25. John Michael Montgomery

Born in 1965, John had a leg-up on his quest to be a popular singer as he was born into a musical family. He, his parents, and his brother had a family band together that toured local clubs around Lexington, Kentucky. Once John graduated high school, he began solo touring the local honky tonk circuit. At one of the popular venues in Lexington, he was discovered and signed to Atlantic Records. (John’s brother Eddie Montgomery would eventually sign with Columbia Records as half of the popular country duo Montgomery Gentry). Being blessed by starting his country music career when the genre itself was on an upswing, John had hits from the beginning and continued that streak for a decade-long radio career. John’s songs could sometimes slip into adult contemporary material (with 2 of his songs becoming huge successes for R&B group All-4-One) but his instrumentation always went more traditional. A number of John’s most popular tunes are still played on the radio and in honky-tonk bars to this day.