By the mid-1970s, John Prine was in a creative rut. The singer had grown so disillusioned with Atlantic Records that he asked Ahmet Ertegun to let him out of his contract in 1975. After that, Prine tried to make a rock album, and failed. Feeling tapped out, he called Steve Goodman—his old friend from the Chicago folk scene, and the writer of “City of New Orleans”—and asked for help producing the album. The result was 1978’s Bruised Orange, which many Prine fans consider the songwriter’s best. Goodman brought Prine back to basics, removing the backup singers and horns found on 1975’s Common Sense, and convincing him to record near his home in Chicago. “All you gotta do is show up every day,” said Goodman, according to Clay Eals’ biography Steve Goodman: Facing the Music. “I won’t ask you to do anything dumb or stupid. Just do what I ask you to do, and I can give you a really good record.” The album kicks off with “Fish and Whistle,” on which Prine joyfully recalls his old job at a drive-in burger joint, and life in the military (“I was in the Army, but I never dug a trench/Used to bust my knuckles on a monkey wrench.”) “Bruised Orange (Chain of Sorrow),” meanwhile, was inspired by Prine’s childhood experience of visiting a police scene where a young altar boy had been struck by a commuter train while walking to work. And on “Sabu Visits the Twin Cities Alone,” Prine uses the story of Sabu Dastagir—an elephant rider who became a short-lived film star in the 1940s—to talk about the loneliness of being a touring musician. Making Bruised Orange wasn’t easy. According to Eals, Prine and Goodman at one point got into a shouting match about creative direction at their hangout, a Chicago bar called the Earl of Old Town. But the resulting album would be a highlight of Prine’s career—and a testament to the two musicians’ close bond. “At night, I’d go home not thinkin’ that we had anything from the studio,” Prine said. “But when Steve mixed the whole thing and played it for me, here he gave me a beautiful record. Steve didn’t have to prove his friendship to me, but that’s where he came through.”