A Highway Through History

by Jill Duff-Hoppes

When Robert “Bob” Kahn gazes at a Florida Highwaymen painting, it’s as if the Orlando native is taking a trip down memory lane. Bob and his wife, Flory, have been enthusiastic collectors of this iconic and culturally significant style of landscape art for nearly 20 years.

“The one thing that drew me to it was you see old Florida the way I remember it growing up, going through the back roads with my dad in the early 1950s,” Bob says.

The Florida Highwaymen were a group of African-American artists who began painting landscape scenes of The Sunshine State in the 1950s. The serene imagery they chose to paint often included curved palm trees, sunrises and sunsets in vibrant hues, waves crashing on beaches, lush marshes, water birds, and red poinciana trees.

The artists were fast, prolific workers who shared tips and techniques with each other. They sold their oil paintings – sometimes still wet – at rock-bottom prices, often from the trunks of their cars along old-Florida roadways. The painters, most of whom were from the Fort Pierce area, also traveled from town to town, selling their work to motels, churches, and offices. Because of their unconventional sales methods, the group was eventually dubbed the Florida Highwaymen.

“These paintings intrigued us, and we just started buying up more,” says the 75-year-old Bob. “The paintings are all special and unique. There is a lot of personality there.”

The Kahns amassed their extensive collection in a catch-as-catch-can manner – at auctions, estate sales, and even a few random garage sales.

“Bob would find the paintings here, there, and everywhere,” says Flory, who jokes that the two of them ran out of closet space at one point because they had so much art.

He and Flory have gifted many of these historically significant pieces of art to the Orange County Regional History Center in Orlando. The Kahns are by far the History Center’s biggest donor of Highwaymen art, with more than 60 percent of the museum’s collection having been donated by the Maitland couple.

The Kahns have also gifted 18 important pieces of Highwaymen art to the Smithsonian National Museum of African American History and Culture (NMAAHC) in Washington, D.C. Their donations include works by two of the most well-known members of the group, Alfred Hair and Harold Newton, both now deceased. The Kahns’ contributions are the museum’s only pieces of Highwaymen art.

As major donors to the NMAAHC, the Kahns were invited to a private reception in September 2016, not long before the museum officially opened to the public. The lavish event was attended by the likes of Oprah Winfrey, former First Lady Laura Bush, and the late legendary singer Chuck Berry, who donated a red Cadillac to the museum.

The Kahns made their donations in memory of Bob’s late parents, Wolf and Tybe Kahn. A true Renaissance man, Wolf had many talents and was a skilled artist, himself. In addition, he was an early civil-rights advocate in the community.

For Bob, the personal nostalgia factor of the Highwaymen art isn’t the only reason he’s an avid collector of the work. He also appreciates the entrepreneurial spirit with which the paintings were created.

According to the Smithsonian’s website, the 26 African-American artists who are widely recognized as the original Highwaymen produced about 200,000 paintings from the mid-1950s to 1970. During the era of segregation, the most common jobs available to African Americans in Florida included working on farms and citrus groves or in factories. For these artists, painting was a more appealing and lucrative way to earn a living than manual labor.

At the time, the paintings were sold for as little as $25 apiece, but can now fetch thousands of dollars each. A renewed interest in the artists’ work began in the mid-‘90s, and the Highwaymen were inducted as a group into the Florida Artists Hall of Fame in 2004.

“Here is a group of people who took it upon themselves to better their position, and to increase their earning capacity, and to develop a talent that could be marketed,” says Bob, who has also given Highwaymen paintings to family and friends.

Even after the group’s members went their separate ways, many of the artists continued to paint. Among them was Flory’s favorite of the bunch – Mary Ann Carroll, the only female Highwaymen artist. Mary Ann, who painted as a way of supporting her seven children, died in December 2019.

“She was a tough cookie,” says Flory, who previously worked for The Jewish Pavilion of Central Florida and The Roth Family JCC. “I am totally drawn to her art. I fell in love with her clouds; they’re just beautiful.”

Flory and Bob had the opportunity to chat with the affable Mary Ann in person on several occasions. The artist often made appearances at the Orange County Regional History Center’s twice-a-year Highwaymen art events – which the Kahns helped start. 

“Mary Ann was just a friendly, friendly person, and she would sit and talk to you about whatever you wanted to talk about,” Flory says. “She was very special.”

The Kahns have fond memories of meeting many of the other Highwaymen, as well. Years ago, they took Flory’s young granddaughter, Ella Colley – who was five or six at the time – to a Highwaymen event. While there, Ella drew a picture that all the artists signed, and her family later framed the piece as a cherished memento.

Although Bob is no longer actively searching for Highwaymen art, he wouldn’t pass up an opportunity to snag another piece. But these days, it’s hard to find an authentic early work by one of the original artists.

“If I ran across something, I’d buy it in a heartbeat,” Bob says. “This is Florida history.”