Dollar relocated to Dallas in the early 1950s, where he worked in trucking and in a lumber yard. In 1952 he recorded a single for D Records, but it didn't catch on, and Dollar then found work as a DJ in Louisiana and New Mexico. There he began fronting a group called the Texas Sons and performed on the Louisiana Hayride in the middle of the 1950s. Following this he played with the Light Crust Doughboys, but soon returned to Dallas, where he began performing in the nascent style of rockabilly. Working with promoter Ed McLemore and songwriter Jack Rhodes, he recorded a number of songs, but they were never issued, and Dollar soon left music, taking up work as an insurance salesman in Oklahoma.
Dollar married and divorced four times, and was an alcoholic; late in his career he acquired throat cancer, and the operations destroyed his ability to sing. He committed suicide on April 13, 1986.