Nevertheless he was a dedicated, self-conscious artist who after 1949 kept his paintings all together without selling them in a museum next to his antique store. The work itself is remarkable, and well rewards close looking. Cunningham worked through his deficiencies as a representational painter, turning his limited mimetic capacities to account within a painterly style based on patterned topographical composition and bold coloristic effects. His painting is ambitious even beyond his means, a style which economically evokes the real. The works are overtly simple.
All land is clearly visible.
All ships are shown in shooting gallery profile. As in the draftsmanly ship portraits done by the Bard brothers and other 19th-century painters, Cunningham's ships are never coming or going, but always passing by. All paths and roads are shown entire, as lines without a break. Cunningham's work might be read as the kind of pictorial wish-making that is fulfilled by property ownership. In fact, he yearned for a houseboat.