Martie Maguire and Emily Strayer, founding members of 13-time Grammy winners and American musical-and-cultural icons The Chicks, discuss their favorite Willie Nelson song to play together, “Bloody Mary Morning.” That song was, of course, a key track on Willie’s revolutionary 1973 LP Phases and Stages, a concept album depicting a divorce from a wife’s POV on Side 1, and a husband’s on Side 2, and we walk through its songs, paying special attention to Willie’s telling of the woman’s side of the story and just how true it rings. But they also describe being little girls watching their grandparents slow dance to Willie records on the old family farm, memories from time on Willie’s bus when they toured together in 2000, and the surreal, star-studded scene backstage at Willie’s 90th birthday shows at the Hollywood Bowl back in 2023.

In a re-airing of one of OBW’s early greatest hits, legendary producer, bass player, and Blue Note Records president Don Was looks at the title track to one of the best, most important albums of Willie’s career, Across the Borderline. It’s a song Don suggested to Willie in late 1992, when he was essentially auditioning for the production job on Willie’s next album—which he got—and it gets Don thinking on the fragile magic of a perfect first take, what it’s like to go out to dinner with Willie and Ringo Starr, and the unusual sleeping arrangements Willie often makes when he’s out on tour. Oh and it’s worth noting that Don, who also produced the B-52s’ “Love Shack” and Bonnie Raitt’s “I Can’t Make You Love Me,” among a great many other songs, calls “Across the Borderline” his favorite track that he ever worked on.

As the man who has directed stage lighting at Willie Nelson shows for just under 50 years, Buddy Prewitt—better known in Willie World by the nickname the boss gave him, Budrock the Illuminator—is an absolutely essential member of Willie's famous “band of gypsies.” Fittingly enough, in this episode he focuses on a song that he says tells his own life story, “On the Road Again.” His stories from a half-century with Willie are first-hand, fantastic, and often surreal, starting with the first show he accidentally ended up working, at the Louisiana Superdome in 1977, running up to this past summer’s 4th of July Picnics. In between come countless rounds of golf, a hug for Julio Iglesias, a funnel for the crew’s bus, and memories of Sister Bobbie, drummer Paul English, stage manager Poodie Locke, and the people at a Willie show who matter most to Willie: the fans.