Music journalist Holly Gleason enjoyed a longstanding relationship with John Prine. Gleason grew up on Prine, in fact, before she became an observer as a music journalist and confidante as a friend (and, at one point, his publicist). She often traveled with Prine on tours in the late 1980s and represented him in the 2000s.

It was only natural, then, that she’d take on the task of assembling the collection of intriguing and eclectic pieces — some from publications long gone — that make up Prine on Prine: Interviews and Encounters with John Prine, released Sept. 12 by Chicago Review Press.

Gleason’s work has appeared in publications and media sites like Rolling Stone, the Los Angeles Times, the New York Times, the Oxford American and NPR Music, and she is the editor of Women Walk the Line: How the Women in Country Music Changed Our Lives (2002) and a co-author of Miranda Lambert’s New York Times bestseller, Y’All Eat Yet?, released in April.

Gleason took time to speak with Texas Music about her latest project.

Why Prine?
Who better? A great American songwriter, a wonderful, quirky, impossibly decent, once-in-a-lifetime kind of human. The way he lived his life is so inspiring — and those songs say everything about the callousness of the world, and how we can be better, more compassionate people. He wanted to show, not tell, the circumstances that the unseen find themselves in, and he sure did.

Courtesy CBS News

What criteria did you use for the material you selected? Give us a sense of how this all came together?
Some pieces were critical — the Roger Ebert review, for example. Other than that, the idea was to find pieces that demonstrated the man Prine was in each of the phases of his career, so you could see him find his path as a man who wasn’t interested in what major labels were selling … someone who could really lock into who he was.

Part of the process was also looking for things that weren’t just another profile. I was blessed, because Dan Einstein, his longtime co-manager and the guy who really did the work to set up and build Oh Boy Records, said if I did Prine on Prine, he’d help me.

We used to talk about how the image that emerged of John, as he became this Americana icon, missed all the best parts of who he was. It also missed the work he put in to create a label, making music on his terms — whether the classic Jim Rooney albums or the rock stuff with Howie Epstein — when artists would sooner die than not be on a major label. It changed the game, but John insisted on making his music on his terms.

Some days, I’d go by the bakery that Dan and his wife Ellen had opened after Dan left the music business, just to get a treat, and he’d say, “You know, we gotta find that Aquarian Weekly piece.” Or “John really loved that Country Song Round-Up story. Don’t you know the old editor?” Mind you, Country Song Round-Up had been closed almost 30 years, but I did know the editor. I called, and Rick Bolson went down to his basement and found the issue and sent me pictures of the pages.

When I had a hard time getting the writer of a Hot Rod editor’s letter to give me his permission, Dan picked up the phone and called him. He said, “Dave, if you don’t get Holly the release, you’re out of the book.”

And again, so many of these publications aren’t just out of business … they’re long gone. I was blessed that George Dassinger, the publicist I’d recommended for Prine’s The Missing Years and Lost Dogs + Mixed Blessings, kept such meticulous files. He had Gil Asakawa’s Tower Records’ Pulse piece in pristine condition, as well as an actual copy of Prine’s People profile. For perspective, when we reached out for permission, their licensing department had no idea the piece existed or how to find it; we had to send them a scan of it.

It was hours of transcribing TV shows, radio interviews, the night at the Library of Congress with U.S. Poet Laureate Ted Kooser. Stuff like that. But in writing it all down, the heart emerged.

It was also beautiful connecting with the people who’ve contributed, because I got to hear their John Prine stories, to get their sense of who he was in that moment, what the world was like when they talked to him. And we pulled from some places people wouldn’t have expected, whether it was that freewheeling Bobby Bare Show that used to air on TNN, or John’s mom talking about the hash she used to send with him back to Nashville.

The other thing was how generous people were: John Mellencamp and Randy Hoffman allowed us to use his PEN Award presentation speech; Billy Bob Thornton helped us get permission to use John’s big monologue from Daddy & Them; Robert Hilburn got me copies of the files of his pieces from the L.A. County Library when I couldn’t access them.

It was that kind of detective trip, with a really great soundtrack.

Of course, I had to accept that in many cases, with venture funds and billionaires buying media companies, many of the licenses would’ve been too expensive to include. One publication wanted $1,500 for a short piece. That would have been an impossible chunk of the advance. I was lucky many of the writers were freelancers who owned their stories and could grant me permission.

