John Prine's 10 Greatest Songs

by Julian Spivey
It was announced on Saturday, Jan. 12 that John Prine would be inducted into the Songwriters Hall of Fame, which was somewhat of a shock to me because I would’ve assumed he would already have been an inductee. In celebration of Prine’s terrific body of work here are his 10 greatest songs. Prine’s 1971 self-titled debut was such a perfect album that half of this list comprises of songs from that all-time classic album. 

10. “In Spite of Ourselves”
John Prine can write a tragedy ballad like no one else in songwriting history, but he also has a terrific sense of humor and wit that comes out in his work and his 1999 duet with Iris DeMent “In Spite of Ourselves” is a great example of this. “In Spite of Ourselves,” originally written for Billy Bob Thornton’s film “Daddy and Them,” is a wildly strange, but lovely duet with two unique voices that mesh perfectly together. 

9. “Christmas in Prison”
Most Holiday songs are cheerful, but that isn’t how everyone spends the Holidays. This is why I love John Prine’s contemplative song off his third album 1973’s Sweet Revenge about a prisoner spending the “happiest time of the year” in prison and dreaming of a love that’s outside of the bars. Prine’s evocative lyrics have a way of putting you in the shoes of the narrator and you can feel the pain in this one. 

8. “Lake Marie”
“Lake Marie,” from 1995’s Lost Dogs and Mixed Blessings, is one of the most unique songs in John Prine’s discography as it kind of melds multiple stories into one song and takes an abrupt turn by the end. The first verse tells the story of Lake Marie, on the Illinois-Wisconsin border where Prine used to visit growing up. The second verse tells of meeting a girl at the lake, falling in love and later returning to try to revive their relationship. The third verse sees the song getting macabre with news of a murder on the television. It’s an incredibly interesting, literary and mysterious track.  

7. “Souvenirs”
“Souvenirs,” off of John Prine’s sophomore release Diamonds in the Rough from 1972, is a beauty of nostalgia that proves that nostalgia isn’t always fun and games, but sometimes full of memories you’d rather keep deep down. 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” are just mesmerizing, which is why it’s all the more surprising that Prine claims he wrote this in 20 minutes in a car on the way to a club show in Chicago simply because he thought he should have a new song each night so the usual crowd wouldn’t tire of him. 

6. “Paradise”
“Paradise,” off of John Prine’s 1971 self-titled debut, is likely his most covered song and the countriest sounding song of his career. “Paradise” tells the tale of being taken to a place called Paradise in Kentucky as a childhood by his father and how the town, which was a little perfect slice of Americana, was eventually bought out and destroyed by a coal company. Prine says he wrote the song for his father, “so he would know I was a songwriter.” “When the song came on, he went into the next room and sat in the dark while it was on. I asked him why, and he said he wanted to pretend it was on the jukebox,” Prine said. 

5. “Summer’s End”
“Summer’s End,” released just last year on John Prine’s first album of original material in more than a decade The Tree of Forgiveness, shows that Prine hasn’t missed a step in his songwriting despite taking so much time off. “Summer’s End” is a devastating slice of nostalgia with a narrator pleading for a lost love or friend or family member to come on home. For someone who’s 72-years old like Prine the “summer” in the song could also be a stand-in for time and life passing by so quickly. “Summer’s End” was recently nominated for a Grammy Award for Best American Roots Song. 

4. “Sam Stone”
“Sam Stone,” from John Prine’s debut album in 1971, is another of his most covered selections having been recorded by legends like Johnny Cash. The song, which a Rolling Stone magazine poll ranked as one of the saddest songs of all-time, tells the story of a war vet who returns home and becomes addicted to heroine and ultimately dies of an overdose. It’s a story so many actual vets could identify with. 

3. “Six O’clock News”
“Six O’clock News” isn’t really a John Prine prime cut like so many of the others on this list, but the song from his debut album has always been one of my personal favorites, and one that’s always been somewhat mysterious for me. “Six O’clock News” tells the story of James Lewis, who finds out a mysterious secret in his mother’s diary and commits suicide. Prine said the song is based on a childhood friend who was a troublemaker and ended up in Juvenile Court where the prosecutor preceded to tell the court, and him, that his father was indeed his father, but his mother was actually his older sister.” 

2. “Angel From Montgomery”
John Prine’s “Angel From Montgomery” tells the story from the point of view of an old woman looking back on her younger days and a past love and missing it all. The song includes a couple of my all-time favorite Prine lyrics: “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.” Perfection. The song found wide recognition when Bonnie Raitt covered it beautifully in 1974. 

1. “Hello In There”
It always mesmerizes me when a songwriter can completely get into the mindset of his characters and their lives and feelings and John Prine does this better than most on his 1971 tune “Hello In There,” off his debut album. “Hello In There” tells the story of an older, retired couple and the loneliness of the old after their careers are over and all their children have moved away. It’s achingly sad, while beautifully written and it amazes me that a guy in hid mid-20s could understand this loneliness of the elderly so perfectly. We knew right off the bat that Prine was truly something special.