Despite being born in a privileged home, Randolph dropped out of high school to work on left-leaning publications.

He pursued graduate work at Clark University and received a Master of Arts degree in psychology.

He later dedicated his book Ozark Superstitions (1947) to the memory of his Clark mentor G. Stanley Hall.

[2] In 1927, Randolph had his first article published in the Journal of American Folklore, based on work on Ozark dialect and folk beliefs.

His Ozark Mountain Folks (1932) describes the creation of a distinctive church choir singing style created by a corps of uncredentialled, itinerant choral instructors.