“When was the last time you listened to music with someone?” asked Howie Day in an email interview with The Daily.

I can’t remember. In anticipation of his upcoming show at The Ark, the acoustic-rocker corresponded with The Daily, and I’ve been asking myself his question ever since. It’s frustrating in its passive dig at the truth: There’s some music that exists to move, and it’s not often that people actually take the time to be moved by it. Day lives somewhere in this oasis, playing with a grit and vulnerability that doesn’t demand to be heard, but gently begs that you — at the very least — try.

“A show gives you a solid hour or so to get people to sit down and feel something,” Day wrote.

A wunderkind, Day has been playing piano since he was five, and he started gigs at just 15. For someone still so young, he has an almost 20-year career backing him, making his concerts a rare melding of youth’s effervescence and wisdom’s skill.

“The live loop sampling songs (like ‘Bunnies’) are still interesting to me because they change night to night depending on the actual space and the energy/mood of the audience,” he wrote. “I also enjoy playing something somewhat loud and cathartic followed by something very quiet and vulnerable. This makes for a dynamic experience for me, and hopefully the audience, too, and is another thing missing from popular music today.”

You probably know him from “Collide.” A colossal hit from his 2003 album, Stop All the World Now, it embodies all the inexplicable, stunning, heartbreaking longing that was early 2000s singer-songwriting. The intro still gives me goosebumps. But, it’s not Day anymore, and that’s OK (dare I say, for the best).

“After that, I found myself in a changing and declining industry that was solely interested in reprising that moment,” Day explained. “Since then, it has been a decade of fighting and falling out of favor with an industry that doesn’t understand itself.”

He’s an underdog, and it’s this innate scrappiness that makes Day so endearing.

“As much as I have been discouraged by the way the music ‘industry’ has evolved over the last twenty years, it has nonetheless come with some pretty amazing opportunities and experiences,” he wrote. “One of my favorite experiences I find myself in over and over again is being isolated in some far-off place at the end of a tour, and existing in this space where I’m purely an observer, as my own life is wildly decelerating from weeks or months of performing and traveling non-stop. I see and hear things so much more vividly in these moments, and it’s amazing. Any art form should strive to gently (or not-so-gently) guide people to this place.”

Having worked long enough to be disillusioned by human nature, Day rejects the notion that there’s anything to disillusioned by.

“Human beings inspire me. Their resilience, curiosity, empathy, and willingness,” he wrote. “We live in this crazy world, and most of us still find the motivation to make it happen, whatever ‘it’ is. We’ve been at it for tens of thousands of years, but the moment we find ourselves in, now, where everything is just changing and progressing at breakneck speeds, is also very interesting. I feel pretty lucky to be alive to see it.”

Looking forward, despite pressures to recreate his stardom circa 2003, Day is fervent and ready for wherever his life may turn.

“I’m always dreaming of new possibilities, new paths,” he explained. “I don’t know where I’m going; it’s a road trip with no defined destination, no directions. I feel beyond lucky that I get to live the kind of life that meanders! I don’t even know how much longer I’ll treat music as my primary thing. There’s lots to discover out there, and that’s exciting.”

Howie Day will play at The Ark this Sunday at 7:30 p.m. Go with a heart wide open and listen to his music with someone else.

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