After hearing Jackson’s demo tape, Wesley Rose, president of Acuff-Rose Music, arranged for Jackson to audition for the Grand Ole Opry. Jackson became the first artist to join the Grand Ole Opry before obtaining a recording contract. He toured with Ernest Tubb, who became his mentor. Jackson signed with Columbia Records in 1958.
His breakthrough came in the Country Top 40 in late 1958, with a song written by a young George Jones, “Life to Go”. It peaked at No. 2 in early 1959 and his follow-up record, “Waterloo”, was No. 1 for five weeks, and crossed over into the Top 40 of the Billboard Hot 100 chart, where it reached No. 4. The track also reached No. 24 in the UK Singles Chart in July 1959. It sold over one million copies, and was awarded a gold disc. The song was a haunting and catchy tune that states “Everybody has to meet his Waterloo”, meaning their fate. The song cites Adam, Napoleon and Tom Dooley as examples.
His next No. 1 hits came in 1964 with “Don’t Be Angry” and “B.J. the D.J.” (Jackson’s foray into the teenage tragedy song trope, about an over-worked Country music radio station disc jockey, who crashes his car in a rainstorm). In 1971, Jackson was the first artist to record a live album from the Grand Ole Opry with Recorded Live At The Grand Ole Opry. His other hit songs include “The Carpet on the Floor”, “Why I’m Walkin'”, “A Wound Time Can’t Erase”, and “I Washed My Hands In Muddy Water”. Jackson also recorded a cover version of Lobo’s 1971 hit, “Me and You and a Dog Named Boo”, which became Jackson’s final top 10 hit.
From 1958 to 1971, Jackson had 35 Top 40 Country hits.
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