Just a few days before he passed away this past April, at the age of 69, songwriter Jesse Winchester got to hear his final album. “[Jesse] wrote me an email that I will treasure for the rest of my life saying how happy he was with the record, and that he wouldn’t change a note,” says Mac McAnally, who produced Winchester’s album, A Reasonable Amount of Trouble. The LP will be posthumously released on September 16th.
Winchester, whose songs have been recorded by artists like Waylon Jennings, George Strait, Reba McEntire and Emmylou Harris, had only recently overcome a 2011 diagnosis of esophageal cancer when he began work on a new record in May of 2013. “When we began recording, Jesse had a clean bill of health, and there was a joy, a feeling that he had gotten past the worst of it. He said he didn’t want to make a ‘Hey, I think I’m dying’ record,” says McAnally. The producer, songwriter and acclaimed session musician was approached by Winchester to work on the album after producing Quiet About It, a 2012 tribute record to Winchester that featured Lyle Lovett, Lucinda Williams and Rosanne Cash.
Despite his strong desire to avoid making a gloomy record of “songs about dying,” several of the songs Winchester brought to McAnally were reflective, mournful meditations that he had written in the midst of his previous bout with cancer. To help lighten the mood, the singer-songwriter decided to record several of his favorite doo-wop songs from his youth, like 1955’s “Devil or Angel” by the Clovers and 1962’s “Rhythm of the Rain” by the Cascades. “Jesse said, ‘I don’t want to wait until I have time to write songs about how happy I am right now,'” says McAnally. “He said, ‘I just want to sing something happy, because I’m happy.'”
The resulting record, A Reasonable Amount of Trouble, is a gentle collection of playful songs about love, memory and gratitude that amounts to one of the most moving, triumphant albums of Winchester’s 45 year career. After recording the basic tracks for the album, Winchester’s health took a tragic turn when cancer reappeared in his bladder in early 2014. “Instead of trying to finish the record so that Jesse could tour, eventually, and imminently, the goal became trying to finish the record so that he could hear it,” says McAnally.
One of the most chilling tracks on Winchester’s last studio album is “Every Day I Get the Blues,” a ruminative, sparse recording that finds Winchester gently crooning over the song’s aching melody. “The first time I heard that song, it hit me like a baseball bat,” says McAnally of the tune, which Rolling Stone Country is premiering below. “His voice, which he was worried about sounding weak during the recording sessions, becomes so haunting in that song.”
McAnally remembers another particularly heavy moment during the recording sessions, when the Louisiana-born singer was playing the album-closing devotional “Just So Much,” a song that includes the line “I’m dying to find Him, but dying’s my fear.” “We’re all Southern boys who aren’t inclined to tear up,” he says. “But when Jesse would sing that song we’d try not to boo-hoo, because he’s so good at writing about what’s really going on his life.”