Pierce Crask on Songwriting, Storytelling, and Why Listening Rooms Matter

Live at Wesley’s Place — Friday, January 9

We’re excited to kick off our 2026 season with Pierce Crask, a Chicago-based Americana singer-songwriter whose music is packed with craft, heart, and the kind of lived-in honesty that’s made for a listening room. Ahead of his Friday, January 9 show at Wesley’s Place, I asked Pierce a few questions about songwriting, performance, and what makes an unforgettable night of live music.

His answers are thoughtful, funny, and most importantly, makes me even more sure this is a show you don’t want to miss.

Here’s my Q&A with Pierce:

Q: For someone who’s never heard you before, how would you describe a Pierce Crask show in three words?

Pierce: “Dynamic, heartfelt, entertaining.”

I love that summary. If you’ve been craving a night out that feels both meaningful and fun, those three words should stop you in your tracks.

Q: You’ve been performing a long time. What’s something you’ve learned about connecting with an audience?

Pierce: “I’ve learned that if you put expressing yourself to an audience above impressing an audience, you have a much greater chance of connecting with them.”

That line says so much about why Pierce works in a space like Wesley’s Place. It’s not about flash, it’s about truth. That kind of sincerity has a way of pleasing a room full of listeners.

Q: What do you think separates a great songwriter from a good songwriter?

Pierce: “If I may paraphrase Bob Dylan, I think the great songs are the ones that sound almost magically written… a perceived effortlessness… as if the writer just put their antenna up, let the song come in and then it just poured out of them. The great writers can get to that place.”

There’s something inspiring about that: the idea that songs can arrive like weather, if you’re paying attention.

Q: Where do your songs usually start?

Pierce: “My songs usually start with actual life events. The title song on ‘Rising River’ was inspired by a flood in my basement. ‘Well Crap, My Basement Flooded’ didn’t make for a very interesting song, but it set me on my way to ‘Rising River’!”

I love this answer because it shows Pierce’s mix of humor and heart. He can start from something ordinary and turn it into something worth singing.

Q: Which song is getting the biggest reaction right now?

Pierce: “‘Butterfly Song.’ It’s a very simple, direct and succinct song with a clear message people seem to really relate to.”

That’s a great hint for first-time listeners: sometimes the most powerful songs are the simplest ones—especially when they land in a room that’s really listening.

Q: What do you hope people feel when they leave your show?

Pierce: “I hope people leave the show feeling they got their money’s worth… that I gave them the best show I possibly could… and they’ve been able to escape the insane world on the other side of the venue door for a little while.”

That’s exactly what we love about live music at Wesley’s Place: it’s a reset button. A breather. A night that feels human.

Q: Your sound includes slide guitar and harmonica—how did that become part of your style?Pierce: “I’ve always been enamored with slide guitar… Duane Allman, Warren Haynes, David Lindley, Leo Kottke… I found I had a knack for it; and it set me apart from other performers at the time. As for the harmonica—girls seemed to like it.”

A perfect mix of musician insight and a laugh. (Also: yes, we want to hear that slide guitar in the chapel.)

Q: What makes a listening room different from a bar or a festival stage?Pierce: “Because it’s a listening crowd in a quiet room, you can throw in subtle nuances… that would be lost otherwise. That makes for an unbeatable experience for both listener and artist!”

Couldn’t say it better. That’s the whole point.

Q: Any special reason this show will be unique?

Pierce: “It will give me the rare opportunity to bring out my vintage guitars… Martins and Gibsons from the 20’s and 30’s… plus my steel guitar… and don’t fret, Netflix will still be there when you get back home!”

Vintage Martins and Gibsons in a great-sounding room? That’s the kind of night people talk about afterward.

Pierce Crask at Wesley’s Place

📅 Friday, January 9

🕖 Doors 6:30 • Music 7:00🎟

$20 but $2 off online with code EARLYBIRD at checkout

📍 La Grange, IL