Oh Boy! John Prine’s Family Business Is Booming Like Never Before

Margo Price and John Prine perform during the 2017 Newport Folk Festival at Fort Adams State Park on July 30, 2017 in Newport, Rhode Island.
Taylor Hill / WireImage – Margo Price and John Prine perform during the 2017 Newport Folk Festival at Fort Adams State Park on July 30, 2017 in Newport, Rhode Island.

John Prine has a secret. Before leaving for England to headline the Cambridge Folk Festival, he knows in less than 19 hours he’s going to walk out onstage at the Newport Folk Festival as Margo Price’s unannounced special guest to sing “In Spite of Ourselves.” The frisky romp, originally recorded with Iris DeMent, celebrates the odd, sometimes cranky way love endures between grown-ups.

For the 71-year-old former mailman from Maywood, Ill., there’s nothing to be cranky about these days. Following the 2015 death of his longtime manager Al Bunetta, the three-time Grammy winner turned his fiercely independent Oh Boy Records into an actual family business. With wife Fiona Whelan Prine at the helm as manager, the man responsible for the iconic classics “Sam Stone,” “Hello In There,” “Blow Up Your TV,” “Paradise” and “Angel from Montgomery” released 2016’s Grammy-nominated For Better Or Worse, a redux of In Spite of Ourselves featuring duets with various female country and roots luminaries including Lucinda Williams, Emmylou Harris, Patty Loveless and DeMent.
Son Jody Whelan took over day-to-day operations of Oh Boy Records, but even more importantly, he started introducing Prine to a new wave of writer/artists who viewed the legendary songwriter as a prime influence. Jason Isbell, Sturgill Simpson, Kacey Musgraves, Bon Iver, Margo Price, Dan Auerbach all clamored to write, record and tour with the man entering his fifth decade as a legendary American artist.
Just as importantly, Prine’s creative output only grew stronger with the heightened attention. The Tree of Forgiveness, released this spring, is outperforming any Prine title to date with critical accolades from Rolling Stone to Pitchfork and more pouring in. Beyond physical sales, his streaming numbers are such that when Spotify erected billboards all over Nashville, the Americana Artist of the Year was one of them.

