During the 1930s, the Drifting Cowboys varied from one show to another, with members playing a few shows before leaving and being replaced. The original line-up consisted of Braxton Schuffert (guitar), Freddie Beach (fiddle), and the comedian Smith "Hezzy" Adair. The youngest member of the band was thirteen-year-old steel guitar player James E. Porter.

He was born with spina bifida occulta, a malformation of the spine which caused him lifelong pain and was a factor in his later abuse of alcohol and drugs.

When he was just eight years old, Hank met Rufus "Tee-Tot" Payne. According to legend, Rufus would come around and play Hank's guitar, showing him how to improvise chords. This early exposure to blues and other African American influences helped Williams successfully fuse hillbilly, folk and blues into his own unique style.

By the time Hank arrived in Montgomery in 1937, he had decided to drop his given name, Hiram, in favor of Hank. According to one of his first steel guitarists, Boots Harris, he'd say that "there was a fence outside his house and he'd sleep with the window open, and there was an old cat walking up and down that fence yowling 'H-a-r-r-m-m, h-a-r-r-m-m.' He said he thought the cat was calling him so he changed his name to Hank." The truth was, of course, that "Hank" sounded more like the name of a western music star than "Hiram."

"I'm a Long Gone Daddy" laid the blueprint for what would become the typical Williams A-side: an up-tempo honky tonk song in the Ernest Tubb tradition with a bluesy edge. The song was recorded in anticipation of a recording ban that would result from the American Federation of Musicians possibly calling a strike at the end of 1947 when agreements with all the record companies expired.

After all of his band members were drafted to serve in WWII (he received a 4-F deferment because of his back) Williams began showing up to the show intoxicated, and the station fired him for "habitual drunkenness".

After meeting at a medicine show, Williams and Sheppard married in 1944 at a Texaco Station in Andalusia, Alabama. Although the ceremony was performed by a justice of the peace, it was later declared illegal because Sheppard's divorce from her previous husband did not comply with the legally required 60-day trial reconciliation.

Williams performed "Hey, Good Lookin" on the Kate Smith Evening Hour on March 26, 1952. The appearance remains one of the few existing film clips of the singer performing live. He is introduced by Roy Acuff and banters with a young June Carter, wearing his famous white cowboy suit adorned in musical notes.

During one of his concerts, Williams met his idol, Grand Ole Opry star Roy Acuff backstage. Acuff warned him of the dangers of alcohol, complimenting his musical talent but questioning his decision-making abilities.

Although the pseudonym was meant to distinguish Williams' gospel recordings from his more popular country music, Williams insisted on performing his "Luke the Drifter" songs during his regular concerts.