Cunningham was a self-taught artist who painted mostly landscapes of the coasts of Maine, New York, Nova Scotia, Michigan, North and South Carolina, Georgia and Florida.
[2] Cunningham moved to Saint Augustine, Florida in 1949[3] and opened an art gallery and curio shop.
In 1969, his work began to attract serious notice, and in 1970 was exhibited at the then Loch Haven Art Center in Orlando.
His reputation continued to grow, and a large number of his paintings were shown at the Museum of Arts and Sciences in Daytona Beach, Florida in August 1974.
His art continued to draw attention long after his death on December 29, 1977 (he committed suicide at age 84).
[5] His works were on display beginning August 10, 2007 at the Smithsonian American Art Gallery in Washington, D.C., the first stop on a national tour.
His landscapes offer flattened forms shown in profile and human images resembling doll-like figures.
It is apparent that Cunningham did not take to the advancements and modernization of the country and never showed any signs of innovation in his paintings.
[13] He achieves this feeling through strange sites, such as palm trees under snow and visions of Viking ships, along with bright colors.
This is how things seem in the minds of those who are innocent and naive to the ways of the world; this concept does not take away from the ability to enjoy the subject matter of the paintings.