For someone whose father loved Christmas so much that he kept a Christmas tree up year-round, Jody Whelan has only recently started to subscribe to the idea that you don't need a traditional milestone as an excuse for a celebration.

"I don't know if I'm getting older, or if COVID is doing this to my brain, or if I'm becoming more sentimental, but [I'm realizing] we don't have to wait 50 years to celebrate something, or it's okay to celebrate something in its 51st year," says Whelan, the oldest son of John Prine and the director of operations at his record label, Oh Boy Records. "Maybe there's not as much of a press hook ... [but] if you're proud of something, it's okay to talk about that in year 41 or year 39-and-a-half."

"It sort of falls under, like, it's okay to eat cake for breakfast," interjects Fiona Whelan Prine, the late folk legend's wife and Oh Boy's president, as her son laughs beside her.

"It wasn't that every day was Christmas to John — it was that every day held the same kind of magic that Christmas holds for many," Whelan Prine continues. "What other guy do you know that went to see the Rockettes and cried when Santa came onstage?"

Prine — who would have celebrated the 50th anniversary of his self-titled debt album on Sept. 23, the 40th anniversary of his record label, Oh Boy Records, this year, and his 75th birthday on Sunday (Oct. 10) — spent nearly 50 years imbuing his music with that magic. That's not to say his songs are full of light and happiness, though some certainly are; rather, it means that even at their darkest and saddest, there's a sparkle to Prine's lyrics. He was empathetic but honest, and funny but wise.

"Some people describe it as self-deprecating, but I don't even know if it's that," says Whelan Prine. "I think John lived in a very unique little corner of the world, in his own head, and his own life amazed him ... He was bemused and sometimes bewildered by his life."

Broken Hearts and Dirty Windows Vol 2 John Prine tribute album
Oh Boy Records

Perhaps most telling of Prine's talent is how his words hold up when performed by others, as on the new tribute album, Broken Hearts & Dirty Windows: Songs of John Prine, Vol. 2, out Friday (Oct. 8). The record finds a dozen close friends and collaborators, from Iris DeMent and Emmylou Harris to Valerie June and Nathaniel Rateliff & the Night Sweats, adding their own shimmer to Prine classics, some deep cuts and even his final recorded song.

Broken Hearts & Dirty Windows, Vol. 2 arrives more than a decade after Vol. 1, released in 2010. "That was always one of, I thought, the coolest things Oh Boy put out," says Whelan, who, along with his mother, assumed their positions at the record label in 2015, after the death of Al Bunetta, Prine's longtime manager, with whom the artist co-founded the label in 1981.

Future volumes of Broken Hearts & Dirty Windows were always the plan — "I have notebooks where I'm like, 'What if we asked this person to do that [song]?' Whelan says — but Prine's final album, 2018's The Tree of Forgiveness, and other projects took precedence. Even after Prine died of COVID-19 in April of 2020 — the early days of this ongoing pandemic — it took nearly another year to start the plan in motion.

The Recording Academy enlisted Brandi Carlile to honor Prine, a Grammy Lifetime Achievement Award winner in 2020, with a performance at the 2021 Grammy Awards in March, and she and her team asked his family for their input on which song she should perform. It was only a couple weeks out from the all-genre awards show when they settled on "I Remember Everything," the last song Prine recorded, which was released shortly after his death; they were short on time, but Whelan, Whelan Prine and the rest of the label decided to ask Carlile to record her version of the song so they could use the moment to (finally) announce Broken Hearts & Dirty Windows, Vol. 2.

"It made it seem that we were geniuses," Whelan says, "but it really came together [at the last minute]."

Once they put the word out about the project, Prine's family found they had more willing participants than would fit on a single record. "I could see that growing to Vol. 4 very easily," Whelan Prine says; replies Whelan, "Five feels safe."

"After five might be reaching," he adds, "but then, by the time you get to number six, there's gonna be new singer-songwriters, the next generation. So maybe it only stops when people stop buying it, I don't know."

They're not being bombastic. "We didn't just learn this after John passed, but we were certainly really becoming aware that John's music has crossed all genres," Whelan Prine says. "There's bluegrass, there's traditional country, there's country-pop, there's straight-on folk."

"There's genres I actually didn't even know about until someone tagged us," Whelan adds, "like, 'Hey, I didn't a synthwave version of this.'"

DeMent, Harris and Bonnie Raitt — whose new version of "Angel From Montgomery" is more plainspoken and like Prine's than her 1974 recording of the song — were pals and peers of Prine's for decades, but the nine other artists on Broken Hearts & Dirty Windows, Vol. 2 are more current collaborators and friends. Many were early in their careers or not well-known nationally, or not even making music yet, when Vol. 1 was released.

"In the last five years, in particular, before he passed, Jody and I were not shy about letting people meet John and tell him how they felt about him," Whelan Prine says. They enlisted new opening acts for Prine's shows, including Tyler Childers and Margo Price; Carlile, Jason Isbell and Amanda Shires — all featured on Vol. 2 — played and sang background vocals on The Tree of Forgiveness.

"Once we reached out to them ... we all very quickly became part of the greater music community that we call Americana," Whelan Prine continues. "John left us ... so much, including a community, an amazing community, of people."

In 2019, Oh Boy Records signed its first new artist in 15 years, Kelsey Waldon, then quickly followed by signing Tre Burt and Arlo McKinley — all artists Prine personally approved of. Emily Scott Robinson joined the label earlier this year, and will release her Oh Boy debut in late October; Prine had died before she signed, but, says Whelan Prine, "I know he approves."

Prine's family now has the dual role of carrying on not only his record label but his legacy as an artist. Their plans for a week's worth of tributes and celebrations marking 2021's big milestones for both Oh Boy and Prine have been postponed to October of 2022 due to the COVID-19 Delta variant — a decision they made, Whelan says, by using the same question that guides all of their choices: What would John have thought?

"As a man and as an artist, I think he had a lot of integrity — as a performer, too," says Whelan Prine. "We know what the end goal is, and we know what our guardrails are. So, we are transparent, we're honest, we try to do good work -- I use a big G, big W with that ... and we try to honor the legacy that John left, not just to us, but to the world. And we feel the music is important, we feel the song's important, we feel that who he was as a man was important.

"And it can be a little overwhelming sometimes," she admits. "But, I mean, I learned a long time ago that if you do the next right thing, incredible things happen."

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