5 of the Saddest John Prine Songs Ever

No one could write lyrics quite like John Prine, whether about love or heartache, and some of his saddest songs of all time prove just how skillful he was in discussing the latter. From his 1971 eponymous debut to his final 2018 record ‘The Tree of Forgiveness,’ Prine’s ability to craft songs that were as beautiful as they were poignant and witty as they were heartbreaking persisted with each new release.

Although this certainly isn’t an exhaustive list of his most tear-jerking, heartstring-tugging songs, we’ve rounded up a small selection of some of the saddest John Prine songs of all time.

1. “Sam Stone”

John Prine might’ve tucked this track neatly in the middle of his debut’s A-side, but “Sam Stone” is anything but a pass-over song. Originally titled “Great Society Conflict Veteran’s Blues,” the song is a heartwrenching and, unfortunately, highly topical narrative of an opioid-addicted veteran who eventually dies from an overdose.

The final verse outlining the veteran’s overdose is easily the saddest part of this John Prine classic. Sam Stone was alone when he popped his last balloon, it begins. He ends: There was nothing to be done but trade his house that he bought on the GI bill for a flag-draped casket on a local hero’s hill.

2. “Summer’s End”

The fourth track off ‘The Tree of Forgiveness’ is full of nostalgic melancholy, and the fact that this was John Prine’s last record before his 2020 passing makes the song all the more heartbreaking. Using the physical seasons as a metaphor for the end of life, “Summer’s End” reflects on years past through holidays, imagery, and more.

Prine expertly captured this bittersweet mood in his final verse: The moon and stars hang out in bars just talking. I still love that picture of us walking. Just like that old house we thought was haunted, summer’s end came faster than we wanted.

3. “Hello In There”

Some of John Prine’s best work came from his 1971 debut, and “Hello In There” is certainly no exception. The then-25-year-old’s track about the loneliness older people face as retirement life grows mundane, children grow up and leave the house, and couples float away from one another was a poignant depiction of the “golden years.”

“Hello In There” explores the idea of older people slowly fading back inside of themselves, and he hammers this point home in the chorus. You know that old trees just grow stronger, Prine sings, and old rivers grow wilder every day. Old people just grow lonesome, waiting for someone to say, “Hello in there, hello.”

4. “6:00 News”

Another tragic song from his eponymous first album, John Prine’s “6:00 News” starts with a mother, Wanda, having a baby. At face value, the first two verses wouldn’t seem to qualify this song as one of Prine’s saddest. But eventually, he reveals the son Wanda had was a closeted homosexual, which Wanda discovers after reading his diary.

Sneaking in the closet and through the diary, Prine sings in the last verse. Now, don’t you know all he saw was all there was to see. The whole town saw Jimmy on the six o’clock news. His brains were on the sidewalk, and blood was on his shoes.

5. “Bruised Orange (Chain of Sorrow)”

The title track of John Prine’s 1978 album ‘Bruised Orange’ begins with a story about a local alter boy who had been hit by a commuter train. A group of mothers gathered around the scene, waiting to see if it was their son. “I always remember the look on one mother’s face…the others had a big sigh of relief. They tried to comfort the other one, but they were too relieved to be very comforting,” he says in the album introduction. 

Prine addresses the difficulty of comprehending the unfairly premature death of a young boy in the chorus: You can gaze out the window, get mad and get madder, throw your hands in the air, say, “What does it matter?” But it don’t do no good to get angry, so help me, I know. For a heart stained in anger grows weak and grows bitter, Prine continues. You become your own prisoner as you watch yourself sit there wrapped up in a trap of your very own chain of sorrow.

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