Brett Dennen is a fan of great songwriters, and it shows in his work. His ability to tell a story—sometimes whimsical, sometimes heartbreaking—and deliver it wrapped in infectious hooks defines Dennen’s facility as a student of folk and rock music.
His unique style launched a fandom of more than 75 million streams on Spotify for “Ain’t No Reason.” Dennen toured with John Mayer, played the festival circuit, and had a number of songs placed in television shows including “Comeback Kid (That’s My Dog),” the theme song for the NBC comedy “About A Boy.”
The California native grew up exploring the outdoors, writing music, and painting. On his current Art is Life tour, he mixes it all together: a live performance that incorporates storytelling, visual art, and audience participation. Brennen spoke to C-VILLE about his vision for the upcoming shows at The Guild on September 26.
C-VILLE: I understand you are bringing a unique show to town. Tell us what it’s all about.
Brett Dennen: It’s a concert, but it’s an interactive concert. It’s completely different every night.
I do it in two sets. The best way I can describe it is I’ll have these paintings behind me and I’ll bring one of the paintings up next to me and I’ll sing a song that I choose in the moment to go with the painting.
It’s pretty fun because people start seeing things in the paintings that I didn’t know were there—you know everybody has a different take.
In the second set the goal is to get people to suggest songs to go with the paintings that are on stage. … I take all cards that [the audience] fills out and I put them in a box and I just start pulling them out at random. And it’s really fun because people say all sorts of things, like you just wouldn’t believe.
Tell us about something fun that has happened in one of these sets?
We did a wedding once during a song. These people were talking about how they wanted to get married, but they couldn’t because same-sex marriage wasn’t passed in their state, but then when it finally happened, they got married to this certain song, and so they wanted to hear that song.
I was like, “Let’s reenact your wedding right now.” So the crowd turned into the wedding audience and they walked down the aisle and they got up on stage and danced to the song. I try to be open to whatever happens and thankfully the audience has always been open to it.
How long have you been performing like this?
I got the idea for it last year and I did three weeks of shows in the Midwest trying it out and I learned a lot and I loved it.
I thought, okay, in 2026 I want to try and get better at this and to take it to as many markets as I can. And it’s been a good vehicle for me to produce a lot of art because every time I do a new tour I make a bunch of new paintings for it to keep me fresh.
What do you do with the paintings when you’re done with the tour?
Well, I tell people if they want them, they can buy them, and if not, I’ll just take them home and I don’t know what I’ll do with them.
You’ve connected your creative life to the outdoors through an annual Camp Dennen. How does that compare to performing?
Well, it’s the same thing, really. It’s a bunch of people getting together. And we go to a really fun summer camp and instead of it being like a festival where I’m performing the whole time, I’m a participant. I’m there with them.
We put a theme together and come up with a bunch of activities. … But it’s really about just people, coming together, getting out of town, getting off their phones, and building a community in nature.
How is it that you chose a musical path for your creative expression?
Oh, I don’t really know,. It’s just at the time that I was finishing up with college and I was playing a lot of music and I was in a band. I was really falling in love with the idea of writing songs and it just seemed to be that’s what I was doing.
Now that I’m older and have done music for a while, I’m starting to get back into painting— it’s really attractive to me in a way that never was before.
Do you have a place that you go, or a process for songwriting?
It just comes. I always thought that it would be cool to have a little recording studio, but I’ve never lived in a place that has enough room for that. Where I live now, I have a little creative shed in the backyard that I paint and write in, but I’ve learned over the years that you can write a song anywhere. … The songs are just kind of always being thought about and being worked on in my head, and then there’s some times where I’ll be sitting down for hours, actually, just finishing them. But a lot of the time they’re just kind of all up in the air swirling around.
What can we expect when you come to Charlottesville?
Well, I think it’s two shows on the same day, because it’s a small venue—I don’t even know if the paintings are all going to fit on the stage. … I have six big paintings. So, dare I say that these two shows might be my two favorites, just because I know that when it’s less of a typical venue … something about that sort of breaks down the barrier between the stage and the audience and usually makes for a special atmosphere.
Brett Dennen combines a love of painting with a love of songwriting, and asks the audience to weigh in, on his Art is Life tour.