Although most Highwaymen paintings are devoid of people, Roy McLendon sometimes added figures as points of interest in his landscapes. This indicates a skillset that few of the artists developed. Indeed McLendon painted with more patience than most of the others, and his paintings were realized in a manner consistent with Backus’s and Newton’s art.

McLendon dropped out of school around the ninth grade, and as a young man did a variety of jobs, including migrant labor, to support himself and his growing family. Although McLendon painted since childhood, seeing Newton at work in his backyard studio and Alfred Hair market paintings with aplomb encouraged him to focus on his painting. Given his ability, he successfully became a fulltime artist and is recognized as one of the central Highwaymen artists.