This album was recorded during Willie Nelson's transition from Nashville to Austin, Texas, reflecting his growing desire for artistic control. The sessions took place at RCA Studios in Nashville and at Bradley's Barn in Mount Juliet, Tennessee.
The album's title comes from a song Nelson wrote, and the record includes a mix of new compositions and covers of country classics. Despite its quality, the album did not achieve major commercial success at the time, as Nelson was still consolidating his 'outlaw' sound.
This work is considered a bridge between his RCA period and his later success with Atlantic Records. The album cover shows Nelson with a more casual look, moving away from the polished Nashville image.