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.

Nine-time Grammy-winner and bona fide reggae royalty Ziggy Marley talks about the closing track on Willie’s 1993 masterpiece, Across the Borderline, “Still Is Still Moving to Me.” It’s a song to be dug on multiple levels, from the hard-driving melody, to the koan-like lyrics, to Trigger’s stunning runs, and Ziggy gets into all that. But his focus is on the song’s message, which he calls “transcendent”—just like his friend, Willie. So even though reggae and country music aren’t all that different in Ziggy’s mind, neither are they relevant. Because to him, Willie is one of those artists—like his dad, Bob—who rises above genre to create a music that’s universal. Note that Ziggy also gets into one of those things that you can’t transcend, and that’s the rules at Willie’s poker table…as he found out the hard way.