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Award-Winning Author & Music Critic Holly Gleason Traces The American Songwriting Legend’s Life Through the Media, Cookbooks, Films, Hot Rod Magazines & the Library of Congress



Nashville, TN: When Holly Gleason met John Prine at 20, she had no idea the man who’d written “Angel from Montgomery,” “Hello in There” and “Sam Stone” would be a major player in her life’s journey. The young music critic stringing for The Miami Herald spent two hours on the phone, took a job, saw her story spiked – and forged an alliance lasted for the rest of the Songwriters and Grammy Hall of Famer’s  life.

On Sept. 12, Chicago Review Press releases PRINE ON PRINE: Interviews & Encounters, part of their Writers in Their Own Words series. Edited by Gleason, this is a labor of love. Following musicians through various phases of their careers via appearances in the media and other places, PRINE ON PRINE collects work from noted mediacrats Studs Terkel, Roger Ebert, Cameron Crowe, Robert Hilburn, then Poet Laureate Ted Kooser, Robert Christgau, Dave Hoekstra, Ronni Lundy and Grammy-winner Bob Mehr.

Along the way, Prine runs away with a writer from Hot Rod, graces the cover of No Depression, takes a bespoke role in Billy Bob Thornton’s “Daddy & Them,” receives the Pen Literary Award for Lyrical Achievement from John Mellencamp, is profiled in PEOPLE, twice on NBC’s “Today” by Emmy winner Mike Leonard and shares a couple favorite recipes and stories in Shuck Bean, Stack Cake & Honest Fried Chicken. Record company bios, Chicago folk history, stories around starting labels and cooking dinner, publications long gone and a throwdown with Bobby Bare are all part of the fun.

“John was many things,” marvels Gleason. “It is so easy to see him as this elder Americana legend, writing songs that transcend time and place to touch your heart or soul or life. But he was also a fun guy, with a clear vision, a deep love of home and all it stands for and an absolute sense of self that allowed the tenderness of how he saw the world to remain pretty consistent throughout the book.

“Social commentary without preaching, his a sense of right and wrong informed how he lived. Whether it’s Robert Hilburn seeing him in the hilarious limbo of life without a major label, Dave Hoekstra celebrating the Earl of Old Town’s anniversary, as well as Steve Goodman and the folk movement that birthed both men or Chris Willman delving into women’s reproductive autonomy for a charity single of ‘Unwed Fathers’ with  Margo Price, Prine’s aim was true.”

Gleason is the former fiancée of Oh Boy, Red Pajamas and Blue Plate Music co-founder and Prine co-manager Dan Einstein. She spent many of her formative years as a nationally recognized music critic in Prine’s world, which provides empiric insight into many of these pieces from being there. Gleason later provided media strategy and services for In Spite of Ourselves and Fair & Square, remaining friends with the Grammy-winning legend throughout his life.

PRINE ON PRINE is as much about capturing an artist creating something that hadn’t really been done, tracing the arc from unthinkable to commonplace. It would not be nearly the book it is without the help of Dan Einstein, who passed away as the book was nearing completion. But he got on the phone, made calls and helped find some of the pieces here, which might have been lost forever based on what it took to track down some of them. Even the cover picture – from a photo session for PEOPLE – was basically forgotten.”

Having created, edited and contributed to Woman, Walk The Line, the 2018 Belmont Book Award winning collection of essays about how female country artists profoundly impact individual lives with contributions from Taylor Swift, New York Times best-selling author Alice Randall, Rosanne Cash, Grammy-winning historian Holly George-Warren, poet Caroline Randall Williams, top James Beard Award winner Ronni Lundy, food activist Ali Berlow and more, Gleason understands curating a narrative can sometimes reach places a single reported narrative can’t. That was the goal for PRINE ON PRINE, and across myriad mediums, moments and conversations, a sense of the man across his truly lived life emerges.


Early Praise for PRINE ON PRINE: Interviews & Encounters

“As close to an autobiography as we’re going to get from John Prine, Prine On Prine captures the inimitable, whimsical voice of one of our greatest songwriters, from the beginning of his career to his final days, evolving from the shy, self-effacing, uncertain youngster film critic Roger Ebert discovered to the wise, cunning veteran who left a body of work probably second only to Dylan. Nashville legend Holly Gleason knew the man and assembled this brilliant collection with a knowing eye and loving heart.”

