The Florida Highwaymen (2003)

Billy Yeager purchases an oil painting and discovers that it is done by one of the artists known as the Florida Highwaymen. Yeager travels to the artist's hometown in Fort Pierce, Florida, where as many as 23 Highwaymen artists have been known to have gathered from the 1960s to paint Florida landscapes and sell their paintings as a way to earn an income and escape from the hard labor of picking oranges. Yeager infiltrates into their artistic community after driving from Lake Worth, Florida, to Ft. Pierce for over a year. He gains their trust, even being allowed to meet with one of the original artists, Albert Black, who is incarcerated at the Tomoka State Prison. During the interview, Al Black gives Billy a hand-drawn map that includes a message to give to another Florida Highwaymen artist and close friend, Livingston Roberts, also known as "Castro." The map reveals the location of a dilapidated house where Al Black stashed 100s of paintings from the 1960s, which he never sold. Together Castor and Billy travel to find the house where the paintings are located that could be worth 100s of thousands of dollars.