Livingston “Castro” Roberts was known for his meticulous detail, emotive rendering of colorful skies, and intense reflective bodies of water. He began painting at a young age, using leftover house paint to create his earliest works. As a seasoned artist, Roberts served as a mentor and teacher to younger members of the Florida Highwaymen. Of the twenty-six Highwaymen artists, Roberts is among the nine artists are considered the founders of the group that became famous for selling landscape canvases out of car trunks in the early 1950s when segregation laws prevented African Americans from selling in galleries.