When John Prine died in April 2020, the world lost one of its greatest songwriters. After breaking onto the scene with his self-titled 1971 debut, Prine barely put a foot wrong for the rest of his career, releasing one great song after another. Frequently compared to Bob Dylan (who’s confessed to being a major fan), he combined wry humor with devastating observations to create one of the most beautiful collections of songs in music history. Here, we pay tribute to his extraordinary talent with our pick of the 10 best John Prine songs of all time.
Souvenirs is the kind of song with lines like “broken hearts and dirty windows/make life difficult to see/that’s why last night and this mornin’/always look the same to me.” In other words, it’s poetry in motion, laced with bittersweet nostalgia and more world-weariness than any 26-year-old (the age Prine was when he wrote it) has a right to. What makes it all the more extraordinary is that Prine wrote it in just 20 minutes in the back of a cab on the way to a gig, simply because he thought he needed to write a new song every night to stop the crowd from losing interest.
Prine wrote Paradise after visiting his parents in Kentucky and witnessing the devastation caused by strip mining around the Green River in the eastern part of the state. He was originally reluctant to record the song, which references the town of Paradise in Muhlenberg County, Kentucky, because he “didn’t think anybody would be able to pronounce Muhlenberg.” Fortunately, he did, and the song has since been covered by numerous artists, most notably Lynn Anderson, who took it to No. 26 on the Billboard country chart in 1976.
8. Illegal Smile
As Paste Magazine points out, who else besides John Prine could have the wit and wherewithal to sing the line, “A bowl of oatmeal tried to stare me down, and won?” Full of observational humor and set to the backdrop of honky-tonk guitars, it’s a little piece of escapist heaven. Most of his fans have concluded that the song is about drugs. Prine said it was simply about his ability to find the funny in things that other people couldn’t. Whether you believe him or not, there’s no question it’s a sublime song.
7. Far From Me
Culturesonar.com calls Prine’s self-titled debut album “stone-cold perfect.” Listening to tracks like Far From Me, it’s hard to disagree. In a sight departure from the folky roots of other tracks like Sam Stone, Far From Me is a country-esque melody full of heartbreak and reflection. Prine’s charcoal rasp is in fine form, adding an extra punch to the wry observations that pepper the song.
6. Christmas in Prison
You’d usually expect a song with Christmas in the title to be full of festive cheer, but Christmas in Prison isn’t your usual holiday tune. Written about a prisoner dreaming of his love while spending the “happiest time of the year” enjoying “turkey and pistols made out of wood” behind bars, the only cheerful thing about the song is Prine’s exquisite turn of phrase. Initially released on his 1973 album Sweet Revenge, Prine revisited the track over 20 years later on his 11th studio album, A John Prine Christmas.
5. Sam Stone
When someone like Johnny Cash covers a song, you know it’s a song worth listening to. Sam Stone is certainly that, even if it is quite possibly one of the biggest tear-jerkers of modern times. Written about a war veteran who succumbs and eventually loses his life to heroin addiction, it wrestles with weighty topics without becoming overwhelmed by them. Poised, elegant, and utterly heartbreaking, it stands out as one of the finest moments of Prine’s extraordinary debut album.
4. Speed of the Sound of Loneliness
Few songs in John Prine’s back catalog have been recorded quite so many times as Speed of the Sound of Loneliness. Listening to the original, you can see why. Written about the breakdown of a marriage, it’s intense enough to be almost painful at times, especially in lines like “How can a love that’ll last forever / Get left so far behind.” Originally recorded for Prine’s 1986 album German Afternoons, he later revisited it with Nanci Griffith on her 1993 album Other Voices, Other Rooms.
3. Angel From Montgomery
Angel From Montgomery is written from the perspective of a middle-aged woman who finds herself trapped by marriage and domesticity and longs for an angel to come to take her away from it all. With lines like “If dreams were lightning and thunder was desire/this old house would’ve burned down a long time ago” and “How the hell can a person go to work in the morning/and come home in the evening and have nothing to say,” it’s understandable why Prine was so often compared to Bob Dylan throughout the course of his career. Originally included on Prine’s 1971 debut album, it drew fresh attention when Bonnie Rait released an incredibly sympathetic cover on her 1974 album, Streetlights.
2. Lake Marie
Named by the LA Times as one of Prine’s best songs, Lake Marie is a dazzling piece in which Prine interweaves stores of myth and fate and death with more depth and more poise than most songwriters could even dream of. Bob Dylan has called it one of his favorite songs of all time. It’s not hard to see why.
1. Hello In There
Finally, we come to Hello in There, a song that ranks among Prine’s best known and most extensively covered creations. It tells the story of an old, retired couple whose children have flown the nest and who spend their days “Waiting for someone to say, ‘Hello in there, hello.'” For someone in their mid-20s to so perfectly capture the loneliness of old age was jaw-dropping back in 1971, and it’s still extraordinary to this day.