Whisperin’ Bill Anderson, a multimillion-selling Country Music Hall of Famer, 65-year Grand Ole Opry regular, and almost certainly the only living songwriter who got to Nashville before Willie did, talks about one of Willie’s earliest entries into the Great American Songbook, “Funny How Time Slips Away.” It’s a song Willie actually pitched to Bill back in 1961, when the two were part of the generation of young songwriters—think Harlan Howard, Hank Cochran, Roger Miller, Loretta Lynn, etc.—that moved to Nashville and turned it into Music City, USA., and it prompts Bill to use Willie’s example as a masterclass in not just how to write a great song, but in country music history and Willie’s singular place in it.

Comedian Ali Siddiq zooms in on Willie Nelson’s 1979 cover of the Allman Brother’s tale of a desperate outlaw’s life on the lamb, “Midnight Rider.” It’s a song Ali used to blast in his Monte Carlo during his days as what he calls “street pharmaceutical rep” in Houston’s Third Ward, as detailed in his groundbreaking 4-part comedy special Domino Effect, and it gets him thinking aloud on American culture’s enduring fascination with gangsters and outlaws…plus such Willie-adjacent lessons as the significance of working every angle to control your destiny, and the importance of taking the gifts that save you--like comedy and music--and paying them forward to save others.

With cameo appearances by Aretha Franklin, Martin Lawrence, and Willie’s old drummer Paul English—who Ali can tell, just from looking at one photo, was an actual outlaw.

Celebrated author George Saunders digs deep into one of the best-loved songs not just in Willie Nelson’s catalog, but in all of American music, Townes Van Zandt’s legendary tale of betrayal, “Pancho and Lefty.” It is, in many ways, a song full of mystery, and George, who also teaches Russian short fiction at Syracuse University’s acclaimed creative writing program, walks us through it verse-by-verse, unlocking the secrets in the song’s story; the way Townes, Willie, and Merle Haggard made us care so much; and what the song tells us about what it means to be human. All that, plus the way hearing “Hello Walls” as a little kid crawling around under his parents’ poker table awakened him to the importance of elegance in art—with cameos by Dostoevsky, Chekov, Jeff Tweedy, and Ernie Banks.