He moved to Pineville, McDonald County, Missouri in 1919. He never moved away from the Ozarks and remained in the Ozark Mountains from 1920 until his death. He met his first wife in McDonald County, Marie Wardlaw Wilbur, and made a living by writing for sporting and outdoor publications. While writing, Randolph used pseudonyms, but never for his work on the Ozark culture.

In 1927, Randolph had his first article published in the Journal of American Folklore, based off work on Ozark dialect and folk beliefs. The dialect work led to multiple publications throughout the 1920's and 1930's in American Speech and Dialect Notes. In 1947, Randolph had his first major book release, published through Columbia University, Ozark Superstitions.

Pissing in the Snow and Other Ozark Folktales was a national bestseller. He published over a dozen works on Ozark folklore. He was elected a Fellow of the American Folklore Society in 1978. He married Mary Celestia Parler in 1962. He died in 1980 in Fayetteville, Arkansas.