Oh Boy Records: John Prine’s Family Affair

The Oh Boy Records team hold down the fort at the label's Germantown offices. (L-R) Jody Whelan, Collin Fidler, and Eileen Tilson. Photo: Travis Commeau
The Oh Boy Records team hold down the fort at the label's Germantown offices. (L-R) Jody Whelan, Collin Fidler, and Eileen Tilson. Photo: Travis Commeau

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Random generosity occasionally falls from the sky. Explain Hank or Dylan. Explain John Prine. These artists, and many others, of course, bring words to the ground for everyone — often providing gifts in the form of ideas ahead of their time. Prine’s presence in the world particularly burnishes some of its rougher edges. From the moment Kris Kristofferson found him at Chicago’s Quiet Knight pub, he has done good works.

His self-titled release on Atlantic in 1971 is a gleaming blade that cuts through the years into today, and his current and acclaimed album The Tree of Forgiveness states again plainly that real living is for the everyman. And, fittingly this recording resides on Oh Boy Records, Prine’s own and Nashville’s oldest active independent label.

Founded in 1981 with longtime manager Al Bunetta, Oh Boy Records was one of those gifts ahead of its time. Prine was three records into a contract with Asylum, and he knew it wasn’t right. No major label would be right. When his contract was up, he and Bunetta agreed there was a better way. Maybe.


There was some precedent. Prine’s good friend, Steve Goodman, who had penned the mythic “City of New Orleans,” had worked with Bunetta to set up his own Red Pajamas label. They had engaged Dan Einstein (now the owner of East Nashville’s Sweet 16th Bakery) on the business side of things, as would Prine and Bunetta for Oh Boy.

“I had [starting Oh Boy] in the back of my head,” Prine says, from a train as he tours Europe in support of Tree of Forgiveness. “I saw it working with Steve. I didn’t really want to talk to the majors anymore [after Asylum]. I didn’t think they had a grasp on what I was doing. I knew I had a really good core audience. And I just wanted to service them for a while. It’s where I was and what I wanted to do before I went to a major label.

“The first thing we put out was a Christmas red vinyl 45 with ‘I Saw Mommy Kissing Santa Claus.’ The only place you could buy it was at the Ernest Tubb record store on Lower Broadway. The rest of them were through mail order. The word got around that I was going to do an album — this was before the internet — and people started sending me money . . . they trusted me, you know. It was a form of social media through the U.S. mail. We knew we had a solid audience, and they really showed up in spades.”

Oh Boy was born.

Photo: Travis Commeau
Photo: Travis Commeau

“We had no real idea,” he says. “We just forged ahead. We didn’t really care, you know. I knew my living was on the road. I could be in control of when I would take a break. It wasn’t something against the major labels. I wasn’t walking around in that frame of mind, nothing like that. It was stressful and frustrating for me. I didn’t see any reason to go and take a big advance check from them — and then owe them all these records to pay off my debt. I wanted to remove the stress.”

For the record, “Silver Bells” was on the B-side of that red Christmas 45. The first Oh Boy album release was Prine’s Aimless Love in 1984. And they were improbably crowdfunded before crowdfunding was a thing.

“I could not have started Oh Boy Records without Al,” Prine says. “Al had helped Stevie set up Red Pajamas so he knew what we needed to do. And, I think taking Dan Einstein on board was one of the best things we did for the label. Dan really had a great grasp of the industry and knew exactly how to run the day-to-day operation.

“Between them they knew a lot of people — Al was a natural-born storyteller and I know that helped spread the word about us and what we were trying to do. When Dan left it took Al a while to find someone to replace him, and when he did it took two people to do the job he had done. I’ll always be grateful to both of them for what they put into Oh Boy.”

Wait. Natural-born storyteller teams with natural-born storyteller to run an independent label in a town that has frowned often on independence? Prine, Bunetta, and Einstein were proving there was room for free thinking.

“They had both developed a following — John a larger following, Steve [with Red Pajamas] more of a cult following,” Einstein says today. “But they were both very loyal followings, same kind of nature where people would come out year after year and see them play. The thought was well before independent labels were in vogue or wasn’t really a thing. It was growing in a couple of areas. Rap had started that, and there were certain areas where it already had a foothold.”

Prine’s oldest son, Jody Whelan, is Oh Boy’s current director of operations and understands the spark that has carried them all through 37 years.

“Well, I guess to go backwards, John has always put himself in a position to be lucky,” Whelan says, from Oh Boy’s office. “Right? You know, not many people get a confirmation early from Roger Ebert [who broke an unknown Prine in the Chicago Sun-Times] and Kristofferson. That happened because he was part of the community. Because of his friendship with Steve Goodman. Because people around him wanted him to succeed.

