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.

Black Puma Adrian Quesada, the Austin-based guitarist, producer, and songwriter who also co-founded Grammy-winning Latin funk orchestra Grupo Fantasma, looks at the centerpiece of Willie’s 1998 album Teatro, “I Never Cared for You.” That album, produced in a small movie house by Daniel Lanois as a showcase for Willie’s guitar-picking over a bouncing bedrock of Afro-Cuban rhythms, is considered a masterpiece by Willie World insiders. A close listen by Adrian leaves him marveling at the surreal world Lanois created for the recording…but also leads to a deep examination of the Latin elements in the music of one of country’s greatest heroes—and why that makes Willie “the most American thing we have.”

New Yorker music critic Amanda Petrusich looks at the other big hit off Willie and Merle Haggard’s classic 1983 Pancho & Lefty album, “Reasons to Quit.” It’s a classic Haggard drinking song, but a little more pensive than most, and Amanda reframes it—and really, all of Pancho & Lefty—as an example of what she calls the Outlaw’s Conundrum, i.e. what’s an old rebel to do when the time comes to settle down? Then we get into the all-star band that backed Willie and Merle on the record and, in a particularly insightful interlude, the specific ways sad songs can help people when life feels like too much to bear.