This week, one of America’s greatest living poets, singer-songwriter Lucinda Williams, celebrates the easy beauty of one of Willie’s most cherished songs, “Angel Flying Too Close to the Ground.” From there she’ll get into how inspiring it was to first see Willie do his thing when she moved to Austin in 1974; how weird it was, when she moved back to Austin in the 80s, to live in a run-down apartment complex-cum-artist’s colony that Willie owned on South Congress—sharing it with the old boyfriend, Clyde Woodward, she would immortalize in her song, “Lake Charles”—and what an absolute honor it was, twenty years later, to cut a duet with Willie on another of her songs, “Overtime.”

This week, Willie’s first-born, daughter Lana Nelson, talks about one of the songs her dad used to sing to her at bedtime, “Red Headed Stranger,” calling his breakthrough 1975 recording of it one of the first times an album of his sounded the way he did at home. From there she’ll walk us through some wonderful family history...like dodging rent-hungry landlords during the lean years, her dad’s hog farm/commune outside Nashville through the RCA years, and the session with Merle Haggard that produced “Pancho and Lefty.”

This week, one of the brightest stars of the Texas Country/Red Dirt scene, singer-songwriter Wade Bowen, examines “Me and Paul,” Willie’s 1971 chronicle of the road-warrior life he was sharing with his erstwhile partner in crime, drummer Paul English. It’s a perfect song for Wade to get into, partly because, as he rightly points out, Willie was a progenitor of the circuit where he makes his living now, but also because of the setting for our visit: Wade zoomed in from his tour bus, which was broken down somewhere in Iowa on his way to a gig.

This week, six-time Grammy-winning producer, songwriter, and virtuoso guitarist John Leventhal—see Shawn Colvin’s A Few Small Repairs; his wife, Rosanne Cash’s The River and the Thread—discusses the song that first hipped him to the genius of Willie, 1975’s “Blue Eyes Crying in the Rain.” He describes it with a producer’s ultimate praise, calling it a record that seems to exist outside of any era, before getting into his session work with the Hall of Fame band that backed Willie on 1993’s Across the Borderline, plus the reasons he thinks of Willie as a cross between legendary Nashville guitarist Grady Martin and Pablo Picasso...and his late father-in-law, Johnny Cash, as a cross between Elvis and Abe Lincoln.

This week, one of Willie’s longtime tour mates, Grammy-winning blues singer and guitarist Susan Tedeschi, talks about a deep cut off his 1998 album with Daniel Lanois, Teatro, “Somebody Pick Up My Pieces.” It’s a song she and her husband, slide-guitar hero Derek Trucks, play almost nightly with their group, the Tedeschi Trucks Band, and it gets her thinking aloud on a foundational principle of Willie World: The absolute importance of making music with people you love—with meaty cameo appearances by the Allman Brothers Band, Jessica Simpson, The Notre Dame Cathedral in Paris, and Emmylou Harris...who Susan calls a “Jedi.”

Singer-songwriter Bruce Robison is famous for writing highly intelligent, richly detailed country songs—that happen also to be incredibly sad. (See “Angry All the Time,” by Tim McGraw and Faith Hill, and “Travelin’ Soldier,” by the Chicks.) This week, he focuses on a track that first taught him how emotionally sophisticated country music can be, “Walkin,’” off Willie’s 1974 masterpiece, Phases and Stages...before describing his own Willie tribute song, “What Would Willie Do,” and the weird reception Willie got in Bruce’s hometown, rural Bandera, Texas, when he moved his band and family there after fleeing Nashville in 1971. (Hint: The hippies and rednecks didn’t start getting along until Willie got to Austin a year later.)

This week, Pulitzer Prize-winning author Lawrence Wright talks about a Willie hit of recent vintage, 2011’s “Roll Me Up and Smoke Me When I Die.” That may seem an odd focus song for Larry, a New Yorker staff-writer known for tackling topics like Scientology and the rise of radical Islam, but he’s also a native Texan who’s written whole books on the Texas myth. In that vein, he’s got deep, personal thoughts on how Willie’s most truly subversive move was to wear his hair—in the 70s in Texas!—in long, braided pigtails; the existential quality of watching him and Trigger grow old together; and the weirdly difficult role Larry played in getting a Willie statue erected in downtown Austin.

Booker T. Jones is one of the true geniuses of American music, a Rock and Roll Hall of Famer as a keyboardist, composer, and bandleader (see “Green Onions,” “Soul Man,” “Sitting on the Dock of the Bay,” etc.), but also as a producer, which is the role he played in the creation of Willie’s 1978 masterpiece, Stardust. It was a highly improbable pairing and production, and on this OBW episode, Booker explains all of it—how he met Willie, how they picked the songs, how they ended up recording in Emmylou Harris’s living room—with a focus on the Hoagy Carmichael classic, “Georgia on My Mind.”

In addition to being one the few artists to earn an EGOT—i.e. win an Emmy, Grammy, Oscar, and Tony—Whoopi Goldberg also happens to be a big-time music nerd and monster Willie fan. On this episode she talks about his 1978 recording of “Stardust,” calling it “a love song to a love song” that, when Willie sings it, makes her feel like she’s floating barefoot in the clouds with her late mom and brother. From there she’ll describe growing up a musical omnivore in NYC (see Waylon and Willie...but also Anthony Newley, Glen Campbell, and the Four Tops), the origins of country music, and the night she shared a stage with Willie, Leon Russell, and Ray Charles.

