Stonewall Jackson became the first entertainer to join the Grand Ole Opry without a recording contract, performing first on the Opry’s Friday Night Frolics. Backed by Ernest Tubb’s Texas Troubadours, he proved to be so popular that the audience demanded four encores. Eventually Jackson hit the road with Tubb and the Texas Troubadours. Tubb became a mentor to the young singer and songwriter.By early 1957, Jackson had cut his first record, “Don’t Be Angry.” Next the upbeat “Waterloo,” spent five weeks at the top of the country charts, hitting number four on the pop charts. Through the ‘60s Jackson was a consistent hitmaker with such country standards as “Why I’m Walkin’” (1960), “A Wound Time Can’t Erase” (1962), and “B.J. the D.J.” (1964) and “I Washed My Hands in Muddy Water” (1965).
In 1980, Stonewall signed with First Generation Records and re-recorded his hits along with new songs under the production of Pete Drake.