“I think that’s the same thing in the ’80s when they started Oh Boy. He had taken care of the audience and the fans. They were sending him money. It’s the same feeling now that he’s got his first record of original material out in 13 years, and people are sort of tripping over themselves to help him — the whole independent music community in Nashville and so many friends. There aren’t many people as well-liked as John. I think everyone is seeing that there’s an actual benefit to not being an asshole.”


This is the blood flow. The label actually represents hope. Whether the invisible songwriter living in a backhouse off Eastland, or the singer living in the backhouse inside his or her own head, Oh Boy provides a shining light. You are not alone. Prine’s wife and present-day manager, Fiona, expands on the heart of Oh Boy’s family ways and community sense as they travel. Following Bunetta’s sudden passing in 2015, the Prines had to look to one another.

“It really is a family-run business, and even though it is kind of organic in a way, we had to look at it as if we were starting over,” she says. “We just started going piece by piece through each part of John’s career. There was the record company, the publishing, the merchandising, the road, and publicity — and then the day-today management of the bigger opportunities. And we also recognize the legacy piece as being something that was becoming more and more relevant that needed a lot of attention. We are who we are. As Jody likes to put it very well, ‘We’re a nimble little organization.’

“We all have our hands in everything. I mean it’s true to say that Jody is completely responsible for the day-to-day running of the record label and has really grabbed that with two hands — especially in the area of our growth in the digital world. So that’s been really gratifying, to watch him just get in there and learn everything.”

This nimble little organization is today riding the crest of a wave created by Prine’s newest and fastest-selling record. Oh Boy is the physical manifestation of his recording career, one that earned a Grammy for the 1991 album The Missing Years, and a second for Fair & Square from 2005. He joined the Nashville Songwriters Hall of Fame in 2003, the same year he was awarded a Lifetime Achievement Award by the Americana Music Association. The Grammy Hall of Fame in 2015 finally inducted that 1971 self-titled debut album, which gave listeners 13 jewels, including “Sam Stone,” “Hello in There,” “Paradise,” and “Angel From Montgomery.” He accepted the PEN New England’s Song Lyrics of Literary Excellence Award in 2016, and at the age of 70, Prine was named Artist of the Year by the Americana Music Association in 2017 (an honor he’s up for again this year).

But Oh Boy is also the physical manifestation of a life well lived. See Whelan’s reference to the benefits of not being an asshole. Nashville has embraced Prine from the moment he arrived in town for a weekend visit in 1973 — falling in then with songwriter Lee Clayton. They knocked on the backstage door at the Ryman on a Friday night, and he quickly found himself standing behind the curtain of the Opry in a narrow passage, wedged between Ernest Tubb, Roy Acuff, and Bill Monroe. He and Clayton went from there to Hank Cochran’s houseboat in the wee hours. Enough said. His Nashville papers have been in order ever since.

“It’s been another one of those redefining things that we’ve discovered,” Fiona Prine says. “The number of friends and allies that we’ve found over the years. Nashville absolutely stepped up to the plate when they saw us take over the business. We had nothing but support and help. I think John would echo all of that — the community has been hugely helpful.”

Whelan takes it a step further.

“Hopefully, [what we’re doing is] about the culture, and about the storytelling and being able to raise that up,” he says. “That’s where it can be harder to see from the outside, but once you’re in it and you see it, whether it’s the organizations, or just the friendships, or the shows and the players, it feels really natural. It’s a part of the community. I don’t think that could happen in another town.”

Elaborating on the importance of the label’s relationships, he points to Nashville-based marketing, distribution, and management company Thirty Tigers.

“That was one of the first things we started working on after we took over,” Whelan says. “We had kind of a patchwork distribution, worldwide, both physical and digital. It really made sense to consolidate that into one company that we trusted and respected. Also, one that we knew we could lean on. It was in town, and it’s been great, because we can just go over there and talk with them whenever we want and bounce ideas around. They do things like radio promotion where — we could hire an outside person in — but they’ve already represented Jason [Isbell], too. When they make that call, it’s just as powerful, or more so, as if we were trying to call. It builds our network and relationships. I think, again, it’s like every business — 90 percent of it is the relationships, and just 10 percent of it is your own knowledge.”

East Side resident Eileen Tilson, Oh Boy’s director of marketing, was brought on as the Prines restructured. A Music Row veteran, Tilson had stepped away from the business, but found a friendship with Fiona through work at Thistle Farms, the non-profit organization that provides employment and housing support for women survivors of trafficking, prostitution, and addiction. Her long-held wish to work for an independent label meant she couldn’t say no when approached to join Oh Boy.


“I did find myself thinking, ‘Oh, I’m getting back into the music industry — but it’s with John Prine and Oh Boy Records,’” she says. “You can’t really say no to that. I feel incredibly lucky to be at an independent label, something I’ve always wanted, and being in a place that is a family-run business is also sort of a sweet spot. It allows you a lot of flexibility, allows you to be creative. I love it. There isn’t a day that goes by that I don’t feel really, really lucky.”

