Eurythmic Dave Stewart, who along with his bandmate Annie Lennox—and, of course, Willie Nelson—is a member of both the Songwriters Hall of Fame and the Rock and Roll Hall of Fame, discusses one of Willie’s most beloved songs of recent vintage, “Energy Follows Thought.” The song was the standout off Willie’s great 2022 album A Beautiful Time, and one Dave loves in part for the freedom he hears in Willie’s guitar-playing, but also for its deep, spiritual message, which conjures the near-death experience that fundamentally changed Dave’s life and set his career with Eurythmics in motion. From there he hits on the paramount importance of ignoring record execs, living in the moment, and Willie’s brilliant guitar-and-vocal-only collection from 1991, The IRS Tapes.

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.