Of Irish descent, born in Butcher Hollow, near Paintsville, Kentucky in Johnson County, Oliver Lynn was an uneducated resident of a town based around the coal mining industry. Having served in the United States Army during World War II, he was uninterested in coal mining upon his return. He made a living selling moonshine, which earned him the nickname "Mooney". At age 21, Lynn met 15-year-old Loretta Webb at a pie social, and a month later they married. A year later, the newlyweds relocated to Custer, Washington as Lynn searched for better work opportunities. By the time his wife was 17, the couple had three children. Throughout the course of their marriage, the Lynns had six children: Betty Sue, Jack Benny, Clara Marie ("Cissy"), Ernest Ray, and twin girls Peggy and Patsy (the latter named after Patsy Cline). Jack Benny Lynn predeceased his parents; Betty Sue Lynn died in 2013.