Originally working as a cotton picker, Glosson was taught the rudiments of the harmonica by his mother before beginning his professional musical career in 1925, on KMOX Radio, in St.
[1] Glosson traveled around the Midwest for performances in small-time venues before auditioning as a cast member for WLS Chicago's National Barn Dance in 1930, alongside many other musical acts, including Gene Autry, who attempted to persuade Glosson to pursue an acting career with him, in Hollywood.
[2] He managed to become a popular local attraction for his ability to include unusually harmonic riffs and sounds in his stage act.
[citation needed] Glosson did eventually go to Hollywood to accept an opening as a radio host in 1934, but returned to the Midwest by the end of the year.
[3] In the early 1940s, Glosson composed for Molly O'Day, whom he first encountered while on Suppertime Frolic, writing songs that included "Mathew 24" and "Don't Forget the Family Prayer".