Cunningham was born in Ennis, and studied at the Aunspaugh Art School in Dallas, the Art Institute of Chicago, and the National Academy of Design in York. He also received private lessons from Edward G. Eisenlohr, Edward J. Finley Timmons, Harry Leith-Ross, Lowell Birge Harrison, and George W. Bellows. He was a professor of art at the Waco Academy of Fine Arts. He lived for a period of time in St. Gallen, Switzerland. In 1935 he was a resident of Clarksboro, New Jersey. He died at Kerens in Navarro County.