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  • By Alan Richard


Updated: Oct 19, 2021

NASHVILLE — John Prine was tired of the hobnobbing the music business seemed to require. What mattered most to him was writing songs, singing them for people, and getting to know his followers and other musicians along the way.

Then he came up with an idea.

“We were riding in the car, and he said, ‘I think I’m going to start my own label in Nashville,’”recalled Jim Rooney, an accomplished music producer and close friend of Prine’s. “I said, ‘What are you gonna call it?’”

“Oh Boy,” Prine replied.

“I said, ‘What are you gonna call it?’”

More than 40 years after that exchange, Oh Boy Records survives.

Not only would Prine, who tragically died in 2020 from complications from COVID-19, release many a great album on the label. He'd also sign other offbeat and promising roots-music artists that would push music in new directions even today.

“That’s how the record label started,” said Jody Whelan, the managing partner of Oh Boy Records, said at a discussion at AmericanaFest held in celebration of the label's anniversary. “It’s about supporting the songwriting and the process.”

Fans were so drawn to Prine, they'd been known to send Prine a check for $10 as a down payment on his next album even before it would be released, Whelan said.

“The community John built wasn’t about the next album and ‘What are the hits?’” he said. “He also loved bringing young artists out and taking a real interest in the next generation… in ways that were fun and real.”

“With a lot of help, we’ve been able to keep that going.”

At AmericanaFest, writer and musician Peter Cooper of the Country Music Hall of Fame and Museum filled in as the session host when writer Holly Gleason couldn’t attend.

Joining the discussion were Jim Rooney, Whelan and talented young singer-songwriters Tre’ Burt and Kelsey Waldon, both following in Prine’s enormous footsteps on Oh Boy Records.

From left, Peter Cooper, Jody Whelan, Tre' Burt and Kelsey Waldon at AmericanaFest.

Cooper noted that the conversation was happening on Friday, Sept. 24 — 50 years to the day after Atlantic Records released John Prine, the singer-songwriter’s debut album.

Prine's first record became one of the most influential singer-songwriter recordings of all time, dazzling many in Nashville's songwriter community almost from the start. The record was produced by the masterful Arif Mardin, and the cover shows a blue jean-clad Prine sitting on a haystack.

“He used to say, ‘I’m from Chicago. What do I know about a haystack?’” Cooper said.

“In fairness, they didn’t always know what to do with him,” Whelan said.

Gaining independence

Prine started Oh Boy with his partner and manager, the late Al Bunetta, and Dan Einstein, 10 years after the release of his debut album.

He likely got the idea for his label own from friend Steve Goodman, the singer-songwriter best known for “City of New Orleans” (recorded by Prine, Willie Nelson, Johnny Cash and others).

Goodman had terminal cancer and couldn’t wait for a new record deal, so he released an album on his own Red Pajamas label instead, Rooney said.

Oh Boy is remembering Prine and reflecting its own legacy with a new documentary film. The label has released two of the film’s three segments. The final segment comes out in late October.

The label also just released Broken Hearts & Dirty Windows, Vol. 2, a tribute album to Prine to raise money for the Hello in There Foundation, created by the Prine family. The album features striking versions of Prine’s songs by many friends and admirers, including Emmylou Harris, Brandi Carlile (who sings the last song Prine recorded, “I Remember Everything”), Bonnie Raitt, Jason Isbell, Amanda Shires and others.

(Story continues after the videos below.)

Arrival in Music City

Prine first came to Nashville to record an album with producer Cowboy Jack Clement, Rooney said. The project never quite came together. Later, he decided to make the move permanently.

“Steve (Goodman) ended up taking over (production duties for) Bruised Orange, but that got John to Nashville. He really loved it,” Rooney said.

Prine would become good friends with songwriter Roger Cook (“Long Cool Woman in a Black Dress,” “I'd Like to Teach the World to Sing”) his bass player Rachel, whom he’d marry, and others.

“He ended up in this community of songwriters,” Rooney said.

After Prine moved to Music City, Prine and Rooney had their choice of studios where they could play and record. Clement had built Jack Clement Studios, which would become Sound Emporium. He also had a studio in his home in the Belmont neighborhood and Jack's Tracks, later purchased by producer and songwriter Allen Reynolds.

“We could go anywhere, any day and record some of those songs,” Rooney recalled.

