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.

Before he received wide acclaim as Bob Dylan’s lead guitarist in the early 2000s, Charlie Sexton was a fixture of the Austin music scene going back almost as far as Willie himself, having first performed publicly in 1978, as a self-taught, nine-year-old, guitar prodigy invited onstage at the famous Continental Club. This week, Charlie the producer/bandleader/singer-songwriter nerds all the way out on one of Willie’s extra-obscure, early-60’s Pamper Demos, “I Let My Mind Wander,” a recording he considers a perfect example of real-deal, steel-driven, jukebox country music. But then, because we were recording our conversation in one of Willie’s old haunts, Arlyn Studios, he gets into his own experiences as a precocious preteen dragging his guitar through Willie World, before giving a little insight into how much his old boss, Bob Dylan, loves Willie Nelson.

John Mellencamp, one of Willie’s fellow Rock and Roll Hall of Fame members and a Farm Aid co-founder, has been a fan since first hearing “Funny How Time Slips Away” as a pre-teen in Seymour, Indiana. That song was one of Willie’s first contributions to the American Songbook, a reliable hit for other artists for nearly 15 years before Willie finally became a star, and it gets Mellencamp musing on parallels between early Willie and Bob Dylan—and how he later followed Willie’s lead in his own bitter battles with record industry overlords. From there we get into the unlikely origin of Farm Aid, the ongoing fight for the American farmer, and why Mellencamp thinks Willie deserves the Nobel Peace Prize.

CNN political analyst Paul Begala, a former White House chief strategist for Bill Clinton and lifelong Willie nerd, talks about “Heartland, a song Willie co-wrote and recorded with Bob Dylan for his 1993 masterpiece, Across the Borderline. “Heartland” was inspired by the American farm crisis of the mid-eighties, a tragedy Begala saw first-hand as a young speechwriter working his first presidential campaign in 1987, and one that he still has a hard time discussing. But it’s in those memories—and a gracious turn Willie did for his mom—that Begala settled on what he considers the singer’s true gift, empathy. With cameo appearances by Nelson Mandela, Elie Weisel, and Parliament-Funkadelic.