(1910-2003) Signing his work "Black Moon", Riddles' work was largely based on the Comanche people.
He was a student at Fort Sill Indian School, studying with Spencer Asah. Riddles also undertook mural instruction under Olaf Nordmark at Fort Sill. He and Cecil Murdock went to another school (Anadarko Indian School) one summer, painting murals to meet their expenses.
In 1968 Riddles was commissioned by the Southern Plains Indian Museum in Anadarko, Oklahoma to paint a series of rawhide shields and historical paintings on buckskin and elkhide.