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.