Bennett Woolsey: Stories From the Road and the Heart

Bennett Woolsey: Stories From the Road and the Heart

There’s a particular kind of artist who thrives in motion — someone whose creativity sharpens on long drives, backstage laughter, and the quiet moments between cities. Bennett Woolsey is one of those artists. Splitting his time between Nashville and Los Angeles, he’s built a life that blurs the line between songwriter, guitarist, collaborator, and storyteller.

When we caught up with him at the Moroccan Lounge — where he was performing as the touring guitarist for maryjo — Bennett arrived with the same energy that defines his music: warm, thoughtful, and quietly electric. His journey has already taken him from TikTok writing challenges during the pandemic to millions of streams, cross‑country tours, and a growing catalog of deeply personal songs.

This conversation traces that path — from the early spark of Jimmy the Chameleon to the emotional weight of his new EP, the joy of touring with maryjo, and the nostalgia‑soaked storytelling that anchors everything he writes.

We’re here with Bennett Woolsey at the Moroccan Lounge. First of all, Bennett, where are you based out of, and what’s your local music scene like there?
I’m currently based out of Nashville, Tennessee. I work in a music studio as my nine‑to‑five, so I’m pretty involved in music even when I’m not writing. It’s a really collaborative scene, and I’ve been back and forth between LA and Nashville for about four years now. I’ve built a lot of really good friendships in the scene. It’s been fun.

You played out here at We Found New Music. What was that experience like?
That was me getting my reps in, which was amazing because Grant is really generous. I was extremely nervous to start playing — I’d been writing all the time and showing my friends, but I’d never really shown the world my music. Those shows were the first steps toward putting myself out there, and I was lucky to do it in such a professional setting.

How has this tour with maryjo been going so far, and what have been some of the highlights?
It’s been so much fun, dude. Every day is something new with her. I always tell her she has a superpower — it’s hard to stay optimistic, loose, and silly on a long tour, but she always seems to be in that mood. She’s a good friend when you need her to be, but for the most part it’s just fun and games in the best way possible.

Canada was a big highlight. We had a drive from Vancouver to Calgary — I’d never been to Calgary before. Ten hours through beautiful mountain ranges… I don’t even know, dude. That might have been my favorite part of the tour.

Before we get to your songs, let’s talk about “Used to You” with maryjo. How did that come about, and are you playing it on the tour?
We are playing it — we’ll be playing it tonight. I wrote that song a few years ago, I think in 2022. I originally wrote it for myself, and since me and maryjo have been best friends for so many years, I was excited to show her. She had worked with the same producer before, and when I played it for her, she said she wanted to turn it into a duet.

We reworked a few lines, she came into the studio, and it’s been our song ever since.

Let’s talk about your new song “Chevy Chase.” What was the inspiration behind that?
That one’s based around nostalgia. Chevy Chase is just an actor who reminds me of holiday times — sitting around the TV with my family when I was younger, watching Christmas Vacation. Everyone’s always like, “Dude, what is going on with the ‘Chevy Chase’ song?” because it’s a unique title. But yeah, that’s basically the idea.

And your recent single “Cigarettes and Alcohol” — what inspired that one?
It’s a juvenile name, I know. I wrote that song on New Year’s Day maybe two years ago, after a night out with my friends and an early morning flight the next day. I was battling whether to sleep for two hours or just stay up, and I ended up writing instead.

It’s another nostalgic one — missing home, missing my friends, realizing how fast time flies. That’s what naturally came out that night.

In 2020 you released “Jimmy the Chameleon” with your band Brookside. What was the inspiration behind that song?
That one came about in a funny way. I had started doing a writing challenge on TikTok. I was a senior in high school during COVID, and “Jimmy” was day four. The previous days were pretty bleak — people were suggesting dark topics like “write about my relationship with my father,” and I tried to honor those.

Then someone commented asking for a song about a chameleon who gets lost in the woods. I thought it would be more lighthearted, so I gave that one a shot. And that’s how it became a thing.

What was it like releasing music during the pandemic?
I think a lot of music careers started then. People had so much time, everyone was stuck inside, and releasing music became a way of connecting even though you were still in the same four walls. A lot of people moved past the fear of “I don’t know if I’m good enough” and just put themselves out there. That was definitely me. I didn’t tell any of my friends I was starting a TikTok — I just let it do its own thing.

I looked on Spotify — “Jimmy the Chameleon” is now at twelve million streams. What does that number mean to you?
Dude, it’s the biggest blessing and curse ever. Until something surpasses “Jimmy,” I’m known as the “Jimmy the Chameleon guy” — which is awesome. I’m extremely thankful for what that song has done for me and the rooms it’s allowed me to enter.

But twelve million is bizarre. It’s hard to conceptualize that number. And it’s funny because it was one of those songs that came out in fifteen minutes, while songs I spend way more time on don’t get the same recognition. I think that’s the case for most musicians.

Is there an EP on the way?
There is. We’re releasing a song every four to five weeks. The next one is “Spirit Wine,” coming out on the 28th or 30th — I think we aligned it with the 30th because that’s the last show on this maryjo run.

“Spirit Wine” is my favorite song on the EP. It’s track three of five. So the full EP should be out in about eleven weeks.

Tell me about “Spirit Wine.”
I usually write in first person, but this one is more of a story between two people in a toxic relationship — addiction to substances, addiction to each other, and the fear of letting go. It’s easy to fall back into the comfort of routine instead of doing the hard thing and removing yourself from a situation. That’s the idea behind it.

If you could open for any band or artist, now or from the past, who would it be?
So hard. It would be awesome to open for Billy Joel — the ultimate songwriter. Current day, I’d probably say The Backseat Lovers or Mt. Joy. I’ve pulled a lot of inspiration from both. Mt. Joy at Red Rocks would be the dream.

If the music of Bennett Woolsey was a donut, what kind would it be?
My god, dude. That’s a hell of a question. I’ll go with strawberry. Not the classic glaze or chocolate, but still loved by many.

What would you like a listener to remember after hearing your music for the first time?
The songwriting and storytelling. It’s rare now for people to sit down and really listen to the words. I think music reminds everyone that we’re sort of on the same team. That’s what I’d hope they take away.

Any messages for people who’ve been following your career — or discovering you for the first time?
I’m so appreciative of every single person who reaches out. It’s surreal, especially on this tour. People have brought me notes, mementos, and really sweet messages. It’s a strange feeling to be loved by complete strangers, and I’m extremely thankful. I welcome any new listeners.

In Conclusion

Bennett Woolsey is an artist who writes with the honesty of someone who’s lived a lot in a short time — and who’s still paying close attention. Whether he’s onstage with maryjo, releasing nostalgic singles, or crafting stories that feel both intimate and universal, Bennett’s work carries a sincerity that’s impossible to fake.

As his EP rolls out over the coming weeks, and as his audience continues to grow, one thing is clear: Bennett is building a career rooted in connection — the kind that starts quietly, spreads steadily, and stays with you long after the last note fades.

(Interview by Ken Morton – Photos by Karyn Burleigh of Rock Edge Photography)

Bennett Woolsey on Instagram