The Best John Prine Songs Are a Testament to the Human Experience

John Prine could turn monotony into a mountain. His songs found beauty in simplicity—the monumental struggle of everyday life and the tragedy and triumphs of moments big and small. He idolized Hank Williams and Roger Miller and he took from them a respect for the working man and the stories they have to tell and made it his own.

Prine started writing songs when he was a teenager, and continued to do so through his time serving as a mailman before and after the Vietnam War. (Drafted in 1966, he was stationed in West Germany for a time.) He was relatively unknown until 1970, when a young breakout named Kris Kristofferson heard him playing in a Chicago club. At the age of 23, Prine had already developed a Steinbeckian power of language and storytelling. And for the next half century, until his death on Tuesday due to complications from coronavirus, he wrote hundreds of songs—many of them folk and country staples. When he was first hospitalized in late-March, Adrianne Lenker and Joan Baez paid tribute to Prine with covers of his work.

He's idolized by the likes of Bob Dylan, who, in a 2009 interview said “Prine’s stuff is pure Proustian existentialism. Midwestern mind trips to the nth degree. And he writes beautiful songs.”

It's true that every John Prine song is essential in its own way, but we went through and picked out 10 of the most powerful, comforting, and transcendent to remember him. They cover mental health, PTSD, poverty, love, heartbreak, and the entire spectrum of the human condition.