The "we" was Prine and his then-manager, the now-deceased Al Bunetta, who steered Oh Boy through its improbable early years, when the company was established without an official business plan, solely as a vehicle to service new product to Prine's existing fan base and enable him to make money from touring. He put out a lone Christmas single that first year, waited three years to release a full album, then started receiving checks in the mail from fans who wanted to pre-order the next one. Much like a Kickstarter campaign, the deposits came in large enough volumes that his follow-up album was funded before he had even written the material.
Forgiveness, the second Prine album released since Bunetta's death in 2015, represents Oh Boy's increasingly modern approach to labeldom. Prine's wife, Oh Boy managing partner Fiona Whelan Prine, convinced their son, Jody Whelan, to help out short term during the transition, but he quickly became director of operations. Eileen Tilson brought a digital marketing background when she was hired as director of marketing and promotion. Whelon, who was schooled in the restaurant business, brought a fresh outlook to the record industry, asked the right questions and helped Oh Boy adopt a digital strategy on top of its historic -- and still viable -- mail-order approach.
"It was good timing," says Whelon of his crash course in music economics. "Everything has changed so much in the last five years. I think some people were holding on to important and good knowledge and historical information, but maybe not stuff that's as relevant going forward. If everyone's learning about streaming and new ways to promote online, maybe it helped me not to have the [old-school] baggage."
By owning his label through the decades, Prine kept a bigger chunk of his sales revenue as an artist and funded his own career longevity. He was able to hone his singular writing style -- using conversational phrases to convey layers of meaning with a subtle, sometimes biting wit -- without bowing to a traditional label's market-driven guidance. Prine now stands as an icon in the Americana genre, which will hold its annual conference in Nashville Sept. 11-16. He hopes to repeat as the Americana artist of the year, and he'll be presented BMI's troubadour award on Sept. 10 in a private dinner. That award celebrates his songwriting, but Oh Boy has become iconic in its own way.
"I'm really proud of it," says Prine. "As time's gone by and people starting independent record companies has kind of become the thing, it's great that we've stayed afloat for this many years."
Extending the label's longevity has become a major undertaking for the Oh Boy team. They convinced Prine to become more involved in social media, helping to expose him to a younger audience. Tilson points with pride to his 75,000 Instagram followers, all collected in the last three years. "There isn't another artist among John's contemporaries that has an active Instagram audience like we do," she says, and many of those followers are next-generation fans who have discovered him in recent years.
"The majority of John's career was sort of an older 55- to 64-year-old demo, and now we're saying it's not quite 50/50," notes Tilson. "But you're definitely seeing those tried-and-true fans and their children and their grandchildren coming to the shows."
Once those younger fans are won over, they naturally extend Prine's legacy since they'll outlast the first generation of believers.
"We see streaming as a way of telling John's story decades from now when there's no more CD players left in the car and iTunes is gone away," says Whelon. "About half of John's listeners on Spotify are under the age of 34. If we can get someone to come to a show, listen to an album, hear the lyrics, we're confident we've made a lifelong fan, so if we can get 30-year-olds listening to his music now, this is something we can keep doing."
Oh Boy also has singer-songwriter Dan Reeder's fourth album on the way, and its catalog includes scattered titles by Kris Kristofferson, Todd Snider and Donnie Fritts. But with the label's new-era focus, it's interested in expanding judiciously. Adhering to Oh Boy's original intent, a new signee would need to be an artist-writer who has a definable point of view. While Whelan would oversee the rollout, Prine definitely approves.
"Certainly with the first signing," says Whelon Prine, "I think there is value there in having John supporting that artist -- you know, 'John Prine signed me to my first record deal.' He's actively excited about the idea of endorsing a couple of young songwriters."
By eschewing a traditional label deal more than 35 years ago, Prine chose an unusual path that's now a little more usual. Such companies as Thirty Tigers allow artists to own and control their masters, and hip-hop acts like Chance the Rapper have been able to work outside of the majors to find their path. Oh Boy continues to embrace that independent spirit, putting itself in position to perhaps be part of another remarkable -- even unintended -- development.
"Chance is doing things that Kendrick Lamar and other people at his level are doing, but people don't see him as, 'Wow, he's independent, so he's missing out,' " notes Whelan. "I'm hoping eventually that will be true in country music, too. It's getting closer. You're going to see someone who has like a Chris Stapleton story, but on an independent label."