I can’t have been the only one who, after hearing that John Prine died recently, immediately listened to “Your Flag Decal Won’t Get You Into Heaven Anymore.” There are other songs of his far more appropriate to the moment — more mournful and somber. But I wanted to hear the John Prine that put a wry smile on my face, that allowed me to laugh at the goddamned absurdity of it all.

There is a reason the song, included on his debut album almost fifty years ago, remains one of his best-known. Prine wrote it while working as a letter carrier in Chicago in the late ’60s. Of all the mail he carried, he hated Reader’s Digest the most; it weighed down his bag and was oddly shaped enough that he couldn’t get it in the mailboxes. When the publication started giving out free American flag stickers in an effort to drum up popular support for the Vietnam War, his hatred increased. Thus, the song.

Hearing it as the coronavirus surges in the United States, it is striking how adaptable the song is to this moment. Maybe it’s because we’ve been hearing for weeks that the United States is “at war” with the virus, or Donald Trump bluster that he is a “wartime president,” while so many people, the vast majority working-class or poor, are dying because of his indifference. In any event, hearing Prine’s savage sarcasm, his image of Heaven filled up with the needlessly killed, his reminder that all the cheap patriotism in the world won’t save a single soul or life, was the right way to mourn. Particularly because Prine’s death was the result of complications from COVID-19.

Prine had a talent for locating the most unique characteristics of a mundane human experience. At the center of every one of his songs was a vivid portrait of someone whose emotional complexity doesn’t fit into neat categories.

Other songs on that same self-titled album exemplify this. “Illegal Smile” was originally written about Prine’s childhood penchant for smiling at the strangest things. It was frequently mistaken as an ode to smoking weed; Prine loved the interpretation so much, he couldn’t bother to correct it. Linkages like these are peppered throughout the album, a reminder of the forgotten overlap between country music and late ’60s counterculture, before the Right started to colonize the genre.

Then there were the tender, bittersweet, often painful stories he was able to weave: “Sam Stone,” “Hello In There,” “Paradise,” his signature “Angel From Montgomery,” tales of people and places left behind, whose connection with the world has been severed. In their surroundings, whether in a kitchen with flies or strip-mined Kentucky hillsides, Prine found a stillness and strange wonder. His spare yet warm guitar style always put human beings back in the center, painting them as vibrant, fragile, strangely beautiful, and yet beautifully recognizable.

The list of songwriters — not just in folk and country but across genres — who found themselves charmed by Prine is a long one. All seem shocked and enchanted by the kind of beauty and wisdom he was able to conjure in his songs.

Kris Kristofferson wrote in the original liner notes of Prine’s debut that he was “twenty-four years old and writes like he’s two-hundred and twenty.” None other than Bob Dylan called Prine’s songs “pure Proustian existentialism,” and the description fits throughout his albums.

Describing his third release Sweet Revenge, Robert Christgau put his finger on this absurd sensitivity: “Prine is described as surrealistic and/or political even though the passion of his literalness is matched only by that of his detachment: inferential leaps and tall songs do not a dreamscape make, and Prine offers neither program nor protest.” Rather, it was the songwriter’s fascination and identification with his wounded and awkward subjects that allowed his songs to be described as “weird” or “political.”

By this time, Prine’s songs had taken on a hard-edged, cynical tinge, even while retaining a kind of compassion that had begun sounding worse for wear. It had only been two years since his debut album, but something turned in the songwriter. In interviews, Prine spoke of Sweet Revenge’s bitterness as a reaction to how critics who had once held him up as a darling subsequently panned his sophomore album Diamonds in the Rough.

But there was something else there. The title track opener quoted Hunter S. Thompson’s Fear and Loathing: On the Campaign Trail (“And the milkman left me a note yesterday / get out of this town by noon. / You’re coming on way too soon, and besides that / we never like you anyway”). He was jabbing back at the critics, but it also seemed built into a broader curdling of hope in America as the 1970s unfolded. It isn’t difficult to hear Prine bristling as country music’s mainstream was being led by the nose into the arms of American conservatism.

Vietnam would continue to show up as a subject on his albums. Prine’s Pink Cadillac (1979) — far more an early rock and roll album than country — featured “Saigon,” a song that plays with turning a vet’s trauma into a dive bar pickup line:

You got everything that a girl should grow
I’m so afraid to kiss you I might lose control
You can hold me tighter but turn loose of my gun
It’s a sentimental present all the way from Saigon

It’s a deliberately uncomfortable listen, like an avatar for the country’s stubborn insistence it keep moving forward at the expense of the most vulnerable.

Five years later, on Aimless Love, he was searching Reaganism for a soul in “People Puttin’ People Down.” It’s not exactly what Dylan would describe as a “finger-pointing song” — Ronald Reagan himself doesn’t make an appearance. Instead, Prine takes issue with the mindset of his supporters, whose identity is so tied to being better than someone else, the inanity of their worldview playfully rendered:

People without love — sometimes build a fence around
The garden up above — that makes the whole world go ’round
But all the people who don’t fit
Get the only fun they get
From people puttin’ people down

There are echoes of this in “Some Humans Ain’t Human,” a song released some two decades later on Fair & Square:

Some humans ain’t human
Some people ain’t kind
You open up their hearts
And here’s what you’ll find
A few frozen pizzas
Some ice cubes with hair
A broken popsicle
You don’t want to go there

Prine extends the puckish imagery to church-going hypocrites and back-biters looking to screw others. Nobody in particular — until he mentions “some cowboy from Texas” starting a war in Iraq.

It’s easy then to understand the parameters of John Prine’s music and what motivated him to write it. He loved people, found us to be beautiful and flawed, our pains and hopes worthy of respect. At the same time, and for the same reasons, he hated cruelty and those who exacted it. It’s a fairly simple moral compass, able to yield so many vivid stories over the span of fifty years because so little in the world has gotten better.

There’s a certain painful irony in his dying now, at this moment, when so many of us are keeping ourselves isolated, missing the human connection we previously took for granted. Before the virus, we were already living in a world where loneliness was endemic, subject to impersonal forces that alienated us from each other. It can only worsen in the coming months. Prine, meanwhile, died of the very disease that has us further walling ourselves up. If he were here, he would likely be writing a painfully sweet song about it.