Tilson also adds further insight into the label’s place in space and time.

“When we stepped into Oh Boy, there was shifting going on in the independent community,” she says. “John Allen had very recently stepped in [as president] at New West. Concord [Music Group] had very recently got Rounder and had a new vision for that. Dualtone was doing things. So it was. Then here we are with this label that has had, I think such an extraordinary history, but was relatively unknown.

“It kind of gave me freedom to say: ‘You can tell this story and we can do it justice.’ It’s how we present this and build on this community — show the world that Nashville has a really strong independent community. Nashville’s always been seen for its major labels — major country star labels, and Music Row. But this whole side of independent communities never had a national identity. To me, I think that that was a cool piece of it to say: ‘Yeah, we can show this, we can do this.’”

It is true that Oh Boy has managed to survive, even flourish, and fly under the radar simultaneously. While Prine’s initial vision was ahead of its time, there was the ability to navigate rough waters in the early years, thanks largely to Bunetta and Einstein.

“I think the answer [to its survival] is found in both sides of that coin,” Einstein says. “What Oh Boy has meant to Nashville, and what Nashville has meant to Oh Boy. Certainly, it speaks to a lot of artists, even though you might not be on a major label or even an independent label.

“The connection with people, once you make that connection, it’s indelible. So there was always an optimism. The label always projected optimism, which is a can-do spirit … John Prine embodied that, and embodies it still.

“Nashville, to Oh Boy, was a community that accepted us. ‘You guys are for real. You’ve made records and you’re selling some numbers.’ There was at least an understanding and a value to great songwriting. It was appreciated and recognized. We operated in sort of this parallel universe, but it was still a mutual respect.”

Oh Boy’s roster has included Prine, Kristofferson, Slick Ballinger, Shawn Camp, R.B. Morris, Riders in the Sky, Donnie Fritts, The bis-quits, Dan Reeder, and Todd Snider over the years. Prine and Reeder are the two active Oh Boy artists today. The label has also released a dozen reissues of classic country music artists, including compilations like Oh Boy Classics Presents Country Greats, featuring Merle Haggard, Roy Acuff, Don Gibson, Willie Nelson, and others.

And, in a songwriters’ town, songwriters have always been acutely aware of the label’s presence.

Snider considers his work with Oh Boy to have been defining in his life.


“They took me into their family, and I felt they showed me how to do the best I could,” he says. “I feel like they were altruistic people who took good care of me just to do it. They took over for my third record — and if anything they taught me how to work with other people and how to listen to other people, and not be as much of a right fighter as I think I was when I was young.

“It wasn’t coming from a label that wanted me to be a pop star. It was coming from a songwriter that knew I wanted to be a lifer. It’s as hard to be Guy Clark as it is to be George Jones. To this day, when he meets a singer that he sees something in, he really helps out. They were people that walked me through those years that most of my peers talk about as having been so hard. When I was around John, I just wanted to learn more about songs and try to get as good as I could at that . . . it’s a cool thing they’ve built over there. When I look back on it, I still feel part of it in a way.

“Oh Boy is important to Nashville. It’s been fun to watch . . . I feel like this town is really going through a high-art phase — and in my opinion, I would say that John’s the epicenter of it. He’s the Hank Williams that people moved here to be.”

Tilson agrees that Oh Boy respects the song. “I like to think that we will always be a home to people who don’t necessarily fit in a genre,” she says. “I think that Oh Boy strives to always represent good music, whatever that looks like. We strive to put a voice behind someone who has something to say. That feels really genuine, feels like it’s in line with the John Prine vision.”

Collin Fidler, the label’s e-commerce manager (and another East Nashvillian), points further to a symbiotic relationship within the community.

“I think it feels like John Prine is a Nashville success and vice versa,” he says. “Everyone’s cheering us on at Oh Boy and in the same sense, if we’re working with someone, many Nashville musicians, we’re giving them work — they might be opening for John — and it will show. John Prine succeeding means Nashville is succeeding.”

Again, it is important to celebrate hope in this town. The impact Oh Boy has had on Nashville’s independent artists over four decades is hard to quantify in numbers. It should be viewed more in terms of hunger and dreams, and celebrated for its sanctuary. From that moment Prine knew he could no longer walk the major-label walk, musicians everywhere have benefitted. Oh Boy is an idea ahead of its time, one that has given for almost 40 years.

“I think in seeing someone like John, a singer-songwriter can believe in doing things their own way,” Whelan says. “People have always seen he’s honest and authentic. I think it gives someone the license to think that they can do that for themselves, too, whether Oh Boy’s involved in it or not. I think that it’s the idea that you can see someone you respect doing it, and that makes it seem doable.”

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