In 1936, Tipton lead a band playing on the radio station, KFXR. In 1938, Tipton joined Louvenie’s Western Swingbillies. This band played on another rado station, KTOK, and at Brown's Tavern. In 1940, Tipton was touring the Midwest and playing at dances with Scott Cameron's band. Starting in 1941, he played for two and a half years at Joplin, Missouri's Cotton Club with George Meyer's band. He then toured for a time with Ross Carlyle. Later, he played for two years in Texas.