“They see John as a contemporary artist,” explains Whelan. “Not just a heritage act, but someone whose music is current.”
He’s also been hitting the road, bringing his masterful short stories of slightly off-kilter people to audiences hungry for songs that look like the rest of us. Some of his recent tour numbers according to Pollstar Boxoffice include nearly $295,330 grossed at the Filene Center at Wolf Trap in Vienna, Va., June 1; and $210,352 grossed at Louisville Palace Theatre on June 8.
Reveling in his patented gentle compassion and quirky details, Prine just announced a New Year’s Eve stand at Nashville’s Ryman Auditorium, as well as a run of dates in Mississippi in December.
Iris DeMent and John Prine
AP Photo / Mark Zaleski – Iris DeMent and John Prine
Iris DeMent and John Prine perform during the Americana Honors & Awards Show at Ryman Auditorium in Nashville Sept. 13.
Pollstar: It’s been an amazing year for you with the new album, the touring. Does any of this surprise you?
John Prine: Day by day, I am. I look around, think about all the stuff that’s happening – this far into a career – and I’m amazed. The response to this record has been crazy. I’ve never had one react like this, and it makes me feel like people do want new music.
When we spoke before the record came out, you said, “It’s hard, because I’ve got all these albums with good songs on ’em. If I’m going to do new music, it needs to be better than the songs I’m not getting to play already” – those are some pretty tough standards.
Well, I think that’s important. You want to grow and move forward. I think people who love the music deserve that, and I never want to fall short.
And you’re playing a lot of these new songs – always a risky proposition when people are coming for ‘Sam Stone’ and ‘Your Flag Decal Won’t Get You Into Heaven Anymore’ – at your shows.
I’m doing every song on (The Tree of Forgiveness) every night. Some of the songs you’re talking about, the ones people expect, too, but nobody’s screaming for this one or that one, which is nice. We do “Angel from Montgomery,” “Hello in There,” “Sam Stone.” We’ve been doing “Dear Abby” and “Illegal Smile.” We’ve got a great version of “Ain’t Hurtin’ Nobody” with the band. And I’m doing “Bruised Orange,” which we haven’t done in a while, so people who come for the older songs seem pretty happy.
And the new ones?
It’s funny. People are coming to the shows with their CDs already. They’re singing all the answer stuff back to me, and they have been since almost right before the record came out. It’s crazy. I thought it was the band at first, then I looked around, and realized it was the crowd.
That’s funny.
It’s great! When I sing that song “Crazy Bone,” they’re all over it!  Pat McLaughlin, who’s in the band and co-writes with me every week, he played it out at a writers in the round (in Nashville) before we cut the song. He called me up, and said, “Man, the crowd jumped on that song like barracudas. They were singing it back…”So right from the get-go, some of these songs were connecting.
Beyond more to pick from, do these songs have any impact on the older ones? 
It makes the older songs sound better (laughs). The ones we’ve played tens of thousands of times, mixing them up with the new songs really changes things up. It gives them new energy, and lets them breathe in different ways.
After all you’ve done, can I ask what runs through your veins or goes through your head before you go on?
I’m less nervous than I used to be, but I do like to have a little edge. I don’t wanna just casually stroll out there.
Are you playing any part of the show just you and your guitar?
Oh, yeah. Every night, I change it around. The band I have to keep on set list, but when I do my part, I switch ’em up all the time. You never know what I might sing when I’m out there by myself!
It sounds like you’re really having a ball.
I’m really enjoying going out and playing these new songs. I’m doing three times as much touring as I’ve ever done, and it’s just great. The shows are full. The bands we’re playing with are great. We keep looking over at each other every night onstage, going, “Is this really as good as we think it is?” The only thing I don’t like is the getting there.
What do you mean?
For some reason, traveling is even worse than it was 50 years ago.
Are you busing?
Fiona and I took a bus in the spring and early summer, up in Kentucky and Indiana. We got reminded we can’t sleep on a bus. Some people are lucky, and they can. But the thing about busses: they’ve gotten nicer looking, but that’s about it. The Interstate roads are just terrible, and you bounce around so bad.
And air travel? 
It’s what we do a lot. But, well, anyone who’s been on a plane, needing to get somewhere, knows what I mean.
John Prine
Denise Truscello – John Prine
Pearl Concert Theater, Las Vegas, Nev.
In a perfect world, how would you do it?
I’d like a train if that made sense. We’re gonna take a lot more trains in Europe for sure. But if it was really what I wanted, I’d like really nice cars of my own to drive, and enough time to get there. Check into a nice hotel, have a great dinner and then do the show the next night after soaking up the city. It’d cost a fortune to do, but you said “In a perfect world…”
You’ve also had some pretty great opening acts.
You’re not kidding! I sit down with Fiona and we have this pool of talent who’ll come out and play with us. I found out some of them play for not nearly as much (money) as they’d get on their own, but they like working with us… and we love working with them.  We’ve had Margo out, Sturgill, Jason, his wife Amanda Shires on her own. We had the Milk Carton Kids recently. I knew I liked their music and their humor, but just playing with them was great. I loved listening to them, and the stuff we play together is terrific. We do “That’s The Way The World Goes ‘Round,” and it’d tickle you. And we’re going to the Northwest with Todd Snider, going to the Portland Theater and Eugene. It’s always fun having Todd out.
Anyone else?
Tyler Childers was great.  We had Langhorne Slim in Pittsburgh. Colter Wall’s done a few shows. When he opens his voice to talk, you don’t expect that voice to come out! And Amanda Shires is gonna do some more dates. She takes chances, and bigger chances than most do with their music. I love that about her.
And you’ve kind of taken chances, too. Checking into a hotel for a week to finish the songs, working with Dave Cobb and cutting live every day without a lot of pre-production. Pulling songs from the past, from co-writing for Dan Auerbach’s album, from wherever your songs come from. 
Fiona knows me better than anyone. She knows I work best in hotel rooms, so she sent me off to the Omni. It was great. I met some awesome people in the bar, I could get a good pork chop when I was hungry, and I got the record done. Dave Cobb was terrific. He produces a lot of people I know, made records I love. That he didn’t want to hear the songs until the day we cut them might seem risky, but he understood what we were doing so well, I just trusted him.
And it worked.
It feels like there’s good luck dust all over it. I’ve had good records before, but none of it has been like this.  And that’s great, because every penny we’re making goes right back to the family. Every bit of it is for the grandbabies.
Family is a big piece of this for you, isn’t it?
It sure is, and everyone’s doing great. I was meeting with Jody last night, talking about the future of my label. It seems a little crazy: the future of my label. But they’re doing such a great job.
To have all of this music, and to be finding all these new audiences and collaborators, then to be able to pass it down to the grandkids? That makes me feel really good about all of this.
And to think “Grandpa Was A Carpenter”…
And their Grandpa is a folk singer.

