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.

This week, we ring in Willie’s monumental 90th birthday with his son, acclaimed singer-songwriter Lukas Nelson, who discusses “I Never Cared for You.” It’s a favorite deep-cut of true Willie lovers, a song he’s recorded repeatedly through the years; the original, 1964 single was the record that first made Leon Russell a Willie fan. But Lukas focuses on the 1998 version off Teatro because he was nine years old and in the studio when it was recorded, a memory that prompts thoughts on Emmylou Harris’s harmonies, cave paintings, and covering Pearl Jam with his dad.

This week, we wrap up the special Live from Luck! mini-season of OBW with California-based singer-songwriter Natalie Mering—known to fans by her stage name, Weyes Blood—who will discuss another standard off of Stardust, Kurt Weill's 1938 composition, “September Song.” It’s a classic that Natalie discovered the same way Willie did, through a Frank Sinatra record, and it prompts crystal clear memories of the night she first heard Willie’s version and the way her appreciation of the song changed there and then. From there we get into the unlikely backstory of how Willie recorded it, with digressions on Lindsey Buckingham, Elvis, and Greek yogurt.

This week, in the third installment of OBW’s special, Live from Luck! mini-season, Brooklyn-based singer-songwriter Steve Gunn discusses the penultimate track on Red Headed Stranger, “Hands on the Wheel.” It’s the song with which Willie wraps up the RHS narrative, when his roaming, vengeful preacher finally finds love and a home. And Steve, who first made his name as a virtuoso guitarist, focuses on the way Willie used subtle guitar-picking to bring the story to a ruminative, peaceful end...before getting into where he hears Django Reinhardt’s influence on Willie’s playing and why Trigger sounds like no other guitar in the world.

This week, in the second installment of OBW’s special, Live from Luck! mini-season, hardcore honky-tonker Charley Crockett talks about Willie’s little-known 1961 recording of “Face of a Fighter.” It’s another old Pamper demo, a barroom weeper Willie never did get around to cutting for a proper album, but one that, in Charley’s opinion, is so strong that if just about any other country artist had come up with it, it’d be the best song they ever wrote. From there he’ll get into the Willie songs he listened to as a homeless busker playing subway platforms in New York City, and the night a Willie song almost—not quite, but almost—kept him from going to jail.