Randolph County was primarily settled by migrants from the Upper Southern states, especially Kentucky and Tennessee. They brought slaves and slaveholding traditions with them, and quickly started cultivating crops similar to those in Middle Tennessee and Kentucky: hemp and tobacco. Randolph was one of several counties settled mostly by Southerners to the north and south of the Missouri River. Given their culture and traditions, this area became known as Little Dixie, and Randolph County was at its heart.
Randolph County is home to one of the nine, and last, 5-star U.S. Generals of the American military, Omar Nelson Bradley.
There were 9,199 households out of which 31.40% had children under the age of 18 living with them, 52.70% were married couples living together, 11.10% had a female householder with no husband present, and 32.20% were non-families. 27.90% of all households were made up of individuals and 13.10% had someone living alone who was 65 years of age or older. The average household size was 2.43 and the average family size was 2.94.
In the county the population was spread out with 23.80% under the age of 18, 9.60% from 18 to 24, 29.30% from 25 to 44, 22.40% from 45 to 64, and 14.80% who were 65 years of age or older. The median age was 37 years. For every 100 females there were 107.50 males. For every 100 females age 18 and over, there were 108.10 males.
The median income for a household in the county was $31,464, and the median income for a family was $39,268. Males had a median income of $26,878 versus $20,366 for females. The per capita income for the county was $15,010. About 9.20% of families and 12.50% of the population were below the poverty line, including 17.10% of those under age 18 and 13.20% of those age 65 or over.