Producer Jim Rooney

The first recording on the Oh Boy label was a 7-inch single of “I Saw Mommy Kissing Santa Claus” and “Silver Bells.”

“That one we recorded in July for Christmas and put it out on red vinyl,” Rooney said. (For those who don’t know, Prine was nuts about the holidays. “He loved Christmas and kept up a Christmas tree year-round,” Whelan said.)

Jack Clement Studios was one of the “great places to play, and (the musicians) could play all together, and the singer could sing with the players and we didn’t do any kind of (tracking),” Rooney said.

“I like a room full of musicians and a really great singer who can stand up there and give them something to respond to,” said Rooney, who'd use the same approach on great records by Nanci Griffith, Iris DeMent and the late Hal Ketchum. “And we had a lot of fun doing it.”

That's how Prine made German Afternoons, Rooney said, the 1986 album featuring the terrific “Speed of the Sound of Loneliness.” The album would be nominated for a Grammy Award.

Prine also worked with producer Howie Epstein of Tom Petty and the Heartbreakers on The Missing Years and other albums, but kept coming back to traditional country players and classics from the country music songbook.

Having his own label before it was common for many big names in roots music gave Prine the freedom to create.

Cooper remembered talking with Prine on the airplane from Los Angeles back to Nashville after he'd won a Grammy for 2005's rootsy Fair & Square, in the Best Contemporary Folk Album category (whatever that is).

“Dude, you beat Springsteen!” Cooper recalled telling Prine.

“No, we beat Columbia,” Prine replied with a smile.

Unique talents

Along the way, Prine and Oh Boy Records began to sign other artists — sometimes obscure ones, such as R.B. Morris from Knoxville. Prine makes for a good duet partner on "Roy,"from Morris' album Take That Ride.

Prine also would sign one-of-a-kind folk musician Dan Reeder, who made his own elaborate instruments, to a lifetime contract.

“It was about the songs and about the quirk,” Cooper said.

The brilliant, eccentric East Nashville troubadour songwriter Todd Snider also was part of the Oh Boy family, the label helping launch the recording career of one of the city’s most interesting musical personalities.

“John loved hanging out with Todd and singing,” Whelan said.

Along the way, Rooney and Prine would talk endlessly about old country songs and play them for one another. “He was always singing songs to himself” and humming, Rooney said, “songs of all kinds, and we shared a love of old country music — and he knew it all.”

Prine never stopped discovering old country songs and began to tinker with the idea of recording a series of classic country duets. “He started making a list of other female artists he’d like to seek a song with," Rooney recalled.

One candidate was the distinctive singer-songwriter Iris DeMent. “He immediately understood her,” Rooney said.

Then Prine asked other country legends to join him, including Melba Montgomery and Connie Smith. The result was 1999's In Spite of Ourselves, one of Prine's best.

It was a great creative period for Prine.

“Then in the middle of this, he got his cancer diagnosis,” Rooney said.

Prine endured massive neck surgery and didn't know if he would sing again, but ultimately would recover to make some of his best albums and inspire more songwriters yet to come.

“He was just an extraordinary person in his terms of his ability to relate to people in a very deep, sympathetic way,” Rooney said. “He was always looking out and listening and looking.”

Prine loved the album he made with bluegrass great Mac Wiseman, 2007’s Songs for Average People, Whelan said.

Some years later, he recorded another splendid album of country duets, 2016's For Better, Or Worse, featuring veterans such as DeMent, Alison Krauss and Kathy Mattea and younger artists such as Miranda Lambert, Kacey Musgraves and Amanda Shires.

Cooper asked Rooney at the AmericanaFest session: Just how do you produce John Prine?

“Oh, you just shut up,” Rooney said.

Prine's final album, the warm, funny and wonderful Tree of Forgiveness, was produced in Nashville by Dave Cobb and features some of that next generation who worshipped Prine and ended up becoming friends, including Jason Isbell, Shires and Brandi Carlile. The album won album of the year at the Americana Music Awards, and the record and its songs would be nominated for three Grammys.

After the success of Tree of Forgiveness, Prine traveled back to Memphis, where he'd recorded his 1979 album Pink Cadillac with Sam Phillips' son, Knox, and Sam himself.

He re-recorded one of the best cuts from that album, “How Lucky,” for Amazon with producer-engineer Matt Ross-Spang. Prine enjoyed working with the young producer so much, he gave him a Cadillac.

