The Florida Highwaymen movie titled “Legends of the Highway” will debut on DVD and streaming platforms in late 2025, bringing the story of this influential group of Black artists from Fort Pierce and Gifford to a national audience. The film explores the legacy of the Highwaymen, who overcame segregation in 1950s Florida to create and sell vibrant landscape paintings that are now recognized as iconic pieces of state history. The recent passing of renowned Highwaymen artist Al Black has renewed interest in their remarkable contributions.
Florida Highwaymen Movie ‘Legends of the Highway’ Release Dates and Viewing Options
The Florida Highwaymen movie “Legends of the Highway” is set for a two-phase release. According to a news release from the film’s producers, the movie will be available for purchase and rental on DVD and digital platforms starting October 28, 2025. Streaming access will follow on November 25, 2025, on major streaming services, though specific platforms have not been named.
Viewers can rent or buy the film nationwide through Fandango and Prime Video beginning in October. The production company, Triple Hibiscus Productions, has organized several in-person premiere events across Florida, including on the Treasure Coast.
Premiere and Screening Events for Legends of the Highway
- Red Carpet Premiere: October 25 at Cinepolis Jupiter
- Screening: November 8 at Cinepolis Davenport
- Screening and Elliott Museum Event: November 23 at The Lyric Theatre in Stuart
- Screening: December 13 at Cinepolis in Coconut Grove
These events provide opportunities for local audiences to experience the Florida Highwaymen movie before its wide digital release and connect with the legacy of these artists, especially as only four original Highwaymen are still living following recent losses.
What Is the Florida Highwaymen Movie About?
“Legends of the Highway” tells the story of a group of Black artists and a pioneering woman in 1950s Florida. According to the official synopsis, the movie highlights how these artists navigated segregation-era restrictions and built their own path to artistic success. The Highwaymen became known for their vivid landscape paintings, which they sold directly to hotels, offices, and roadside buyers for about $25 each.
The film was shot on location in Atlanta, Georgia, North Carolina, and Florida’s Treasure Coast, according to Kelcie Schwab, vice president of digital for Maverick Entertainment. This regional focus connects the movie to the real places where the Highwaymen lived and worked.
Cast and Creative Team
The Florida Highwaymen movie features an ensemble cast, including:
- Julian Horton (Netflix’s “Beauty in Black”)
- Kelvin Hair (“Respect,” BET’s “Ruthless”)
- Johnell Young (Hulu’s “Wu-Tang: An American Saga”)
- Ashani Roberts (“Sweetwater,” BET’s “Average Joe”)
- Daniel Augustin (Max’s “Rap Sh!t,” HULU’s “How I Met Your Father”)
- John Dixon
- Alec Adams
- Jizzixious Bishop
- Christopher Thomas
Kelvin Hair portrays his grandfather, Alfred Hair, who was one of the original Highwaymen and died in 1970. The film is produced by Triple Hibiscus Productions and distributed by Maverick Entertainment.
Who Were the Florida Highwaymen?
The Florida Highwaymen were a group of 26 Black artists who began painting in the 1950s, primarily in Fort Pierce and Gifford. Under the guidance of Alfred Hair, Harold Newton, and white artist A.E. “Beanie” Backus, they created vivid landscapes that captured Florida’s natural beauty. During the Jim Crow era, Black artists were barred from showing their work in galleries, so the Highwaymen sold their paintings along highways and to local businesses. Their story is intertwined with the broader African American experience in the region, much like the traditions honored during Gullah Geechee heritage celebrations in Fort Pierce.
According to art historians, as many as 200,000 Highwaymen paintings may still exist today. Their works became popular in motels, medical offices, and banks across the state, and the group is now recognized as a significant part of Florida’s cultural history.
Original 26 Highwaymen Artists
- Curtis Arnett
- Hezekiah Baker
- Al Black
- Ellis Buckner
- George Buckner
- Robert Butler
- Mary Ann Carroll
- Johnny Daniels
- Willie Daniels
- Rodney Demps
- James Gibson
- Alfred Hair
- Isaac Knight
- Robert Lewis
- John Maynor
- Roy McLendon
- Alfonso Moran
- Harold Newton
- Lemuel Newton
- Sam Newton
- Willie Reagan
- Livingston Roberts
- Carnell Smith
- Charles Walker
- Sylvester Wells
- Charles Wheeler
Florida Highwaymen Movie Trailer and Public Response
The official trailer for “Legends of the Highway” introduces audiences to the struggles and achievements of the Highwaymen. According to a news release, Gifford native and retired NFL player Kenny Holmes said, “These artists painted their freedom, and their stories deserve to be seen and celebrated.” The film aims to highlight the legacy and cultural impact of the Highwaymen for a new generation.
Frequently Asked Questions About the Florida Highwaymen Movie
What is the Florida Highwaymen movie about?
The Florida Highwaymen movie, “Legends of the Highway,” tells the story of Black artists in 1950s Florida who overcame segregation to create and sell landscape paintings. The film focuses on their journey to artistic recognition and the challenges they faced.
How can I watch the Florida Highwaymen movie?
You can watch the Florida Highwaymen movie on DVD and digital platforms starting October 28, 2025. It will also be available for streaming on major services beginning November 25, 2025, according to the film’s producers.
Are there any in-person screenings of Legends of the Highway?
Yes, several in-person screenings are scheduled in Florida, including events in Jupiter, Davenport, Stuart, and Coconut Grove. These events occur before the national streaming release.
Where were the Florida Highwaymen from?
The original Florida Highwaymen artists lived and worked mainly in Fort Pierce and Gifford, Florida. Their paintings often feature the landscapes and natural beauty of the region.
Can you still buy Florida Highwaymen paintings today?
Yes, original and reproduction Florida Highwaymen paintings are still available through art dealers, auctions, and some galleries. Their work remains highly valued by collectors and art enthusiasts.
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