As the title suggests, it features Jennings' performances of songs written or made famous by Hank Williams. The album was recorded and mixed by Rodney Good and produced by Jennings in 1992 at Eleven Eleven Sound Studios in Nashville, Tennessee. Very few copies of the release were ever pressed, making the original album extremely rare today. In his autobiography Jennings recalls, "I felt chills all over me the first time I heard Hank Williams sing 'Lost Highway.' I would stay up late on Saturday night listening for him, happy if I could just hear him speak. I always wanted to be a singer, but he etched it in stone," and admits, "Musically, Hank Williams was my centerpost. It's always gone back to him, the one who did everything wrong and everything right.
Jennings also cited Williams as a critical interest on the Outlaw movement:
"If I had an Outlaw hero, someone to set my standard and measure my progress, it was Hank Williams...Everything I did, anything anyone did, was measured against Hank's long, lanky shadow. You'd hear these stories, how he pulled a jukebox that didn't have his records on it out to the street and shot it full of holes, or ran around all night dead drunk and pilled out and still gave the greatest show you ever saw. We thought that was the way you did it...I wanted to be like him.
Jennings also cited Williams as a critical interest on the Outlaw movement:
"If I had an Outlaw hero, someone to set my standard and measure my progress, it was Hank Williams...Everything I did, anything anyone did, was measured against Hank's long, lanky shadow. You'd hear these stories, how he pulled a jukebox that didn't have his records on it out to the street and shot it full of holes, or ran around all night dead drunk and pilled out and still gave the greatest show you ever saw. We thought that was the way you did it...I wanted to be like him.
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