You knew John well. What did you learn about him during the project you didn’t know before?
I don’t think I realized how unthinkable it was what Dan, John and Al Bunetta were trying to do. They had this laughing-as-they-went sense of “we’ll figure it out.”

Watching those Today pieces Mike Leonard did — back when music wasn’t part of the morning show menu, let alone a guy who’d yet to win a Grammy or had a certified hit and fled the majors — it hit me. They were all working hard against a massive machine to do something devoted to one artist who wanted to be his own man. It was unheard of.

It’s very Midwestern, that idea of work hard, work for your family. But watching all that develop, remembering when major chains didn’t want to deal with a bunch of individual accounts, when you weren’t taken seriously if you did it on your own and didn’t have the power of Warner Brothers or A&M Records behind you. John didn’t care. Seeing the commitment, the work and the not-flinching in retrospect? It really is impressive.

And it spoke very profoundly to those values that defined John.

Why is Prine so beloved?
Integrity. People saw a man who not only walked it, he didn’t talk about it. He was a man who just did what he intended … wrote songs that spoke for people no one would listen to — and got people to pay attention.

“The Oldest Baby In The World,” which he wrote with his buddy “Funky” Donnie Fritts, has an empathy for a gal well past her prime but a heart that would be a gift to anyone. That lyric … “with her hair so unnaturally curled” … you could see some 48-, 55-year-old barfly in her lycra just hoping. And the chorus closes, “Let’s rock that old baby to sleep,” because he believed she deserved love.

Who wouldn’t love a man who saw the world through those kind of eyes? And for as sharp an eye as he had on the world around him — and he read multiple newspapers a day, listened to NPR and the news shows — he kept that childlike wonder. He just loved making people happy, making them laugh, knowing when meatloaf was on the menu at the Meat and Threes in Nashville, keeping a Christmas tree up all year long or buying his wife shoes when he was on the road. Simple stuff — it just lit him up.

Original hand-drawn portrait by Paul King (, used here with permission of the artist

What distinguished his songwriting from others?
His sense of detail, his empathy, his real tenderness to people who were ignored and voiceless. Look at the characters: Donald, Lydia, the middle-aged housewife in “Angel from Montgomery,” the young girl being shipped off in “Unwed Fathers,” Sam Stone, the elderly couple in “Hello in There,” James Lewis in “Six O’Clock News,” Billy the bum, Barbara Lewis Hare Krisha Beauregard, even Jesus during his missing years.

When John sings about those people, they’re given this almost glow. He doesn’t remove what makes the world disdain them, but you realize how wrong the world — or the people — can be for casting them off. I won’t say listening to John will make you grow some compassion, but I’d be surprised if you didn’t slow down and smile at these kinds of people after you listen to a few of these songs.

Even “Grandpa Was A Carpenter.” What a celebration and portrait of a man out of time. You can see everything, know exactly who this man was “who voted for Eisenhower ’cause Lincoln won the war.” So happy, so fun, so engaging.

And he could use that to suck you in, then lay some big truth on you. “Your Flag Decal Won’t Get You Into Heaven Anymore” was all about the bravado and empty showmanship of representational patriotism. If that isn’t as right now as anything out there, what is? When he was bashing onstage, it was fun, but he knew.

And he also knew how to interject great lines! “That’s the Way the World Goes ’Round” with its “naked as the eyes of a clown”? Is there a truer or more lovely way to describe being stripped to the bone?

I could go on and on. All the songs, the lines, the devices. And John would just smile and go, “Oh, Holly! It’s just a song.” He worked damn hard on those songs, and he had high standards. But that wasn’t the point. He didn’t want to pomp around telling you about his awesomeness; he wanted you to feel or see something and pass the best possible emotion on to the next people you encountered.

You and I have been Prine fans back to the ‘70s when he wrote some of his best songs. But during the latter part of his career, say the “last wave,” he appeared to gain a new level of popularity — beyond the folkies. Is that accurate? And if so, what do you attribute that to?
Well, that’s why this book, because that’s maybe how it seemed once the internet took hold. But the reality is John always had a strong audience, was selling out Wolf Trap and Red Rocks, playing great venues. He wasn’t hungry for acclaim or press attention; he wanted to write songs he was proud of, he wanted to play for the people who wanted to hear it.

