Riddle was born in Lynchburg, Tennessee, in Moore County, to Martin Van Buren and Theresa (née Tucker) Riddle, and raised in Tennessee until he enrolled in school at National Normal University in Lebanon, Ohio.
Riddle decided his future would be made in the West, and moved to that part of Indian Territory containing the town now known as Chickasha, Oklahoma.
He established a private practice of lawyers that was retained on most of the important legal cases that appeared before the territorial courts before the state of Oklahoma was organized.
[3] During the eight months following his appointment, he reportedly wrote eighty opinions, a number never exceeded by an Oklahoma justice in such a short time.
[3][b] Frances was noted for her equestrian skills and won a blue ribbon at the Oklahoma State Fair in 1914.