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.

Three-time Grammy-winning, supergroup folk trio I’m With Her—whose individual members Aoife O’Donovan, Sara Watkins, and Sarah Jarosz also have an additional four Grammy wins outside the band—discuss the one Willie song they’ve covered together, “Wake Me When It’s Over.” It’s one Willie’s cut repeatedly over the years, but the version that caught the trio’s ear was off his seldom cited, 1972 album The Willie Way, which points at what’s special in this episode. It’s all about discovery, about the way that brilliant singers and pickers like Aoife, Sara, and Sarah, who happen also to be millennials, come to Willie’s music and what they find when they get there. All that, plus their excitement at playing this year’s Farm Aid in September—with brief cameos by Emmylou Harris, Bill Monroe, and George Clinton.

In a special episode taped on Willie Nelson’s ranch at last year’s Luck Reunion, Taj Mahal—a true genius of the blues and roots music from all over the world—talks about the first song on Side 2 of Willie’s 1974 masterpiece Phases and Stages, “Bloody Mary Morning.” That song and album were among the earliest, best examples of what Willie would accomplish once he broke free from Nashville, a fight for creative control mirrored by Taj’s own battles with the music industry in the late 60s. From there Taj walks us through rich memories of the fabled scene at the Armadillo World Headquarters, where both he and Willie would find a home, with extra insight coming from guest co-host Mickey Raphael, who calls Taj one of his all-time favorite harmonica players and a huge influence on his own playing—and thus a pivotal element in the revolutionary sound of Willie’s Family Band.

Eurythmic Dave Stewart, who along with his bandmate Annie Lennox—and, of course, Willie Nelson—is a member of both the Songwriters Hall of Fame and the Rock and Roll Hall of Fame, discusses one of Willie’s most beloved songs of recent vintage, “Energy Follows Thought.” The song was the standout off Willie’s great 2022 album A Beautiful Time, and one Dave loves in part for the freedom he hears in Willie’s guitar-playing, but also for its deep, spiritual message, which conjures the near-death experience that fundamentally changed Dave’s life and set his career with Eurythmics in motion. From there he hits on the paramount importance of ignoring record execs, living in the moment, and Willie’s brilliant guitar-and-vocal-only collection from 1991, The IRS Tapes.

Whisperin’ Bill Anderson, a multimillion-selling Country Music Hall of Famer, 65-year Grand Ole Opry regular, and almost certainly the only living songwriter who got to Nashville before Willie did, talks about one of Willie’s earliest entries into the Great American Songbook, “Funny How Time Slips Away.” It’s a song Willie actually pitched to Bill back in 1961, when the two were part of the generation of young songwriters—think Harlan Howard, Hank Cochran, Roger Miller, Loretta Lynn, etc.—that moved to Nashville and turned it into Music City, USA., and it prompts Bill to use Willie’s example as a masterclass in not just how to write a great song, but in country music history and Willie’s singular place in it.

Comedian Ali Siddiq zooms in on Willie Nelson’s 1979 cover of the Allman Brother’s tale of a desperate outlaw’s life on the lamb, “Midnight Rider.” It’s a song Ali used to blast in his Monte Carlo during his days as what he calls “street pharmaceutical rep” in Houston’s Third Ward, as detailed in his groundbreaking 4-part comedy special Domino Effect, and it gets him thinking aloud on American culture’s enduring fascination with gangsters and outlaws…plus such Willie-adjacent lessons as the significance of working every angle to control your destiny, and the importance of taking the gifts that save you--like comedy and music--and paying them forward to save others.

With cameo appearances by Aretha Franklin, Martin Lawrence, and Willie’s old drummer Paul English—who Ali can tell, just from looking at one photo, was an actual outlaw.