From his early days as a guitar-picking Army veteran at the dawn of the 1970s to a thriving Nashville career cut short by Covid in 2020, John Prine gave the world some of America’s best songwriting, from Angel From Montgomery to Dear Abby, In Spite of Ourselves and dozens more.

His insightful lyrics and gruff-yet-tender singing voice made instant fans of tastemakers including musician-actor Kris Kristofferson, who helped Mr. Prine find his first national audience.

Journalists, too, were drawn to the “Singing Mailman Who Delivers a Powerful Message in a Few Words,” read a Chicago Sun-Times headline for a 1970 article by film critic Roger Ebert, who caught Mr. Prine’s live act at a local club and became a lifelong friend as well as a fan.

Mr. Ebert’s piece is reprinted for the first time in more than 50 years as the lead story in music critic and Gazette contributor Holly Gleason’s new book, Prine on Prine: Interviews and Encounters with John Prine.

“Much of what’s in the book has been lost to the Internet,” Ms. Gleason told the Gazette by phone from Nashville, as she prepared for an appearance with Mr. Prine’s widow Fiona Whelan Prine and musician Lyle Lovett at the Rock and Roll Hall of Fame in Cleveland earlier this month.

Cameron Crowe, Robert Christgau, Dave Hoekstra and Pulitzer-winning oral historian Studs Terkel are among the other writers whose long-ago talks with Mr. Prine are collected in Ms. Gleason’s new book.

Book includes interviews done with John Prine that date back 50 years. — Slick Lawson

She also unearthed stories from Hot Rod magazine, Aquarian Weekly and now-defunct Pulse!, the music magazine of 20th-century Tower Records, along with a pair of Today Show interviews.

There’s even a People magazine profile by Cynthia Sanz that the magazine itself had forgotten existed, Ms. Gleason said.

“It spoke so much about the impact of this high-profile... artist on popular culture,” she said of the 1992 article.

Along with interviews, the new book includes an excerpt from actor-author Billy Bob Thornton’s screenplay Daddy and Them, featuring a character based on Mr. Prine, as well as a recipe for “the single greatest recipe for pork loin, ever,” said Ms. Gleason, a longtime member of Mr. Prine’s inner circle and one of the first female rock music critics to emerge in the U.S.

Stitched together with her own thoughtful introductions and essays, the collection will warm the hearts of Mr. Prine’s aficionados and engage the curiosity of others who have yet to discover his wide-ranging body of work.

“John contained multitudes,” Ms. Gleason said. “[He] had a candy heart, but it was kind of lopsided, which kept him from getting soft and treacly.”

Mr. Prine’s debut album, in 1971, brought forth the enduring Angel From Montgomery — a song so compelling it was almost immediately recorded by John Denver, Bonnie Koloc and Carly Simon — whose version went unreleased for more than 20 years — before earning its widest audience with Bonnie Raitt’s 1974 version. That album also includes Mr. Prine’s biting Vietnam ballad Sam Stone, the pot smoking ditty Illegal Smile and Hello In There, a tender song about the elderly.

“The new Dylan,” some called him in those early years — he was nominated for the Best New Artist Grammy Award in 1972 — but Mr. Prine was an original, made in no man’s mold. Instead of riding the magic carpet of stardom woven by multinational media corporations, Mr. Prine disembarked after a bare 10 years with “the majors” to start his own record company, a declaration of independence almost unheard of in the corporatized 1980s.

“John never wanted to make a record that couldn’t sit on the shelf with his other records. He had such high standards,” Ms. Gleason said.

Holly Gleason has had a long career as a writer and music critic, including for the Vineyard Gazette. — Allister Ann

Owning his own label, Mr. Prine couldn’t be forced to compromise and the gamble paid off, with two Grammy Awards and multiple nominations over the years.

Through two bouts of cancer, in the 1990s and the 2010s, Mr. Prine continued to create strong new work, including the acclaimed For Better, or Worse — a 2016 album of duets with female singers — and his final album, The Tree of Forgiveness, released in 2018.

“He proved that just because you’re in your fifth [career] decade doesn’t mean you get weaker.... If you’re really a student of your craft, your art and you really respect your talent and you’re not just dumping out songs because it’s time for a record, you learn a lot of lessons about your craft,” Ms. Gleason said.

While serious about his music, Mr. Prine had a fun-loving side, she said, recalling weekday poker games in the bridal suite at the Peabody Hotel in Memphis and tabletop bowling at the Prines’s Nashville home, by candlelight after a pork loin dinner.

“He was a zesty, funny guy [and] my hope for the book is that as people read it, they get a feel for who he was as a human being, and also listen to the music and... maybe love him a little more,” Ms. Gleason said.