Cherry was born in Kerens, Texas on August 7, 1901. He played his high school ball at Weatherford High School and later attended Texas Christian University in Fort Worth in the early 1920s and was a three-sport star. Upon graduation in 1924, he had a brief professional baseball career but soon entered the coaching profession. In 1936, he married Florence Snodgrass of Amarillo, with whom he had two children.