Livingston Roberts was there at the start of the Highwaymen’s enterprise, befriending Alfred Hair in 1961 just as Hair was embarking on his remarkable career. They became close friends, working together and exchanging artistic ideas. Hair’s fast painting and Newton’s refined naturalism set the parameters of the Highwaymen style, while Roberts, McLendon, and James Gibson, were the first to join the ranks of the group and add their own artistic interpretations of the Florida landscape. The success of Highwaymen art depended on a stripped-bare aesthetic, and Roberts’s paintings were particularly unembellished. This is not to suggest that they were inferior paintings; to the contrary, he accomplished more with less.