The music world lost a legend on 4/7, as the great singer/songwriter John Prine died of complications from COVID-19. Our own Holly Gleason explores what made him unforgettable, as an artist and a human being.

John Prine had a candy heart. Little kids, lunch ladies, German afternoons, forgotten old people, two-tone shoes, odd lots and tall tales. He didn’t just love it, he celebrated it.

As a songwriter’s songwriter, it was the tenderness and empathy that tempered tales of junkie vets blowing the welfare check to escape the trauma “while his kids ran around in other people’s clothes” (“Sam Stone”), a middle-aged single woman nobody wanted who deserves compassion (“The Oldest Baby In The World”), the fat girl and her boyfriend (“Donald & Lydia”) and the woman shipwrecked in a loveless marriage dreaming of a cowboy she’d loved in her youth (“Angel From Montgomery”). The pain was visceral, the details small. The folks we knew back home, many the kind we couldn’t get away from fast enough.

But not the Maywood, Illinois, daydreamer who became an Army mechanic, returned and got a job at the post office. He wrote songs because they were easier to play. His brother Dave had taught him guitar, and the sounds of the chords tickled him. Looking into the mailboxes, he wondered about the lives—and songs grew wings as he huddled in the shelters along his route.

The legend is easy. His pal Steve Goodman opened for Kris Kristofferson and said, “If you think I’m good, you should see my buddy.” They rolled into the Earl of Old Town as the chairs were going up on the tables; the owner saw a movie star, the girl he was dating and Goodman, and enough chairs hit the floor. After John played everything, Kris asked him to play them all again.

The next day, the two Chicago boys were on a plane to Nashville. They had record deals before they knew it. They were on their way, and what a way it was.

That first album had more career songs than most people get in an entire career. “Hello in There,” “Paradise,” “Spanish Pipedream,” “Sam Stone,” “Far From Me,” “Donald & Lydia,” “Six O’Clock News,” “Your Flag Decal Won’t Get You Into Heaven Anymore,” “Illegal Smile,” “Angel From Montgomery.” It was 1971, and threading the needle of social commentary with humor, basic blue-collar life with poetry seemed so easy. And for John it kinda was. He didn’t see the world like the rest of us. A little cockeyed, the connections he made and metaphors he saw were topsy-turvy.

Indelible images, where people are “naked as the eyes of a clown,” “down on the beach the sandman sleeps,” “old trees just grow stronger, old rivers get wilder every day,” freedom that felt like “a poster from an old rodeo,” “sweet songs never last too long on broken radios” or a red rose pressed “between a Holy Alphabet.”

The titles alone spoke encyclopedias: “Grandpa Was a Carpenter,” “Saddle in the Rain,” “Jesus: The Missing Years,” “Christmas in Prison,” “Come Back to Us Barbara Lewis Hare Krishna Beauregard,” “The Speed of the Sound of Loneliness,” “Egg & Daughter Nite, Lincoln Nebraska, 1967 (Crazy Bone),” “Iron Ore Betty,” “Unwed Fathers,” “Sabu Visits the Twin Cities Alone,” “Fish & Whistle,” “That’s the Way the World Goes ‘Round,” “You Got Gold,” “We Are the Lonely,” “Mexican Home,” “Summer’s End.”

And there’s the obvious stuff. The four Grammys. The Americana Lifetime Achievement Awards. The Songwriters Hall of Fame induction. The Mark Twain Prize. The first songwriter to read at the Library of Congress. He made records with Arif Mardin, Sam Phillips, Jim Rooney, Howie Epstein, Dan Auerbach—all music men of distinctly singular veins. He gave Bonnie Raitt her signature song, as well as providing Bette Midler’s Divine Miss M with its most poignant moments.

Even George Strait had a #1 country hit with “I Only Want to Dance With You.” He recorded a bluegrass album with Mac Wiseman and two albums of country duets with hard-country singers from Patty Loveless to Melba Montgomery, Emmylou Harris to Lucinda Williams, Margot Price, Kacey Musgraves, Iris Dement and his wife, Fiona Whelan Prine.

But really, he was more about the common man. Knew which meat-and-three had meatloaf on any given day of the week. Was known to sneak off fishing when he could. Liked to sneak into Barneys when he was in New York to bring his bride pretty new shoes. He made the best pork roast. He’d stay up all night playing guitars, cracking jokes and drinking Handsome Johnny's.

A road warrior, when he decided big record company life was not for him, he took his music to the people. After his best friend Steve Goodman started Red Pajamas, because no label would sign a guy battling leukemia, Prine decided to go that route too. The pair blazed DIY at a time when major labels were the mark of viability. Prine didn’t care. Heck, Prine passed up millions when offered, cracking his gum and saying, “But then I gotta talk to those people.”

Nah, John had other folks to talk to, other people to be important, too. If you’ve ever been to Wolf Trap, especially in the lean years when Oh Boy Records was mail-order mostly, you saw the ardor in the fans: sold out, pressed together, standing almost the entire show. Cheering, chanting, pressing the stage, it was like a holy-roller revival with a sweat-covered guy with a voice covered in cigarette ash unrolling the tapestries of the collected group.

Bob Dylan would cross a restaurant to say hello, Billy Bob Thornton would cast him in Sling Blade, Tom Petty would do a cameo in his video for “Picture Show” and Hunter S. Thompson would recommend Prine’s music to Bill Murray as a way to lift his spirits.

When his longtime manager, Al Bunetta, passed, Prine got the thing that’s probably the truest reflection of his Midwestern roots: he turned Oh Boy into a family business, installing son Jody Whelan Prine there and Fiona as his manager.

Jody knew how many young artists looked up the iconic songwriter. Suddenly Bon Iver's Justin Vernon, Jim James, Jason Isbell, Sturgill Simpson, Brandy Clark, Amanda Shires, Patty Griffin and more were among the cutting-edge songwriters who became part of Prine’s orbit. They energized him, fired him up, made him all frisky.

If later albums like Fair & Square took on the political and the sui generis of ordinary life, The Tree of Forgiveness was a masterwork that balanced his wry humor with straight-cut candor. “Caravan of Fools” took on today’s political morass, while “Summer’s End” offered a loving invitation to those struggling with addiction. And “I Have Met My Love Today” could only have been for his Irish bride.

That intimacy, that love beyond love. Prine beat cancer twice because of that love—his wife’s, his three black-headed boys, Jody, Jack and Tommy, and his mother-in-law’s pies. He’d talk about that when he was feeling grateful—and gratitude , like having fun, was something that Prine could do like no one else.

One thing’s for certain: John Prine led a singular life, savored every moment. Spent time in Ireland, where he had a home, and on the road where his fans were hi friends. It’s ironic the last song on Tree of Forgiveness was “When I Get to Heaven,” but we can only hope he truly is getting to enjoy every little thing he thought he saw.

Further reading: Down on the Beach the Sand Man Sleeps: Sweet Dreams, John Prine, Sweet Dreams