Born in Pelham, Georgia, on March 23, 1932, Roy McLendon moved with his family in 1946 to Delray Beach, Florida, to a small farm where the family earned a living picking beans, a crop they followed as migrant workers. When he was eighteen, he set out on his own and moved to Miami, where he worked as a dishwasher. Considered the second Highwayman, McLendon eventually moved to Gifford, Florida, where he met Harold Newton. Known as the “storyteller” of the group, he is responsible for most of the paintings depicting people. Completely self-taught, McLendon is highly successful and runs a gallery in Fort Pierce with his son, Roy McLendon Jr., who is also an artist.