Malcolm McKesson was born in Monmouth Beach, New Jersey at the summer house of his wealthy New York City family.[He completed the Grand Tour of Europe twice before turning eighteen, and these trips piqued his interest in art history, which he later studied at Harvard University. His grandfather died in 1924 and his eldest brother in 1927.
Madeline Mason died in 1990. Three years later, McKesson approached dealers at the New York Outsider Art Fair. Although he did not necessarily think of himself as an outsider, based on the other work he had seen there, he felt that here was an audience that might appreciate him. Wikipedia