Oct 23, 2023 - News

Florida Highwaymen legacy continues with exhibit at St. Pete museum

A man in a brow button down, pants and newspaper boy cap leaning on a blue-green vintage car. Several framed paintings of Florida landscapes lean against the car. A royal poinciana tree blooms red flowers in the background.

McLendon also enjoys collecting hot rod cars. Photo: Courtesy of Ray McLendon

Ray McLendon likes painting reflections best. He can play with them, blurring the lines and colors of a luminescent moon shining down on a bay, or a deep-orange sunset bleeding onto a lagoon.

  • The scenes are where his background as an abstract artist shines through an iconic landscape style made famous, in part, by his father.

The intrigue: McLendon's father, Roy, is one of the 26 Black artists known as the Florida Highwaymen, who sold their vivid landscape paintings out of their cars during the segregated 1950s and 60s.

  • Ray, 67, is part of the second generation carrying on their legacy.

Driving the news: His art is on display at the Woodson African American Museum of Florida in St. Petersburg as part of an exhibition called "Florida Highwaymen: The Next Generation – The Legacy Continues."

  • It's free and runs through mid-December, and McLendon will hold a meet-and-greet on Nov. 11 during the museum's monthly art walk.

Why it matters: The exhibition shows how a unique piece of Florida's Black history is continuing on today.

  • It also includes a handful of pieces by a burgeoning third generation, two of Ray's sons, one of whom lives here in Tampa.

State of play: The original artists β€” 25 men and one woman β€” were largely self-taught, although one of the first Highwaymen, Alfred Hair, honed his craft under the direction of A. E. Backus, a renowned white landscape artist from Fort Pierce who went on to mentor several more in the group.

Two paintings, one of an orange-yellow sunset over a lagoon, the other of a bridge looking onto green water.
A sampling of the paintings on display at the Woodson. Photo: Kathryn Varn/Axios

Catch up quick: With segregation shutting the Highwaymen out of gallery spaces, they took to the road, driving up and down Florida's Atlantic coast selling their art as decor for businesses and homes for around $25 to $35 a pop, equivalent to about $400 today.

Between the lines: Ray didn't always want to continue his father's legacy. He worked as a social worker then as the owner of a crab shack in Fort Pierce. He sold his abstract paintings on the side for extra money.

  • But at a Highwaymen-themed art show a couple decades ago, Ray and his father saw a painting of two palm trees that "just wasn't right," he told Axios, recalling the proportions were out of whack.
  • Roy bet his son the painting would still sell. Ray didn't believe him but was soon proven wrong. Much like the older generation, he saw the opportunity to make good money off the paintings.

The latest: Ray has been a full-time artist for nine years now and owns a gallery in Vero Beach. His father, now in his 90s, is one of the last living original Highwaymen and still does work on commission, his son said.

What he's saying: "I like people to understand, no matter where you come from, you can become great at what you do," Ray told Axios. "It's not where you come from. It's where you're going."


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