The Luke the Drifter songs were recorded at various sessions between January 1950 and July 1952 at Castle Studio in Nashville with Fred Rose producing.

Williams' immense popularity and unflagging commercial success left Rose and MGM no choice but to indulge his wish to record the recitations, and the first session, held on January 10, 1950, produced four songs: "Too Many Parties and Too Many Pals," "Beyond the Sunset," "The Funeral," and "Everything's Okay."

Williams recorded three songs under the guise of Luke the Drifter that are considered classics: "Ramblin' Man," "Pictures from Life's Other Side," and "Men with Broken Hearts."

Perhaps the most well known Luke the Drifter song is "Ramblin' Man," a rare, minor key dirge that features a taut, edgy vocal from Williams as he sings about wanderlust and loneliness.

His keening falsetto and Harold Bradley's steel guitar echoed the song's sentiments, but it also contained a folk edge atypical for a Hank Williams recording.

Bruce Eder of AllMusic wrote: "for those unfamiliar with them, the songs are all well-chosen and they work within the context of devotional and cautionary songs, Williams easily slipping into this mode of performance, usually with a gospel organ accompaniment and very understated steel guitar - the one mood-breaker, much closer to Williams' secular material, is the upbeat, dark-humored, almost comical 'Everything's Okay,' which basically holds that 'we're still a-livin'/so everything's okay.'"