Credit: Leon Morris/Redferns

When “Little” Jimmy Scott—a rare genetic condition earned him the nickname—died in his sleep at his Las Vegas home last week at 88, the man Madonna once called “the only singer who makes me cry” left behind a legacy as beautiful and sad and strange as his voice.

Born third in a family of 10 and ­orphaned by age 13, the Cleveland native went on to record with artists from Charlie Parker to Lou Reed, and sang (the same song, “Why Was I Born?,” 40 years apart) at both Dwight Eisenhower’s and Bill Clinton’s inaugurations.

Label troubles led to a career lull in the ’70s and ’80s, and he took a series of menial jobs—fry cook, busboy, hospital orderly—until an early-­’90s resurgence brought new work, including collaborations with fans including Reed and Bruce Springsteen and an ­unforgettable cameo in Twin Peaks’ series finale.

For Scott, the song was always the thing: “If it tells a story, and I’m interested in the story,” he told EW in 1996, “then it’s a go.”

Below, stream a playlist of some of his best classic and covers: