3 Timeless John Prine Songs that Continue to Teach Us the Art of Songwriting

It’s likely that John Prine is your favorite songwriter’s favorite songwriter. The Maywood, Illinois-born artist could seemingly do more with an acoustic guitar and a pad of paper than just about anyone. Simple and clean, there was a purity to his work that came out in every lyrical line, every guitar-chord strum.

As a result, many of his songs remain timeless—including these three below—and listening to them is like a graduate course in learning how to write. Where should a chord change be? How should the pre-chorus sound? What about vocal inflections? Well, it’s all there in his word.

Here, we wanted to explore three such songs that continue to not only entertain but enlighten and teach, too. Indeed, these are three timeless John Prine songs that continue to teach us about the art of songwriting.

[RELATED: John Prine: The American Songwriter Interview]

“Angel from Montgomery” from John Prine (1971)

Piano and organ blend into subtle percussion and John Prine begins to sing about the life of an older woman near the end of her life. What does she want? To be free. To have an angel come down and let her escape from her life, if just for a short time. The hardships of life are everywhere but to escape with the divine—now that’s something to wish for. And Prine’s song explicates this feeling perfectly, and as a result has been covered countless times, from Dave Matthews to John Denver to Bonnie Raitt. On the track he sings,

I am an old woman
Named after my mother
My old man is another
Child who’s grown old

If dreams were lightning
And thunder were desire
This old house would’ve burned down
A long time ago

Make me an angel
That flies from Montgomery
Make me a poster
Of an old rodeo
Just give me one thing
That I can hold on to
To believe in this livin’
Is just a hard way to go

“Sam Stone” from John Prine (1971)

Another from Prine’s 1971 self-titled debut LP, this song, which Prine wrote after getting out of the army in the 1960s, is about another army man whose nerves are shattered, has shrapnel in his knee, and is still affected by drugs. The Purple Heart winner is stricken with addiction and must deal with the sad malaise that comes when you get back from a conflict like Vietnam. It’s a lovely portrait of a downtrodden American, highlighted by Prine’s country voice and finger-picked guitar. On it he sings,

Sam Stone’s welcome home
Didn’t last too long
He went to work when he’d spent his last dime
And Sammy took to stealing
When he got that empty feeling
For a hundred dollar habit without overtime
And the gold rolled through his veins
Like a thousand railroad trains
And eased his mind in the hours that he chose
While the kids ran around wearin’ other peoples’ clothes

There’s a hole in daddy’s arm where all the money goes
Jesus Christ died for nothin’ I suppose
Little pitchers have big ears
Don’t stop to count the years
Sweet songs never last too long on broken radios

“Christmas in Prison” from Sweet Revenge (1973)

While this song isn’t necessarily about being in an actual prison, it’s about that feeling. And then December 25 rolls around and you’re supposed to feel joyous and happy but you’re still stuck where you are. It’s a feeling so many know, despite trying to find cheer at the end of the year. As a result, it’s a song so many can relate to, not for saccharine cheer but for real grit. And Prine adds a little escape hatch in the song—if only the singer could connect with his true love. That would turn the prison into something much better. He sings,

It was Christmas in prison
And the food was real good
We had turkey and pistols
Carved out of wood
And I dream of her always
Even when I don’t dream
Her name’s on my tongue
And her blood’s in my stream

Wait awhile eternity
Old mother nature’s got nothing on me
Come to me
Run to me
Come to me, now
We’re rolling
My sweetheart
We’re flowing
By God

When you purchase through links on our site, we may earn an affiliate commission.

Photo by Larry Busacca/Getty Images