The irony that one of his finest records would be released in 1978, during the punk-rock movement, would not be lost on John Prine, a key architect of the Americana music scene. Prine’s career had been guided by numerous logic-defying moments. After Roger Ebert wrote about him in his newspaper column (Ebert reportedly snuck out of a bad movie to see him play), Prine got a record contract with the help of Kris Kristofferson, already an esteemed outlaw-country singer-songwriter. Kristofferson was taken to a club where Prine was playing by a friend of Prine’s, Steve Goodman (who would go on to write “Go, Cubs, Go” and “A Dying Cub Fan’s Last Request”).

Kristofferson described his being blown away by Prine’s songs in the liner notes to Prine’s self-titled debut album. Released in 1971, the album is full of spellbinding character-based stories. Prine could imagine desperate lives unfolding—and unraveling—in real time. “I am an old woman named after my mother,” begins “Angel from Montgomery,” a song whose simplicity and clarity has made it into many a performer’s set. “Sam Stone,” about a morphine-addicted Vietnam vet, had a similar lyrical craftsmanship; Prine later noted that he chose the character’s last name because it could be followed by “coming home.”

If there was any problem with his first record, that in many ways equaled Kristofferson’s first (also self-titled), it was that the songs shone in spite of, rather than because of, their rather standard arrangements. That problem was solved when Goodman produced Bruised Orange, and found ways to complement Prine’s songwriting. Goodman opened up the sonic palate beyond country-music staples such as strings and pedal steel guitar, inserting brass and woodwind instruments.

A lucky accident created the opening song, “Fish and Whistle,” a longtime fan favorite. Prine explained,

I was asked to write one more song for an album I thought was done already. And I thought, well, I’ll write the worst thing I can think of. And then maybe the producer will decide the record’s over with. So I wrote three different unrelated verses. None of them—they’re all true, but none of them relate to each other. And then I tied them together with an unrelated chorus and somehow it worked.

I’d argue that the storytelling on Bruised Orange is as imaginative as anything Prine had done before. That’s not to say, however, that the previous albums after his debut didn’t have inspired moments (I’d propose his second album, Diamonds in the Rough, released in 1972, deserves a critical reappraisal), but it largely felt as if Prine had a tendency to fall back upon a position of cool detachment.

“That’s the Way That the World Goes ‘Round” shifts split-second from anxiety to comedy when the character’s being trapped in a bathtub when the water suddenly freezes is freed by the ice being melted by the sun’s arrival. The song encapsulates Prine’s philosophy, which regards the daily absurdities of life as keys to grasping its meaning. This sort of Midwestern stoicism (Prine was formerly a Chicago mailman) could have a sarcastic edge. Some songs from previous albums could be accused of laughing at, rather than with, the haplessness of the characters presented therein.

While “Sabu Visits the Twin Cities Alone” feels like a set-up for Prine’s humor—”Sabu was sad the whole tour stunk/The airlines lost the elephant’s trunk”—the song takes a compassionate view of a performer lost and out of place “in the land of the wind chill factor.” Sabu is not just an outsider, like so many of Prine’s characters; he’s in a culture of which he has little prior knowledge. And Prine wisely doesn’t enter into Sabu’s headspace, instead giving us the perspective of the crowd he attracts, which makes us complicit in his ongoing humiliation.

The show-stopping “Bruised Orange (Chain of Sorrow)” starts with the temperature drop of a failed romance: “My heart’s in the icehouse.” The protagonist then remembers an event from his childhood (taken from Prine’s own life), witnessing, while on his way to shovel snow at a church, a train fatally colliding with an altar boy, who never saw it coming. Now in adulthood, the protagonist is pained by feelings he can’t control, only able to brace for final impact:

I been brought down to zero, pulled out and put back there.

I sat on a park bench, kissed the girl with the black hair

And my head shouted down to my heart

‘You better look out below!’

To respond by getting mad, however, only makes things worse, Prine advises in the refrain:

For a heart stained in anger grows weak and grows bitter.

You become your own prisoner as you watch yourself sit there

Wrapped up in a trap of your very own

Chain of sorrow.

Goodman works his magic throughout the song, blending hymnal organ chords into the layers of guitars. The song is capped off with a beautiful soprano saxophone solo that enters the picture at first surprisingly, then feels like it’s the center, what the song is all about.

Call it zen, perhaps—Prine’s music here, even while focused on desperate characters, expresses the grace of a folk waltz. He sticks with the courage of his convictions; anger will lead to sadness, when you realize that how you feel about the world doesn’t mean the world will change.

Still Prine who, on his debut album, sang, “Blow up your TV,” maintains an anti-authoritarian stance. The elegiac closer, “The Hobo Song,” on Bruised Orange notes a double tragedy—not only have people sacrificed (too) much to live freely, they’re rarely remembered, except in the songs about their disenfranchised lives:

Down through the years

Many men have yearned

For freedom

Some found it

Only on the open road

So many tears of blood

Have fell around us

’cause you can’t always do what you are told.

Is this punk rock by other means? Certainly, Johnny Cash, who helped give Kristofferson his start, was revered by punk musicians such as Joe Strummer of The Clash. Go to any punk-rock show nowadays, and you’re likely to find someone wearing a shirt with the iconic photo of Cash with his middle finger raised.

But I think Bruised Orange defies any obvious labels—unless you’d argue that songs as heartfelt as these belong to a kind of timeless category of their own. Maybe Bob Dylan, never a bad person to consult on these sorts of questions, said it best of Prine: “Midwestern mind-trips to the nth degree.” Prine shows us, on Bruised Orange, all of the ways these trips can begin and end.