More than “beyond the folkies,” John had always resonated with smart rock fans, Vietnam veterans, veterans of later wars, activists, rural people. But because he wasn’t Paris Hilton, people in the media maybe didn’t realize. And if you’re not in the press … especially to New York and L.A. … you don’t exist.

That said, once they did the first Broken Hearts & Dirty Windows tribute project, the younger acts who loved him came forward — and their fans discovered him. When you added social media, the Kacey Musgraves, Sturgill Simpsons, Jason Isbells exponentiated their love among all the people who love their music. I mean, who doesn’t think Kacey singing “Burn One With John Prine” to John Prine is the sweetest moment in Americana history?

Do you have favorite Prine memories?
They’re so small, but pungent. When he recorded the first live record in San Juan Capistrano, we all went out for dinner after — and Harry Dean Stanton tagged along. Or maybe Harry Dean was the ringleader. But we were all sitting around this table in this stucco walled upstairs room,  bathed in the glow of candles. Harry Dean sang Mexican songs, they told jokes, and it was just this intimate, completely musical moment for nothing except the songs and the joy of being together.

Once, we were leaving a venue in England, and the dressing room was on the third floor. It was cold and damp, and there was a railing going down these pretty steep steps. I was bringing up the back end, but John turned around to make sure I was coming — and he had that naughty grin, like “C’mon.” He was carrying his good black coat over his shoulder, was chewing his gum, and in his arms, he had his cowboy boots. Sticking out of the shaft of one of the boots was a mostly full bottle of Aqua Velva. That was quintessentially John.

But maybe my favorite is John showing me that fabulous Victrola jukebox that Steve Goodman had given him for “You Never Even Called Me By Name.” It was a secret then that John was the co-writer. He made me promise never to tell, then told me the story of how, trapped with only an AM radio in West Virginia, they’d listened to so much country radio they’d gone sideways. So they started writing lines on the wall, “And when we woke up, I told Stevie, ‘If you take the blame, you can have the song.’” John told me that, then he laughed. Was he concerned about the money he lost? “No, Holly. Look at this jukebox!”

What about a favorite Prine song?
Im very partial to “Souvenirs,” used to write it all over my schoolbooks growing up. That couplet: “Broken hearts and dirty windows make life difficult to see / That’s why last night and this morning always look the same to me” just felt like everything to a kid from a high-impact home, so in love with life and so utterly disappointed over and over again.

“Storm Windows” was the most amazing roux of this profoundly sad melody, the way winter doesn’t just feel but lays all over the Midwest like a case of dysthymia covered with a wet down quilt. And again, his metaphors and pictures! “A country band that plays for keeps”? It really did sound like an old beer joint or tavern song. But then that idea: “Down on the beach, the sandman sleeps” told me a lot about the man who came for my sleepy head, as well as the idea that “silence is golden ’til it screams.” In a high-impact house, it was like someone cracked the roof in half and looked down.

Beyond that, the hush of “Mexican Home.” Dear heavens! That line about the lightning burning the sky like alcohol? You know exactly what the air felt like that night … And if you settle yourself, you realize: John’s writing about his father’s death. It was a sudden thing; he died before John’s debut came out, there on the front porch. You take that in, and you just … well, there are no words, only awe.

But my first musical epiphany was hearing Bonnie Raitt late one night on WMMS long after I was supposed to be asleep. There was a blue glow from the 8-track player/portable radio, and the air wasn’t moving. I was hanging off the end of my bed, upside down and on my back when Bonnie’s voice flowed out of the radio with such authority and loneliness.

We were Catholic, so I didn’t know what a witness was. But that’s what that performance was. This woman, so emptied out by being tethered to a man who was empty by the time he got home. He had nothing for her, just sat at the table eating his food silent, leaving her to clean up the dishes and stare into the night, wondering how it got like this.

My family had terrible rows, or said not much of anything. I used to look at the sky, wishing when the people on that spaceship told me not to play with that latch, I’d have listened. “Angel from Montgomery” told me there was no spaceship, no one from another galaxy coming back to get me. The two emotionally shipwrecked people in my house weren’t special, and I was very definitely going to have to survive and thrive here.

Maybe it’s why I didn’t get married. I always wondered about where that rodeo cowboy got off to … if he thought about that “Angel” in her kitchen, getting chapped hands. And long before I knew who Sam Shepard was, I understood how you could be somewhere utterly detached and unfulfilled and still wistfully remember when there was a glimmer of something far more alive.

Like John, I guess, I never wanted to lose my independence.