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7 Songs by the Late, Great John Prine You Should Know

Losing a legend is never easy. Saying farewell to somebody like John Prine feels like a grim task for the ages.

Prine passed away on April 7 due to complications from the coronavirus, his publicist confirmed. While technically “old” at 73, he seemed well and had a busy 2020 touring schedule ahead of him. I was lucky enough to see the artist last September at the Portland Zoo, where he treated the crowd to a fine performance of classic Americana and the small stories in between that make each song so special. He played songs from his excellent latest album, Tree of Forgiveness, and talked about how much he enjoys drinking beer and fishing.

john prine
Rich Fury/Getty Images

The list of musicians pouring one out for Prine cannot be counted. The Illinois-born songwriter had some of the biggest fans in the business. Dylan has talked about Prine as one of his all-time favorites. Johnny Cash revered him. Roger Waters has said he’s one of the most moving musicians he’s every listened to. Kris Kristofferson was so enamored by Prine’s potential that he helped bring him to the fore (in fact, the country icon was so taken by Prine that he famously said his songs were so good “we’ll have to break his thumbs”).

Great musicians create great music but legendary ones reshape it. Prine was a master lyricist, concocting compelling narratives that had depth, humor, and humility. He was part of a Chicago scene that steered country music toward social activism and political activism, in subtle and often beautiful ways. And he did it all without ever losing his charm and genuine sense of humor. 

I wrote this for the New York Times about our friend and hero ⁦John Prine.

— Jason Isbell (@JasonIsbell) April 9, 2020

As a kid, Prine went to folk school in Chicago and later served in the army. He returned to civilian life as a mailman and hobby musician before turning out a fantastic debut LP in 1971. In retrospect, it makes perfect sense that Prine delivered mail door to door. His songs were so relatable, observational, and essential, just like a good mailman.

His musical career took flight in the open-mic circuit of the Windy City. Film critic Roger Ebert caught one of his early sets and is believed to be one of Prine’s first big fans. It was the beginning of what ended up being a five-decade career in music. 

Throughout, Prine was an astute storyteller and found pureness in relatable impurities. He founded his own record label in 1981, fed up with the system as it was. He battled cancer successfully in 1998 but it took some of his neck and some valuable tongue nerves, too, making his voice rockier. He was married to Fiona Whelan Prine, who managed his band.

He passed away in Nashville earlier this month after an extended hospital stay related to COVID-19. Amid the masks, social distancing, and gruesome news cycles, we need his steady voice more than ever. Fortunately, he wrote a lot of immortal music.

In short, you should visit or revisit every Prine record. But here are a few tracks of note, should you not know them already:

“Sam Stone”

John Prine - Sam Stone

The song Prine’s most famous for stands up as a timeless country anthem. It’s a heartbreaking tale of a veteran-turned-addict with one of the best lines in all of music: “There’s a hole in daddy’s arm, where all the money goes.” Just Prine and his trusty guitar, the song is so intimate that it feels internal, as though it’s strumming and singing inside your gut.

“Illegal Smile”

John Prine Illegal Smile

Illegal Smile is a reminder of all the great things classic country has. The track boasts a good story, a fetching melody, tear-jerking twang, and stark honesty. It’s a bit tongue-in-cheek and while it seems like a number about smoking weed or drinking to escape, it’s more about the strange power of simply smiling when others don’t to shift the atmosphere.

“Fish and Whistle”

John Prine - Fish & Whistle (studio version)

A buoyant song about the joys of the simpler things, this track touches on the highs and lows of working class American life and how some time on the water and a good meal can remedy just about every struggle. It almost feels like a soundtrack to Prine’s life (or, at least the score to his outlook on life).

“In Spite of Ourselves”

John Prine and Iris DeMent - In Spite of Ourselves (Live From Sessions at West 54th)

A gorgeous, gently shuffling song, this duet perfectly captures the domestic struggle. There’s even a bright ending, with rainbows and some semblance of togetherness. It’s hilarious, tender, bittersweet, and a little absurd, not entirely unlike marriage.

“Saddle in the Rain”

John Prine - Saddle In The Rain

This robust song is almost a big band number, with galloping guitar hooks and brass and percussion to boot. It’s proof that his music translated well beyond just the Americana mold, into pop-rock and soul. It’s amazing how even amid all the sound in this rich song, Prine’s voice is still alpha. 

“The Great Compromise”

John Prine - The Great Compromise

Perhaps the most Dylan-esque track of the Prine portfolio, “The Great Compromise” would be right at home on the track list of Highway 61 Revisited.

“When I Get to Heaven”

John Prine on Austin City Limits "When I Get to Heaven"

It’s unbelievably fitting that he finished with this delightful track. A jolly, parlor house folk number with reflective commentary, the song is a look at how Prine imagines the next big step. It concludes his last record and opens the pearly gates to what we all hope is an afterlife filled with fishing buddies, riding the tilt-a-whirl, and smoking a cigarette that’s nine miles long.

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