This week, Nick Offerman—noted actor, humorist, author, woodworker, canoe paddler, and agrarian philosopher—talks about Willie’s 1968 song, “Buddy.” It’s likely an obscure title even to real-deal Willie nerds, but not to devoted fans of Nick’s old show “Parks and Recreation,” who should recall it as Ron Swanson’s favorite song. Nick’s going to explain why “Buddy” was chosen for a key moment in what he calls the show’s most important episode, and then he’ll describe the magic of his first Willie concert, the vital work of Farm Aid, and why he considers Willie Nelson one of the greatest Americans who ever lived.

This week, Nashville super-producer Dave Cobb, whose work with some of the true artists in modern country music—Sturgill Simpson, Chris Stapleton, Brandi Carlisle, Jason Isbell—has earned him nine Grammys, talks about “Time of the Preacher.” It’s the overture/aria to Willie’s classic Red Headed Stranger, an album that Dave calls a beautiful, barren landscape, and it gets him thinking about Pink Floyd, the real definition of “outlaw,” and the most important instrument an artist can take into the studio: A belief in themselves.

On October 16, 1992, just two weeks after famously ripping up a photo of the pope on SNL, Sinead O’Connor was booed off the stage at a Bob Dylan tribute at Madison Square Garden. Willie Nelson was also on the bill that night, and after watching that happen, he invited her to join him in the studio the next day. In this clip from OBW S2E2, producer Don Was gives the story behind the duet they recorded, a cover of Peter Gabriel and Kate Bush’s “Don’t Give Up.”

This week, Americana singer-songwriter Waylon Payne talks about Willie’s 1970 cover of Joni Mitchell’s iconic “Both Sides Now.” Waylon, an NPR-darling as an artist now, grew up in Willie World; his mom, Sammi Smith—of “Help Me Make It Through the Night” fame—played package shows with Willie in the ‘70s; and his dad, Jody Payne, was Willie’s lead guitarist for almost forty years. Waylon walks us through all that, describing the way Willie songs were his lullabies as a kid, the incredibly difficult personal trials when he says Willie saved his life, and the time Willie paid his songwriting the highest praise possible. Note: the compliment wasn’t remotely suitable for small ears.

This week, Foo Fighters lead guitarist and Shred with Shifty podcast host Chris Shiflett discusses one of the original outlaw anthems, Willie and Waylon’s 1976 version of “Good Hearted Woman,” exploring the evolution of the movement and the creation myth behind the song’s recording, before grabbing a guitar and demonstrating what makes Willie an absolute one-of-a-kind guitar player.

This week, 8-time Grammy-winner Ray Benson—one of Willie’s best friends since moving his Western Swing band, Asleep at the Wheel, to Austin back in 1973...at Willie’s urging, no less!—talks about a song Willie and the Wheel cut back in 1999, the Bob Wills classic, “Going Away Party.” Wills was, of course, a hero to both Willie and Ray, as was the song’s composer, the great Cindy Walker, who Ray calls one of the single greatest influences on Willie’s own songwriting. From there he’ll describe fifty years of friendship and collaboration with Willie, with cameos by George Gershwin, Floyd Tillman, and Robert Duvall.

This week, singer-songwriter and virtuoso fiddle player Amanda Shires talks about the title song to her new album of duets with Willie’s sister, pianist Bobbie Nelson, “Loving You.” It’s the only song Sister Bobbie ever wrote, a solo piano instrumental with a melody that Amanda says is all about love, faith, and family. She also talks about how Bobbie was one of her heroes long before they became friends and made this record, a role model as a trailblazing female in a male-dominated industry, as a musician more generally, as a mom...and just as a person.

This week, we ring in Father’s Day with Willie’s youngest son, singer-songwriter and visual artist Micah Nelson, who talks about “Still Is Still Moving to Me.” It was the closing track on his dad’s landmark 1993 album Across the Borderline, a high-octane, guitar-heavy anthem that kicked off the Living Legend phase of Willie’s career. Micah describes how much fun it is to play every night as part of the Family Band, before describing the drive to create he inherited from his dad, one of his dad’s favorite Roger Miller stories, and the magic of discovering old Willie records that others have forgotten.

Dr. Brené Brown is a researcher, storyteller, and best-selling author known for her work on vulnerability, shame, and empathy—though many of her fans just call her “an inspiration.” On this week’s OBW, she talks about Willie’s 1976 cover of “Amazing Grace” and the way her life was completely transformed the first time she heard it...before we move into the song’s history; her lifelong love of Willie; the concepts of faith, grace, and acceptance, more generally; and the most powerful performance of “Amazing Grace” she’s ever heard.

This week, one of the greatest, most innovative record producers in history, Daniel Lanois—think U2’s The Joshua Tree, Bob Dylan’s Time Out of Mind, Peter Gabriel’s So—talks about the landmark album he made with Willie, 1998’s Teatro. He’ll start with a deep cut, “I’ve Loved You All Over the World,” but then, being Lanois, he’ll start to float...to Cuban dance clubs, Texas honkytonks, and Mexican movie houses...to art that exists only in shadows...and to the way U2 tries to summon Willie when they write songs.

This week, legendary singer-songwriter Ray Wylie Hubbard—one of Willie’s oldest running buddies and a founding father of Americana music—talks about the signature song that opens every Willie show, “Whiskey River.” It might as well be the national anthem of Texas, but for Ray it prompts some highly personal, absolutely hilarious memories of times he’s heard Willie play it, before sending him deep into that time he was kidnapped by Willie’s road crew, the reasons drummer Paul English was NOT a fan of the Eagles...and Willie’s smile.