Million-selling country star Jamey Johnson, one of the finest singer-songwriters alive and a man generally considered the walking embodiment of Outlaw Country, talks on the title-cut to Willie’s 2004 album, It Always Will Be. The song’s a simple, hymn-like ballad, and maybe not the first thing you’d think of when Outlaw comes up, but that will change when Jamey explains what the term—and this wonderful song—mean to him. From there he describes poker, chess, and domino games; huge figures in Willie’s life, like longtime stage manager Poodie Locke and legendary songwriter Hank Cochran; and what Willie means to him, both as a friend…and as an example of how to live your life.

Kenny Chesney, a Country Music Hall of Famer and longtime Willie friend, fan, and collaborator, talks about Willie’s 1976 cover of “That Lucky Old Sun.” That beautiful, hushed track, which opened the album The Sound in Your Mind, was one of Willie’s first covers from the Great American Songbook, setting the stage for his Stardust triumph two years later...and hearing it now takes Kenny back to an old tour bus, when he was a young artist studying Willie’s singing. From there he gets into the duet the two cut on the song in the mid-2000s—which ended up being a pivotal record for Willie—plus what it was like to produce Willie's 2008 album, Moment of Forever, and the way Willie helped inspire the artistic change that grew Kenny into Billboard’s Top Country Artist of the 21st Century.

Music writer John Spong talks each episode to one notable Willie fan about one Willie song they love--then runs down the kinds of rabbit holes that open up when the subject is Willie Nelson. Starting March 11, fifteen new episodes featuring Kenny Chesney, Taj Mahal, George Saunders, Tami Neilson, Dave Stewart, Jamey Johnson, Ali Siddiq, Matt Berninger, and so on…each giving a uniquely personal take on the life and art of a genuine American folk hero.

With the holiday season in full effect, we’re reaching back to OBW’s earliest days to re-up this Nov 2020 episode with Lumineer Wesley Schultz on Willie’s initial contribution to the holiday canon, “Pretty Paper.” Wes was a little kid growing up in the New Jersey suburbs when he first fell for "Pretty Paper," which his folks played in the car as they drove their neighborhood checking out Xmas lights. We talk about that, the surreal story from Willie’s own childhood that prompted him to write it--and the way only Willie could write a Christmas song you want to hear all year long.

In a special, icon-on-icon birthday tribute, 13-time Grammy winner and longtime Willie friend, fan, and collaborator Bonnie Raitt talks about their sublime 1993 duet, “Getting Over You.” It was a cornerstone of one of the most important albums of Willie’s career, Across the Borderline, and produced by the brilliant Don Was—who also produced Bonnie’s own masterpieces Nick of Time and Luck of the Draw. Bonnie gets into all that, likening Willie in the studio to both the Cheshire Cat and Yoda, before talking about covering “Night Life” with B.B. King at Willie’s legendary 60th birthday concert, why she thinks Willie is the most unique guitar player alive, and then sending him the most gracious birthday wish you will hear all year.

Brilliant indie rock-pop-and-folk singer-songwriter Conor Oberst, of Bright Eyes and Monsters of Folk fame, talks about another of Willie’s famous Pamper Demos, “Undo the Right.” It was one of Willie’s earliest efforts for the Pamper Publishing Company, a co-write with Hank Cochran, the legendary songwriter who first championed him when he moved to Nashville. That gets Conor thinking about the craft of songwriting, about how sneaking contradictory or counterintuitive ideas into songs helps them to better reflect what he calls the "big mess” of real life, and how nobody writes a bridge like Willie does…before we listen to another old Willie song, “The Storm Has Just Begun,” which was the B-side to his first single in 1959—and that Willie wrote when he was just twelve years old.

Revered photographer Mark Seliger—who’s taken iconic images of everyone from Barack Obama and the Dali Lama to Kurt Cobain and Ice T—talks about the song that he says has informed almost every photo he’s taken of his friend Willie Nelson, 1978’s “Stardust.” Mark was a college freshman on a long, lonely road trip the first time he heard it, and he describes channeling that experience, plus the work of Edward Curtis, into his first great Willie portrait nearly twenty years later. From there he gets into what you learn about Willie from a close look at Trigger, plus the wonders of playing a Fourth of July Picnic with his own country band, Rusty Truck.

Larry Gatlin, a card-carrying member of the Nashville Songwriters Hall of Fame (“All the Gold in California,” “Broken Lady,” etc.), focuses on “She’s Not for You,” off Willie’s game-changing 1973 album, Shotgun Willie. Well-read Willie nerds know that record, cut in New York for Atlantic Records, was the closest Willie had yet come to creative control of a project, and Larry, who played guitar and sang backup in the sessions, describes just how different that was from the Nashville process in which Willie'd been struggling. But he also explains another, lesser-known key to the record’s success…before sharing memories of the legendary picking parties Willie co-hosted with University of Texas football coach Darrell Royal, and the joy of just being around longtime Willie consort Roger Miller.