5. "Luckenbach, Texas (Back to the Basics of Love)"
Jennings didn't play an actual gig in Luckenbach until July 4, 1997, two decades after he recorded this mid-tempo ballad about rekindling the flame in a small Texas town. That didn't stop him from turning the tune into a nostalgic, heartrending tribute to the simpler things in life, anchored by big, booming, baritone vocals and a tip of the cowboy hat to pre-outlaw pioneers like Hank Williams and Jerry Jeff Walker (who recorded a live album, Viva Terlingua, at the Luckenbach Dancehall in August 1973). Willie Nelson even got a piece of the action, singing the song's final verse while prepping fans for the Waylon and Willie album that would appear one year later.