The album originally contained 19 tracks of solo cuts and duets with fellow country artists, including Dolly Parton, Vince Gill and Jeannie Seely.

Hank Locklin had his greatest commercial success during the 1950s and 1960s with several well-known songs like "Send Me the Pillow You Dream On," "Geisha Girl" and "Please Help Me, I'm Falling."

[2] In the decades that followed, Locklin took a recording hiatus, mostly due to a blood cell disease that forced him to receive regular transfusions.

The album's material is mostly cover versions of previously-recorded country songs, such as "Hey Good Lookin'"[1] and "Almost Persuaded.

[5] To help revive the "classic" sound found on Locklin's early records, session musicians from his original 1960s LP's were chosen for the project.

[6] Locklin and his son bought advertisement time on the Grand Ole Opry to help promote the record, making him the first country artist to do so.

Bruce Eder of AllMusic gave Generations in Song a four-star rating in his review, calling it a "killer album".