Overton Cheadle was born in 1919 on his father’s allotted land, as a grandson of fellow Chickasaw Hall of Famer Martin Van Buren. He graduated from Chilocco Indian School in 1937. Cheadle continued his education on athletic scholarships at Murray State College, Oklahoma City University and eventually earned his degree from what is now known as the University of Central Oklahoma and his master's degree from the Illinois Institute of Technology.

Overton joined the U.S. Navy to help fight in World War II and, while in the service, rehabilitated sailors who were injured in the war. Being a man of strong, athletic build, he also played for the Navy athletic teams.

Once his time in the service was done, Overton began an education and coaching career which spanned more than 40 years. During his career as an educator, he was a Southern Oklahoma Development Authority Employment and training specialist.

Cheadle was always serving the Chickasaw Nation in some capacity throughout his career. He was a higher education specialist for the Chickasaw Nation and active on the Chickasaw Tribal Legislature, the Chickasaw Constitution Committee, Chickasaw Nation Education Committee and the Inter-Tribal Council of the Five Civilized Tribes.

His support and service for the Chickasaw people affected the Nation so much that a scholarship was created in his name.

For his contributions, Overton Cheadle was inducted into the Iowa High School Coaches Hall of Fame, the Chilocco Indian School Hall of Fame and the Iowa State Hall of Pride.