From his earliest work in the 1950s to today, Willie looks back at the songs that have defined his career, from his days of earning $50 each to his biggest hits, from his less well-known songs (but incredibly meaningful to him) to his concept albums. Along the way, he also shares the stories of his guitar Trigger, his family and “family,” as well as the artists he collaborated with, including Patsy Cline, Waylon Jennings, Ray Charles, Merle Haggard, Ray Price, Dolly Parton, and many others.

Willie is disarmingly honest—what do you have to lose when you’re about to turn 90? —meditating on the nature of songwriting and finding his voice, and the themes he’s explored his whole life—relationships, infidelity, love, loss, friendship, and, of course, life on the road.