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 Carlile, 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.