At 40, Arlo McKinley Finds a Champion in John Prine’s Oh Boy Records

Last year, singer-songwriter Arlo McKinley played a set at the intimate Nashville venue the High Watt. A couple of very important things happened that evening. For one, the Cincinnati-based performer landed his current booking agent out of it. Secondly, among those in attendance was Jody Whelan, Director of Operations for Oh Boy Records, whom McKinley had gotten to know after playing an AmericanaFest event for the label a year earlier. At Whelan’s side was Oh Boy’s star artist, John Prine.

“It’s the only time I’ve ever been starstruck. I tried not to fanboy out over it and play it as cool as possible,” McKinley recalls of meeting one of his songwriting idols. “We talked for a brief moment. He was excited to see me play.”

Turns out, Prine and the Oh Boy team were excited enough that they also wanted to work with McKinley — he became the last artist that Whelan and Prine signed to the label before Prine’s death in April. On August 14th, Oh Boy will release McKinley’s album Die Midwestern, an LP that finds the 40-year-old looking back at where he’s been from the vantage point of hard-won experience.

Born and raised in Cincinnati, McKinley (a stage moniker he adopted years ago) grew up in the city’s punk and hardcore scene, playing bass in bands. Later he joined the folk duo the Great Depression with Jeremy Pinnell, where he largely served as a harmony singer. Then in 2014, he reemerged as a solo performer with the album Arlo McKinley & the Lonesome Sound. He embraced the D.I.Y. spirit of his punk days to help spread the word.

“That [scene] was a big part of what made me realize that you can do it,” he says. “And so when I first started writing these songs, that’s the approach that I took. I put out that album myself, that first one, and kind of just was calling around writing emails to get shows wherever we could.”

One of McKinley’s older songs titled “Bag of Pills” garnered him a lot of attention, including that of Oh Boy (Prine thought it was a “good song,” one of his highest forms of praise). McKinley performed it in a 2017 video for SommerSessions, which went on to rack up 3 million views and earn him comparisons to Colter Wall and Tyler Childers (with whom he shares a manager).

“His voice is the first thing you notice,” Oh Boy’s Whelan says of McKinley, whose singing has traces of Childers’ Appalachian drawl along with Jim James and Jay Farrar. “But you actually start listening to the words and it’s like, oh, there’s a message, he’s not just a singer. He’s got something to say.”

“Bag of Pills” stems from a rough period in McKinley’s life when he was cash-strapped and seeing many of his friends struggle with opioid abuse. At the time, the Cincinnati area and neighboring Kentucky were being ravaged by addictions.

“I got caught up just like a lot of people,” he says. “And it just gets to the point where you’re no longer having fun with it. And now you need it just to have a conversation with somebody. That was just a sad thought to me.” The casualties of the opioid crisis also course through McKinley’s standalone 2020 single “Ghost of My Best Friend,” written for a close acquaintance who overdosed. The tragedy multiplied — McKinley’s mother died in early 2020, not long before Prine.

“Those are the three people that I really wanted to hear the record,” McKinley says. “And it’s just such a fucked-up time, because now they’re not going to hear it.”

These days, McKinley is free of opioids, but he writes about those experiences knowingly. “We’ll get high and talk until morning/Then you can catch me sleeping,” he sings in “Bag of Pills.”

“Luckily I came out of that, because I’ve seen a lot of people that haven’t,” he adds.

“His music’s really honest about a lot of that stuff, but I don’t think he ever glamorizes it,” Whelan says. “He drops you into the eye of the storm.”

Die Midwestern, which McKinley cut at Sam Phillips Recording Service in Memphis with producer Matt Ross-Spang, fleshes out this chapter of hard times, dealing in heartbreak and restlessness along with the scourge of addiction. But it isn’t an album about succumbing — it’s about the decisions you make when you’re in the middle of it, and the steps you take to start the long process of moving on.

“He’s had a pretty tough life, but in his songs you don’t hear bitterness or anger,” Whelan says. “Some of it’s certainly directed inward, but it’s not angry.”

The fiddle-laced title track offers a sense of place, coming not from the rural South as many country songs do, but from an industrial city at the edge of Appalachia. “Another Cincinnati Saturday night/And I hate what that’s become,” he sings, wondering if he’ll ever leave the place he calls home and what things he’ll miss if he does.

“[It is] about that struggle of deciding, ‘Do I move on out of here, away from things that I love and also hate, or stick it out because it’s the only thing I’ve ever really known?’” he says.

Ironically, for all the darkness that hangs in the album’s margins, the song titled “Suicidal Saturday Night” might be its most musically upbeat. Rather than self-harm, it’s about taking musical opportunities seriously — something McKinley didn’t do so much in his earliest days when touring felt like a nonstop party. These days, he tries to treat it like a job and get enough sleep for the next gig.

“I often say I have enough of those party stories to write five books,” he says. “I don’t need any more of those. Now it’s just good to be able to be completely focused on the opportunity that’s been given to me.”

The album wraps up with “Walking Shoes.” It’s the most hopeful song of the lot, a relaxed country-rocker that sees McKinley bidding farewell to past mistakes and trying to move forward.

“In some ways I see that as where Arlo is in his life, trying to walk away from stuff that he knows is bad and destructive but not putting blame on anybody,” Whelan says. “And with an eye toward a brighter day.”

While it points toward a better future, McKinley says he may not be completely finished writing about the tumultuous period of his life.

“I’ve got a whole ‘nother set of songs that I would like to get out that touch on the same stuff,” he says. “But a lot of the newer stuff I’m writing, it’s a new chapter. It’s just about other things.”

That’s where age is an asset for McKinley. Going through his experiences, emerging on the other side with some perspective, and having renewed seriousness about his musical career as he hits middle age — those are all strengths he’s matured into.

“I wouldn’t have been able to do this at a younger age. Where I was in my mind and things going on in life, I just wouldn’t have been able to focus on it as much as I should have. And I like that I’ve lived 40 years — now I kind of just look back on everything and write about it all. Because I thought I knew everything in my 20s, but I didn’t know anything.”

Such wisdom and self-awareness is earned over time. His path may have been a circuitous one, but McKinley’s right where he needs to be.