Craig Finn remains open to the possibilities alive in the world

The Hold Steady frontman, who performs solo at Stuart’s Opera House tonight (Monday, April 8), on eschewing cynicism and continuing to embrace empathy.
Craig Finn
Craig FinnCourtesy Big Hassle Media

In the past, it’s been easy to draw a line between Craig Finn’s solo work and the songs he penned for long-running Brooklyn band the Hold Steady. On his own, Finn said he has generally embraced intimacy, saving his more dramatic scenes for the band, which has the volume to match the outsized action. But that gap all but evaporated on Hold Steady’s The Price of Progress, from 2023.

“I think it really started to blur on that record,” said Finn, who will perform songs off his five solo records alongside a handful of unreleased new tracks at Stuart’s Opera House in Nelsonville tonight (Monday, April 8), joined by co-headliner Alicia Bognanno of the rock band Bully. “I’m thinking of the song ‘Grand Junction’ right off the bat, which is sort of a story where no one gets shot or robs a bank or falls off a roof.”

Rather, the narrator in “Grand Junction” journeys west only to learn that our problems have a way of tagging along with us. Events are similarly muted on tunes such as “Sixers,” which finds two young professionals try and fail in an attempt to find a connection with one another. Then there’s “Carlos Is Crying,” which lingers on a cubicle dweller as he breaks down over pitchers of beer at a generic sports bar, distraught by the numbing course his life has taken. “We started as skaters,” he reminds his friends. “Man, we used to glide/We used to hang like the smoke.”

While the settings might be smaller, the music remains epic, the Hold Steady bandmates crafting a surging cascade of guitars, harmonica and keyboards. “I think I was interested in that experiment, asking, what if you made these songs sound big?” Finn said. “What if you take ‘Carlos Is Crying,’ where this guy is bursting into tears at a sports bar, and then you try to make it sound epic?”

Part of this scaled-down storytelling could be attributed in part to the pandemic, which made the world in which many of us moved for a time significantly smaller. It’s also a natural side effect of Finn growing older, he said, the characters in his songs necessarily aging and slowing alongside the musician. When he wrote the songs for the Hold Steady album Boys and Girls in America, from 2006, Finn said the cast of characters populating the record were much younger than he was at the time – a gap that has since disappeared.

“As I’ve gotten older, the characters in the songs have tended to creep up in age,” said Finn, 52. “And now I think they’re fully middle aged and dealing with some of those things that middle age brings, and maybe a very specific kind of adult sadness. I got divorced young… well, in my 30s. But when people are breaking up and they have kids, there’s maybe a deeper, heavier feeling to dig into. … And when things fall apart, it can cause us to reflect a little bit more on what we want out of the life that we have left.”

Exploring this idea on record has led Finn to ask similar questions of his own existence, and he’s come to a realization that, unlike Carlos and his tear-streaked Skippers menu, he’s actually managed to carve out a pretty good life for himself. Recently, Finn attended his 30th Boston College reunion – “Which I realize is not very rock ‘n’ roll,” he said, and laughed – and walked away struck by a deep sense of gratitude. “It really put a glow on me and made me feel fortunate to know a lot of good people, and to see how cool and positive and wonderful a lot of them turned out,” he said. “I mean, everyone struggles, obviously. And no one is going to come to a reunion and tell you their deepest, darkest secrets. But it was really profound, and I was surprised how much it adjusted my outlook.”

For much of his life, Finn has embraced his generally upbeat nature as his “superpower,” as he termed it. It’s a trait consistently present in his songwriting, where even at their most shattered and desperate, the characters in his songs never give in. Finn's deep, expanding catalog, in turn, is populated with people who refuse to settle, and who are almost universally ill content to be defined by their circumstances. The musician traced this deepening sense of empathy in his writing in part to his mother’s death 10 years ago, sharing that in the process of navigating grief, he also became awakened to the reality that we’re all bonded in some way by loss.

“And you get on a crowded subway car, where things that might have previously annoyed you, like, ‘Oh, this guy is standing on my foot, this sucks,’ and you almost brush it off,” he said. “It’s almost like you can say, ‘All these people suffer. All of these people have mothers that will one day die. They’ve lost friends, like we all have.’ And going through these sorts of life changes, it’s something that puts you in touch with empathy. And in some way, it makes you a kinder person.”

On recent records, Finn has combined this more profound sense of empathy with a long-developed curiosity that he said led him from an early age to linger on the inner worlds of the people he would encounter going through his day. “I’ve always been an observer. Even though I talk a lot, I know when to be quiet, and I used to really try to make myself small to see how people acted if they sort of didn’t know I was there,” he said. “And in that, I think you’re trying to find a window into what people are doing on their own, when they’re not performing for you. That idea that everyone has a story is interesting to me. If you’re in Pensacola, Florida, and you see a house, it’s like, ‘I wonder what goes on in that house.’ Or you go on vacation, and you’re on a train, and you start to make up stories about the people who you see on the train with you.”

One could easily imagine Finn encountering the narrator of “Sideways Skull” on the subway in Brooklyn – the song delving into the existence of a musician who keeps her rock ‘n’ roll dreams alive while living in a halfway home, and who Finn brings to life with novelistic detail. She performs in front of a backdrop made from a bed sheet and painted with a lopsided pentagram, and she wears a jacket “held together by rock band patches.” And like the characters who exist in the musician’s best songs, she’s bruised but still kicking, Finn delivering through her a line that could stand as his own credo: “The trick is not getting cynical.”

“And while I think that comes easier to me than a lot of people, there are times I have to work at it, where I have to say, ‘Okay, let’s slow down and pay attention to the good things here,’” Finn said. “Because I do think once you let yourself become too cynical, or too angry, it’s over. … I think trying to stay in touch with the possibilities of the world is how you stay alive.”

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