Joel Selvin, Here Comes The Night: The Dark Soul of Bert Berns and the Dirty Business of Rhythm +   Blues; Fare The Well: The Final Chapter of the Grateful Dead’s Long Strange Trip

“Listening to John Prine instantly jolts me to a higher vibration and feels like I’m walking on holy ground, free, fearless and naked as the eyes of a clown. He shakes me, wakes me, conjuring up emotions I didn’t know I had, reminding me that tenderness is a virtue. His words make me want to be a better person, to recognize myself in everyone’s eyes, to hold all of humanity in high esteem – because we’re all in it together.  

“Praise be to Holly Gleason for this oh so important, exquisitely curated collection. John Prine improved the world by being alive. Let’s do our best keep that big, beautiful ball rolling.”

Pamela Des Barres, I’m With The Band and Lets Spend The Night Together

“The brilliant genius of John Prine was not only the magic he had in writing  about everyday life for everyday people; but just as important was that his lyrics provoked you into thinking about everyday things that you may never have given much thought to and after he woke up those feelings, you realized you couldn’t have said it any better. The respect, admiration and love for Prine and his songs that Holly Gleason has is obvious not only in her eloquent introduction, but in the interviews she selected to pay proper homage to him.”

Linda Moran, President & CEO, Songwriters Hall Of Fame

Nobody wrote songs like John Prine, filled with humor, humanity, and perfectly cock-eyed detail. But what this elegantly curated collection—culled from interviews, TV and radio appearances, and even recipes—reveals is that…well, that’s just who the guy was. Whether he’s at the Library of Congress or in the pages of Hot Rod magazine, Prine’s wit and fierce independence constantly shine through.

 —Alan Light, The Holy or the Broken: Leonard Cohen, Jeff Buckley &the Unlikely Ascent of “Hallelujah”

I’ve loved John Prine since I was a little girl. PRINE ON PRINE makes me feel like he’s been talking to me since he was a young man, and seeing him go through the phases of  his career is a real gift. Holly Gleason knew John, so she understood how to take these interviews, movie scripts, tv shows and recipes and create a sense of who he was when he got done writing or performing. Now even more than a legend, he feels like a favorite uncle.”  

Miranda Lambert

“With a deep understanding and knowledge of John Prine – the man and his music – Holly Gleason has searched every nook and cranny to curate a thoughtful biography of one of our greatest singer-songwriters. Her insightful text sets the scene as we experience Prine, the unfiltered raconteur, via five decades of media coverage, from major magazines to niche publications, television scripts to a recipe book, talk show appearances, movie roles and his PEN Award presentation. Prine on Prine is both revelatory and entertaining.”

Holly George-Warren, Janis: Her Life & Music and A Man Called Destruction: The Life & Music of Alex Chilton

“Reality can involve a lot of imagination, and no one was better at imagining and painting real pictures about people you felt you knew.  I enjoyed getting to know John more through Holly’s curation and writing.  A true master.”

Eric Church

“This book is a stunner! Only the glorious Holly Gleason could assemble such a magnificent collection to celebrate the life and world-changing artistry of her friend John Prine. Perhaps the most joyful history book you’ll ever read. His music explodes from the pages.

Tom DeSavia, Under the Big Black Sun: A Personal History of LA Punk  and More Fun In The New World: The Unmaking and Legacy of LA Punk

Holly Gleason is an author, journalist and academic whose work regularly appeared in Rolling Stone, Los Angeles Times, Musician, Variety, Oxford American, Playboy, Interview and Miami Herald. Serving as HITS Nashville Editor and a Pollstar Sr. Contributing Editor, the Rock & Roll Hall of Fame/Case Western Reserve Fellow is the 2019 Country Music Association Media Achievement Award winner, creator/contributor of the 2018 Belmont Book Award-winning Woman Walk The Line: How The Women of Country Music Changed Our Life, co-author of Miranda Lambert’s New York Times best-seller Y’All Eat Yet: Welcome to the Pretty B*tchin Kitchen and Prine on Prine: Interviews & Encounters, published by Chicago Review Press Sept. 2023. Nominated for five Southern California Media Awards, including Entertainment Journalist of the Year and Music Criticism, her Library of Congress essay on Tammy Wynette’s “Stand By Your Man” is up for Entertainment Commentary and her POLLSTAR cover story on Dolly Parton is competing for Entertainment News Feature. She lives in Nashville, TN.

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