Born in Jacksonville, Texas, Dexter owned a bar in the 1930s and helped popularize the style of country music known as honky tonk. He made his recording debut on November 28, 1936 for ARC Records. and he was probably the first artist to use the term "honky tonk" in a country song when he recorded "Honky Tonk Blues" at his first session. His tremendous hit "Pistol Packin' Mama" became the 1943 marching chorus of the New York Yankees. The 1943 movie of the same name, made by the Republic Pictures, gave Dexter close to $250,000 in royalties. Another hit from the 1940s was "Guitar Polka", which entered Billboard's list as the "Most Played Juke Box Folk Record" for 16 weeks running in 1946. Still other hits include "So Long Pal", "Triflin' Gal", "I'm Losing My Mind Over You" and "Too Late to Worry."