadside Renaissance

A roadside stop for boiled peanuts or local produce is typical for anyone who frequents rural Southern roads. It’s far less common to find fine art being sold out of the back of a pickup truck - that is, unless you’re living in Fort Pierce, Florida in the 1950s and 60s.

The story goes that a high school student and aspiring creative, Alfred Hair, met artist A.E. "Bean" Backus who offered to train him in painting. Armed with new techniques, Hair quickly excelled at his craft, painting vibrant Florida scenes that would stun any collector. Others in the community saw what Hair could do and asked if they could learn too. This sparked a movement for other young men (and at least one woman) who saw an opportunity for creative expression and financial independence. Hair shared his techniques with anyone who wanted to learn, and before long there were twenty-six African-American landscape artists, who would later become known as the Highwaymen.

Hair’s home became an artist hangout and a virtual art factory for the group. The techniques that Hair developed and taught enabled the painters to work quickly and skillfully. Motivated to paint their way to a better life, the Highwaymen produced incredible artwork at a rapid pace.

Galleries weren’t open to African-American art during a time when most of the South was still segregated, but the group didn’t let that stop them. They sold paintings out of their cars and went door-to-door to businesses, selling their work for $25 per painting! It’s estimated that more than 200,000 paintings were produced by the Highwaymen from the 1950s-70s.

Decades later, a prominent art collector raved about the “Florida Highwaymen” and the New York Times picked up the story. Now their paintings are worth anywhere from $500-$45,000. You can even tour The Highwaymen Heritage Trail and see where these inspiring artists honed their craft.

The determination and talent of the Highwaymen is incredible. Rumors are that some were able to paint up to 30 paintings a day! It makes me wonder if my parents ever missed a chance to snag a $25 masterpiece on the way home from a summer vacation…