Appropriately, Prine was honored posthumously in 2020 with the Lifetime Achievement Award and two Grammy Awards for his final single while living, “I Remember Everything.”

“I don’t think I’ve ever met anyone as deep as he was… as far as caring about other people,” Rooney added. “And that showed up in his songs.”

Wellspring of talent

Turning to the younger artists on the panel at AmericanaFest, Cooper asked how much they'd known about Prine and his long journey in music when they agreed to join the Oh Boy Records family.

“Kelsey and Tre', were y’all aware of this?” Cooper asked.

“I was aware of the history, and that’s of course one reason why of course why I was so attracted to Oh Boy,” Waldon said.

Even before she knew Prine, Waldon would see him in the Melrose neighborhood and at Prine’s favorite meat-and-three spot, Arnold’s.

Prine and Kelsey Waldon before they played the Grand Ole Opry together.

“I just not could believe you would see John Prine hanging around,” said Waldon, noting that she’s from rural Ballard County in western Kentucky where Prine’s parents were born.

After signing to Oh Boy, Waldon sang two duets with Prine on the EP The Kentucky Sessions. Waldon was about to meet up with Prine for some show in Europe when the elder singer had to return to Nashville, where he'd succumb to the effects of the virus.

“Just having a relationship with John, especially in the later years of his life,” Waldon said. “Just watching his shows live, too. I’ve never seen a happier person on stage. He was just like, lit — living his best life on those tours.”

Prine's generosity and interest in younger artists — and his wife, Fiona's grace and the family's dedication to the Oh Boy label — have inspired Waldon's approach to making music.

During the pandemic, Waldon released an outstanding EP of cover songs, They'll Never Keep Us Down, and invited friends and Nashville artists of color Kyshona, Adia Victoria, Devon Gilfillian and others to join for passionate takes on songs by Nina Simone, Neil Young, Kris Kristofferson and others.

Waldon also covers Prine's own “Sam Stone” poignantly on the album.

“He talked (a lot) about community,” Waldon said. "What John and Fiona have given to me, it’s made me want to give things to other people.”

Tre' Burt remembers Prine mainly for the music. During Prine's final illness, the young songwriter visited his bedside.

“Most of my relationship with John until last February... was through music,” he said. “So when John was in the hospital… it felt very natural, the only way to try to connect with him was by song.”

Burt seems to draw his vocal inspiration from Prine and Bob Dylan for his vocal inspiration, but his lyrics are deeply original, dreamlike at times and sometimes speaking to the experience of young Black men in America.

“Dixie Red” is Burt's tribute to Prine. Featuring Waldon on accompanying vocals, the song appears on his record You, Yeah, You, released on Aug. 27 of this year:

Blue smoke from my cigarette

danced upon my eye

Moon has risen and it lit your way

to paradise

“I found John a little bit later in my first and only year of college,” said Burt, recalling how he'd visit his friend Kevin's house, smoke a little, and listen to Prine. “It kind of blew my mind.”

“In each song is lessons,” he said. “Difficult lessons that aren’t meant to be understood immediately.”

“I’ve been starting all my shows with ‘The Late John Garfield Blues,'" Burt continued. "I’m not sure what it means.”

Burt also joins Waldon for a song about Prine on her forthcoming album in spring 2022.

Tre' Burt's latest album.

At AmericanaFest, Waldon and others spoke of their grief over Prine's passing even as they continued their work.

While not nearly as painful for Prine's family, Waldon recalled her own sadness.

“Actually, I couldn’t really listen to the music, either — his older voice," she said. "It still kind of makes me sad sometimes, but a lot of it makes me really happy, too."

“I cherish those memories (of Prine) so much, and it really taught me a lot, too,” she said. "That life, it’s all just so short.”

“I actually drank a lot, too,” after Prine's death, Waldon volunteered, adding that she could mark 10 months of sobriety around the time of AmericanaFest. “One day I woke up and was finally kind of able to write about it.”

At the recent AmericanaFest conference session, a man from the audience spoke up, saying that on the day Prine passed away, he'd texted a friend: “My Elvis died.”

“That’s the way I felt,” the man said.

“Yeah,” Weldon replied. “That’s how much his music meant to everybody.”

“I understand.”

MORE: Our feature profile of Kelsey Waldon after Prine's passing and the release of They'll Never Keep Us Down, and our profile of Nashville singer-songwriter and author Marshall Chapman and her stories from a long journey in music--including her final visit with Prine.

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