Sometime in the early 1970s, Willie Nelson went to a party in Nashville, where he met Jerry Wexler, the legendary producer and record executive. Wexler was one of those figures whose name you might not know—but whose impact you’d certainly recognize: As a partner in Atlantic Records in the 1950s, he’d helped record and market Black artists like Ray Charles and The Drifters to white audiences, categorizing their music as “rhythm and blues” at a time when most people were still calling it “race music.” He’d also helped guide Aretha Franklin to greatness—producing or co-producing almost all her music between 1967 and 1972—and had assisted in signing Led Zeppelin. As Wexler saw it, Nelson’s problem was that he didn’t have enough freedom to express his ideas, leading the singer to sign with Atlantic. But Nelson’s first attempt for the label, a gospel album called The Troublemaker, would be rejected outright, prompting another conversation with Wexler: “You’ve praised the Lord,” the exec told him. “Isn’t it time to give the devil his due?” The resulting album, 1973’s Shotgun Willie, isn’t just one of the first statements in what you could call “outlaw country.” It’s also a snapshot of a particular scene at a particular time. Having left Nashville after the house fire that inspired 1971’s Yesterday’s Wine, Nelson enmeshed himself in the musical community in Austin, Texas, where the mix of country, soul, folk, and jazz reflected not only Nelson’s omnivorousness, but also the laid-back spirit that came to define his place in the culture, and that’s captured on Shotgun Willie. The title track is a 12-bar-blues portrait of a dude biting on a bullet in his underwear; “Whiskey River” is a classic country lament recast as early-1970s funk; and “Sad Songs and Waltzes” offers the warm glow of a country-rock crossover anthem. The humor here is part Western, part psychedelic fortune cookie, and the album finds the common ground between the live-and-let-live looseness of old-time America and the progressivism of its newer, longer-haired generation: Both want the freedom to do whatever they damn well please. Alongside bands like The Flatlanders—check out the extraordinary More a Legend Than a Band—and albums like Jerry Jeff Walker’s ¡Viva Terlingua! and Waylon Jennings’ Honky Tonk Heroes, Nelson’s Shotgun Willie marks the beginning of alternative country.