After beginning in printmaking, specifically woodcuts and lithographs, he made the shift to painting with Still Life with Postage Stamp in 1955.
Realism as a reaction against Abstract Expressionism gained a significant following starting in the late 1960s, the most visible of the movement being the photorealists and the super-realists, artists such as Richard Estes and Chuck Close.
While Billy Morrow Jackson was certainly painting in a realist manner, his use of ambiguity (imperfect or rough lines, for example) and his use of light for compositional purposes also linked him to the historic American Luminist school of the 19th century.
The Luminists tended to depict landscape scenes (in the tradition of John Constable and Joseph M. W. Turner) with a romantic sensibility, much like Jackson was doing.
The empty fields and solitary farm houses impart a sense of vastness and expanse that is enhanced by his use of perspective.