Gary Winstead, the youngest of eleven children, was born in 1948 and grew up in Pontiac, Illinois, an obscure farm town in the middle of the Illinois Corn Belt. At the age of eighteen, he joined the United States Marine Corps and served for four years, rising to the rank of corporal (E-4) before earning his honorable discharge.
He went on to receive a bachelor’s degree in physical education, a master’s in educational administration from California State University, Fullerton.

He is a roper (header) and member of the USTRC and National Senior Rodeo Cowboys Association. He is married to his wife Jerasol and lives in Southern California.
He is also a producer and director:
The Pony No One Could Ride is his first film. Welcome To Frogmore is his second film and Riding Through Life With Love By My Side is his third.