Prine Movers 
When John Prine established Oh Boy Records in 1983, he wanted to be free to make his music the way he heard it. Following in the footsteps of best friend Steve Goodman, who’d formed his own label when his leukemia kept people from signing him, Prine engaged managers Al Bunetta and Dan Einstein to figure out sales, distribution, production and never looked back.
With the passing of Bunetta, Fiona Prine, his wife, stepped into a true management role – and quickly assessed the landscape. The woman, who’d run U2’s Windmill Studios in Dublin, has a keen mind for business. Beyond advising Prine on large frame issues, she moved to consolidate the business in the hands of the people closest to the iconic songwriter.
Enlisting Prine’s son Jody Whelan, who’d been running a company in a completely different industry, he brought his business sense to Oh Boy and began assessing the strengths of the catalogue, the artist and his impact. The Operations Manager has not only increased the focus on social media, streaming and catalogue development, he also began reaching out to younger artists who’d been influenced by Prine. The cross-pollination and modernization of delivery systems has welcomed a new generations of fans.
Eileen Tilson, who’s built a diverse resume working at various major labels, as well as being involved with Zac Brown Band’s Southern Ground, met Fiona through Nashville charity Thistle Farms. Recognizing a diamond in any setting, she brought the marketing and promotion force into Oh Boy to maximize the label’s reach.
Under their steering, Prine’s Spotify numbers alone have quadrupled. The Tree of Forgiveness sold over 50,000 pieces street week, making a career high No. 5 debut on the Top 200, plus No. 1 on Billboard’s Americana Album chart. It also landed at on the Country, Indie and Rock Album charts, showing the breadth of appeal.
And finally, longtime tour manager Mitchell Drosin is now serving as Prine’s agent. Having worked the dates for years, Drosin knows the venues, the realities of markets and most importantly, how to make the most of a John Prine show. Between Drosin and Fiona, they’re consistently creating interesting packages, headlining Wolf Trap, Red Rocks, the Ryman and various festivals around the world.
As Whelan says of his father, “Working wth the next generation has never felt cheesy to John. … seeing how the new world works, and seeing how the young artists work really energizes him.”
John Prine
John Kurc – John Prine
Hidden Treasures: Prine Jewels Beyond The Classics
Everyone knows John Prine’s “Hello In There,” “Sam Stone,” “Donald & Lydia,” “Blow Up Your TV,” “Angel From Montgomery,” even the George Strait No. 1 “I Only Want to Dance With You.”  But only the real connoisseurs know beyond the standards, where songs get even richer, sweeter, deeper and – on occasion – raucous as heck..
“Blue Umbrella”
The Singing Mailman Delivers (demo) 
Sweet Revenge Prescience about an impending heartbreak.
“Bad Boy”
German Afternoons
A lament from the kind of man you should never fall for.
“Late John Garfield Blues”
Diamond in the Rough
Country-tinged social commentary without preaching.
“Some Humans Ain’t Human”
Fair & Square
Gorgeous acoustic lament that indicts modern politicians, lobbyists and real estate developers with irony and small details.
“Saddle In The Rain”
Common Sense
Aggressive, funky and almost accusatory. Live, a foment that snakes and whirls.
“Christmas In Prison”/ ”Silent Night All Day Long”
A John Prine Christmas
Off-kilter Christmas carols.
“Oldest Baby in the World”
Aimless Love
A hushed lullaby to the middle age barfly who just needs a little tenderness.

“Sabu Visits The Twin Cities Alone”
Bruised Orange
A wry take on promotional duties from a man who would ultimately start his own label before DIY was a thing.

“Mental Cruelty” with Kacey Musgraves

For Better, Or Worse
Sparklng, crisp country from Prine’s second female duets project.“Down By The Side”

Pink Cadillac
Destitution painted in vivid details, B-3 clouds and soul “woo” chorus rising.“We Are The Lonely”

Lost Dogs & Mixed Blessings

A lockstep anthem of the alienated, isolated and out of sorts. Blistering guitar.
“Jesus, The Missing Years”
The Missing Years
A talking blues considering where Jesus went – and what he did – during those unaccounted for years.

“When I Get To Heaven”

Tree of Forgiveness
Spoken blues weaves into a big strummy chorus celebrating a heaven with cocktails of vodka and gingerale, a cigarette nine miles long and too much fun.

“Take A Look At My Heart”

The Missing Years
John Mellencamp co-write that churns a warning to the ex-girlfriend’s next victim.

“Back Street Affair”  with Patty Loveless

In Spite of Ourselves
Hard country throwdown that twists on how wrong and right it can be.

“Unwed Fathers”

Aimless Love

A stunning portrait of a pregnant girl sent away alone to have her baby.

“Storm Windows”

Storm Windows
A benediction for long winters and paralyzing loneliness: “Down the beach, the sand man sleeps/ Time don’t fly, it bounds and leaps.”

“She’s My Everything”
Fair & Square
A love song that says it all.