About Ryan Sweezey
The story behind the songwriter
Music Was Always There
I've loved music for as long as I can remember.
I grew up on the North Shore of Massachusetts, just outside Boston, in a family where music was a big part of how we spent time together. My dad introduced me to Jimmy Buffett when I was little, and I’d wander around singing obscure Buffett songs by the age of five. He and I spent years hunting for music together and going to see The Rolling Stones, The Who, Tom Petty, and others.
As I got older, my taste expanded into the alternative rock of the '90s and early 2000s—Matchbox Twenty, The Goo Goo Dolls, Counting Crows, Augustana and others.
I've always been a curious person, and I think that's a big part of how I relate to music. I hear something I love, I want to understand how it came to be, and then I get inspired to make something of my own. Little did I know those early passions would go on to shape the rest of my life as a professional musician.
Finding My Voice
My first guitar didn't exactly work out. My parents gave me an acoustic when I was young, but it sat largely untouched in a closet until the bridge snapped off on a humid day.
A couple years later, they tried again. This time it stuck.
I was twelve when I started taking guitar lessons, and I became obsessed. I learned quickly, preferring to learn actual songs rather than scales or technical exercises. I'd bring my teacher CDs and ask him to show me how to play them.
For a while, I thought guitar was going to be my thing.
Then I discovered I could sing.
As a freshman in high school, I signed up for a student coffee house and played Bruce Springsteen's "Growin' Up," having never sung publicly. I was nervous, but I surprised people—including myself. That led to choruses and musicals on top of bands.
Around the same time, I started writing songs of my own. At first, songwriting was simply another way to express whatever I was thinking or feeling. I wasn't thinking much about an audience or what kind of artist I wanted to be. I just knew that putting something into a song could make it easier to understand.
For college I went to Northeastern University, where I minored in music, joined an a cappella group, and started playing my first solo gigs.
Becoming a Working Musician
My first paid gig was at a bar called Harrington's when I was nineteen. I had no professional performing experience, but my mom knew the owners and they were willing to give me a shot. It went well, and one gig led to another until I had built up enough work through college that I decided to pursue music full-time after graduation.
At the same time, I became part of Boston's singer-songwriter community, playing open mics around Cambridge and Somerville and meeting writers who pushed me to get better. I had always written as a form of personal expression, but being surrounded by other songwriters made me think more about craft—and about how something drawn from my own life could connect with someone else's.
For a few years, I threw myself into performing, writing and recording. I learned a lot, made some important music, and gradually built a life around being a musician.
Eventually, though, I found I needed to step away.
Finding My Way Back
Seeking a change, I moved to Vermont in 2016, where my sister lived. For a while, I took a real break from music. I still played the occasional open mic, but I stopped trying to make music my entire livelihood. I took a full-time job, always assuming I'd eventually return to music full-time.
I never quite did.
Instead, I slowly started rebuilding my music career in Vermont. One show became another, and eventually I was playing nearly 100 shows a year while working full-time. I've scaled that back some, but I still play dozens of shows throughout Vermont and New England.
Somewhere along the way, I realized I didn't need music to be my entire livelihood for it to remain a huge part of my life. The life I built wasn't the one I'd imagined when I first decided to become a full-time musician, but it turned out to fit me better. Music is still how I process the world, express myself, and connect with people in a way that sometimes feels more natural to me than conversation does.
Making the Songs Real
Performing is a huge part of what I do, but recording may be my favorite part of the creative process. I love watching something that existed only in my head become real through a strange combination of performances, instruments, sounds, reactions, mistakes, happy accidents and ideas I never could have imagined on my own.
My relationship with the studio has changed a lot over the years. On my first albums, No Hollywood Star and Fall, I was still learning what making a record even meant. With Starting Over, I became more intentional about the sound I wanted and learned how much collaboration could reshape a song.
Eventually, I stopped worrying so much about what my records were supposed to sound like. Working with producer Christopher Hawthorn on Out Searching taught me to approach each song on its own terms and ask what it needed. That freedom became an important part of how I make music.
By Maybe Magic, I had grown into a co-producer, bringing years of recording experience—and a much stronger sense of when to trust my own instincts and when someone else's idea might take a song somewhere I never expected.
I've gone from being an awkward teenager who was uncomfortable in the studio to someone who genuinely loves recording. I still never know exactly what a song will become when we start.
That's probably my favorite part.
The Midnight Walkers
In 2022, I put together some musicians who’d been part of another project with me for a full-band show to celebrate the release of the Out Searching album. The show went well and before long, what started as a one-off had become the full-band version of Ryan Sweezey.
I wanted “Ryan Sweezey” to remain the artist and recording name, while making it clear when a show featured the full band. So when the band joins me onstage, we're Ryan Sweezey and the Midnight Walkers, a nod to an old roommate's song. With the Midnight Walkers, the songs get bigger, louder and more energetic, opening up possibilities that aren't there when I'm playing alone.
Why I Write
I write because it's one of the ways I make sense of everything going on in my head. I have a lot of thoughts, and writing gives me a way to focus them, shape them, and get them outside of myself. Sometimes I don't even realize what I'm trying to say until I start putting it into a song.
But I don't write only for myself.
I write songs for people who spend too much time in their own heads. The ones replaying conversations, questioning decisions, searching for hope after difficult seasons.
In other words, people like me.
If you've ever needed music that sits with you like a companion instead of pretending everything's okay, you're in the right place. I'm not here to pretend I have all the answers. I'm here to make something honest out of the questions—and hopefully give you some company while you're figuring out yours.
Still Figuring It Out
I'm still figuring things out. I suspect I always will be. And honestly, I'm okay with that.
I'm still a pretty quiet person. I'm more comfortable observing than leading the charge, and I'm usually more at ease having a meaningful conversation with one or two people than trying to work a room full of strangers. But I've found that a stage gives me a strange kind of freedom. I can say things through a song that I'd probably struggle to say in conversation, and for a few minutes, a room full of people can feel surprisingly intimate.
I think that little kid singing Jimmy Buffett songs in the kitchen is still in there somewhere. I still get excited about a great song. I still get inspired to pick up a guitar after hearing a great record or coming home from a great show.
The difference is that now I get to be part of creating that feeling for someone else.