Livingston Roberts

Highwaymen Artist

Livingston “Castro” Roberts

Livingston Roberts, known as “Castro” to his friends for his Fidel Castro-like beard, was one of the earliest Florida Highwaymen painters to join artists Alfred Hair and Harold Newton in painting and selling their works along Florida’s highways.  

Born January 21, 1942, in Elkton, Fla., Roberts was the second oldest in a family of 12 children and a lover of Florida’s landscapes from a young age. When he was around 15, The Highwaymen Trail, a heritage trail organization run by the city of Fort Pierce and the Florida Humanities Councilreports, Roberts told his mother he could reproduce a painting the family had hanging in their home and she encouraged him to do so. After a hunt for left over house paint and supplies, the budding young artist set to work and, according to The Highwaymen Trail, “By all accounts it was an impressive first effort at creating a painting. A cousin later asked him to create more paintings for his home in Hallandale, Florida.”

Painting quickly became a mainstay in the teenage Roberts’ life and, after moving to Fort Pierce in to live with his grandmother, he met Alfred Hair and, bonding over their shared love of painting, the two young artists became fast friends. Roberts became close with well-known Florida landscape painter A.E. “Bean” Backus, a white artist who served as mentor to many of the Highwaymen – and formal teacher to Alfred Hair – and learned by spending time at Backus’ studio and watching him work. When Hair began producing paintings and taking them out on the road to sell door to door, Roberts was the first artist to join him.  

In their earliest days, Roberts’ brother Ernest would take his work out on the road to sell door to door, but Roberts himself was often the salesmen of his pieces. “Mona Mills Walker, a secretary and bookkeeper in a Sanford medical office, remembered that in the early Highwaymen days, Livingston Roberts would come into her office a few times a year,” The Highwaymen Trail reports. “He would line up about six paintings in their hallway for the entire staff to look and buy.”

As business boomed, and Hair brought salesmen like Al Black into the enterprise they began selling the artists’ work out on the road, freeing the painters to focus on producing paintings. “He was the best painter of all the Highwaymen, and the nicest,” Al Black told The Highwaymen Trail in an interview. “I have sold Castro’s paintings since 1963. From Key West to Montgomery, Alabama, you just show them and his paintings sell themselves.”

Livingston Roberts was also a beloved teacher and mentor to many of the Highwaymen artists who joined the group and sought to improve their painting. “Whenever I needed inspiration, I would go over to Castro’s backyard to watch him paint,” Highwaymen artist James Gibson said when he spoke at Robert’s memorial after his death in 2004. “He was a charismatic teacher as much as an artist,” Roberts’ sister Gertrude recalled. “His backyard was a gathering place for his fellow Highwaymen as well as people of all ages who came by to watch him paint. He had a great sense of humor and enjoyed telling stories, having a beer, a cigarette, and a good laugh. If anyone needed money and he had it to give, it was readily handed over.”   

After Alfred Hair’s murder in 1970, Roberts left Florida for a few years, needing some time away to heal from the loss of such a close friend. He eventually returned to Fort Pierce and to his painting and remained a driven and consistent painter for 47 years, until the end of his life. His work is known for its meticulous detail and Roberts emotive rendering of colorful skies and intensely reflective waterways. 

Inducted into the Florida Artists Hall of Fame in 2004, Livingston Roberts is considered today one of the most influential and accomplished of the Highwaymen artists, and his work hangs in numerous significant collections throughout the country.

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