John Prine is gone but the music is still going strong at his record label

It took a decade – the entirety of the 1970s, to be exact – for John Prine to discover he wasn’t cut out for the majors.

After releasing eight albums that showcased his plain-speaking and often wryly human brand of songcraft for two major record labels (Atlantic and Asylum), Prine set out to be his own boss. Along with manager Al Bunetta, he formed a label. It wasn’t a subsidiary venture of a major or a home industry that catered exclusively to his own work, but a company that viewed music-making as more than a hit driven, commercially motivated enterprise.

It was a mission only an artist who had been around the block with the major labels could implement. Prine was the artist and, with the 1981 release of a red vinyl holiday single that had him singing “I Saw Mommy Kissing Santa Claus” on one side and “Silver Bells” on the other, Oh Boy Records became the label. This year, Oh Boy and Prine’s lasting vision of what a record company should be, turn 40 years old.

“Looking back on it now, a lot has worked out,” said Jody Whelan, Oh Boy managing partner and Prine’s eldest son. “Some pretty significant risks were taken to start it. We weren’t exactly sure what the landscape would be. But as those risks kept working out, we were able to grow and keep the sort of ethos of why it was founded and work with music that wasn’t just John’s.

“When we started, Oh Boy was mail-order only. Then we got our stuff in the Ernest Tubb Record Shop in downtown Nashville. That was a big day. We slowly built our distribution to record stores. Now, for the last, gosh, 20 years, it has been operating as any major indie label would. But it was touch and go, especially in the early years.”

The history and “ethos” of Oh Boy Records will be detailed in a three-part online documentary series that will be streamed on YouTube this spring, summer and fall.

“I think a lot of labels say stuff like ‘artist first,’ but for us, what that means is that artists both own and control their artistic identity,” Whelan said. “We don’t look at having permanent ownership of an artist’s creative output. I don’t know how technical you want to get, but we don’t own someone’s masters (original recordings) or have a stake in their publishing. We would rather license it. We want to make sure any artist here never feels like it’s ‘us versus them.’ We’re all on the same team. Our goal is to have long-term relationships with folks and music that have something to say.”

For Prine, Oh Boy Records was the label that released two of his most important albums – 1991’s “The Missing Years” and 2018’s “The Tree of Forgiveness.” Both works reconnected the songwriter to longtime fans while introducing his music to new generations.

But celebrating the label’s 40th anniversary comes at a bittersweet time. Bunetta died in 2015 following a brief bout with cancer. Prine passed away just a over a year ago as one of the first and most prominent artistic losses to the COVID-19 outbreak. Whelan was brought on board following Bunetta’s death. Now, with a milestone anniversary at hand, both of Oh Boy’s founding voices are gone.

“With Al’s passing, we had to decide, as a family, what we wanted to do with Oh Boy. ‘Do we keep it going since we have other artists on the roster? Does John want to release new music?’ So we were having these internal discussions. After a few months, it became clear John didn’t want to work for anyone else. So we thought, ‘Can we do this in-house? Can we just have Oh Boy run by the family?’ So we decided we would give it a go. In some ways, it was a reset. There were a lot of people out there with decades of involvement in the music business whose experience didn’t translate well into the new era of streaming and social media. We weren’t as beholden to, ‘Well, this is how we did it in my day.’ That allowed us, I think, to move a little faster than some of John’s contemporaries when it came to adopting some of the new platforms and technologies.”

Best-known for ‘Paradise,’ John Prine was the uncommon Everyman

Adjusting to Prine’s passing was understandably and immeasurably more difficult.

“It was a shock,” Whelan said, “In some ways, it’s still a shock. But this has been a really hard year for a lot of people, so we’re sort of sharing in that grief. Half a million families – more, really – have dealt with COVID deaths.

“You know, a tornado hit Nashville in early March of 2020 and knocked out all of our power and internet at the office. Then COVID came and we shut the office down. We still haven’t reopened the office, so we’ve been working from home for 13 months now. It’s been a huge challenge, but we know we’re not alone. Also, the amount of support we’ve gotten over the last year has been incredible. There have certainly been days where that helps me get through – the outpouring of love and people playing John’s songs. A year later, we still feel that love.”

Of course, Oh Boy was and is by no means a vehicle for just Prine’s music. In fact, two of the label’s recent signees – Western Kentucky native Kelsey Waldon and Cincinnati area songsmith Arlo McKinley have maintained especially high visibility over the past year. Both have performed in Lexington during the pandemic when many artists have been forced off the road. Their success would have surely brought a grin to Prine’s face, just as Oh Boy undoubtedly did by allowing him to share the truest expression of his own music.

“John loved that he got to do things his way and could have fun with it,” Whelan said. “We always took the music seriously and the songs seriously. But the business part of it … John was adamant about not taking that seriously. We could poke fun at ourselves and just have a bit of lightness around everything.

“These days, I wear a lot of hats at Oh Boy. My official title is managing partner, although recently I have been chief lunch orderer. Depending on what the day is, I could be going to the store to get paper towels or negotiating a global licensing deal. But that’s the same as it is for anyone that runs a small business.

“We’re not putting out records to win awards or sell a million copies. Oh Boy puts them out because the music is really great and we believe in it. We want people to discover that music. I mean, John loved winning awards and selling records and all that, too, but that’s not why he did it. He did it because he loved performing for folks. He loved hearing great new songwriters. He just loved the community element of it all.”