Art / Paintings

Billy Yeager is the only person known to have painted alongside the famous folk artists known as The Florida Highwaymen.

In 2000 he produced a documentary film about his experience.

Yeager was taught how to paint Florida Landscape paintings on masonite boards by one of the original Florida Highwaymen Livingston Roberts, also known as “Castro,” who was inducted into the Florida Artists Hall of Fame in 2004.

Yeager’s Original.

Yeager and Castro with the only painting ever created by an Official Highwaymen and an outsider.

Billy has painted only about 12 paintings, and this has made them highly collectable.

billy blue days

Blue Daze.

Some of these paintings were featured on the covers of some of Billy’s handmade CDs.

Green Day.

On the documentary The Highwaymen The Other Side of the Road,

Yeager discovers where the Highwaymen gather to paint, and captures rare moments with artists Charles Walker, Johnny Daniels, Jimmy Stovall, and Livingston Roberts all gathered together talking about the old days, Alfred Hair, Al Black, and the lost Freddie paintings.

Yeager interviews Alfred Hair’s family and others who knew Alfred personally.

Yeager with Charles Walker and Livingston Roberts in Ft. Pierce, FL.

Yeager also finds Jimmy Stovall, who once painted with the 5 original Highwaymen when he was only 16 years old, and stages a reunion with Livingston Roberts in his backyard. (They hadn’t seen each other in 25 years.)

Livingston states on camera, “There’s a real Highwaymen, he was here from the beginning.”


With Charles Walker.

Rodney Demps.

With Manny and Johnny Daniels.

Jimmy Stovall with Alfred Hair’s very first painting on canvas.

Charles Walker painting in the backyard of Livingston Roberts.

With Hezekiah Baker and Al Black.

With Albert Black at Tomoka State Prison.

The Highwaymen

were mostly self-taught painters who painted on inexpensive Upson board.

The name refers to African American artists, mostly from the Fort Pierce area, who painted landscapes and made a living selling them, door to door, to businesses and individuals throughout the state from the mid-1950s through the 1980s. They also were peddled from the trunks of their cars.

Today their 100,000 plus paintings have gathered significant interest and have become quite collectible. At auctions these particular painters works have been recognized with high prices. In recent years there has been many forged paintings sold on eBay and at many galleries. Because there are over 26 artists and they signed their names scratched with a nail into the paintings that were still wet makes it easy to purchase similar Florida scene paintings and forge the artists names who only knew how to print.

Livingston Roberts showed Yeager, not only how to paint, but how to recognize authentic Florida Highwaymen Paintings.

In 2002 Yeager was featured on FOX NEWS.