Interview By Brian Mecinas
When Greg Freeman released his debut album I Looked Out back in late 2022, the budding artist didn’t anticipate the attention it would still be receiving over two years later. Following his recent signing to Canvasback/Transgressive Records, the Vermont-grown DIY gem has found new life within a winter re-release that features two additional tracks that draw listeners deeper into the album’s already gripping orbit. It’s a small taste of what’s to come in the new year and a mellow reminder that Freeman is here, working hard to bring new music out into the world.
The expanded version of the project comes right on the heels of a packed year of touring and live performances that saw Freeman spread his gospel across North America, laying the foundation for a career-defining 2025.
As I chatted with Freeman over the phone on a quiet Monday morning, he described the process of revisiting the album as both exciting and funny. “It was weird to be working on the new record while also figuring out the re-release,” he shares.
The re-release itself offers listeners two bonus tracks: an acoustic rendition of "Long Distance Driver" featuring Merce Lemon, and a sound collage titled "Sound Tests, Scraps, Lists." Freeman describes the latter as “a bunch of little ideas” woven into a single track, capturing the occasionally fragmented yet cohesive nature of his creative process. Meanwhile, the acoustic duet infuses a more intimate spirit into the song with layered vocals by Freeman and Lemon being gracefully underscored by a reoccurring harmonica track in between verses.
The stripped down, acoustic nature of the rendition is something Freeman notes could have been a bigger part of the original record. “There’s no acoustic songs on the original album, so this adds another element that could have been there in the first place,” he says.
In regard to what drew him to invite Lemon onto the song, it seemed that with their familiarity with one another’s music, it just made sense. “We were in Pittsburgh and she had a friend that had a studio there. We had done some tours together and she already knew the song. We came up with this nice slow, subtle harmonica for it. It was pretty organic,” Freeman recounts.
As we spoke, it became apparent to me that this sense of familiarity was more akin to camaraderie. Looking across all of Freeman’s endeavors, the common through line is the community he’s become immersed in throughout his time living in Burlington, Vermont. Freeman’s journey with I Looked Out, and his music as a whole, is deeply intertwined with the city’s music scene. Specifically with the people he’s come to know within it.
“There’s definitely a communal element to the albums that comes with living in a tight-knit place like Burlington,” he reflects. “A lot of the same musicians are on the first record and the new one, and they bring their own unique sounds and experiences from their own projects.”
As he prepares for what was implied to be a full sophomore LP in 2025, Freeman has taken inspiration from this community as he pushes his sound to new lengths. Working with producer and friend Benny Yurko, Freeman speaks with pride as he describes how the duo have been creating a record with higher production value and a freer, more experimental energy.
“A lot of the new album was recorded the same day we learned [to play] the song. Me, Zack, Benny, us three,” Freeman recounts. “It’s not like we rehearsed for a million years before we recorded. So a lot of it is free-flowing, it has that energy of- not everything is overly practiced or choreographed. I wanted there to be room for experimenting.”
This raw, dynamic approach to creating music seems to define Freeman’s work to some extent. If it was this approach that gave us the triumph that was his debut album, one can only imagine how breathtaking the new record will be.
For Freeman, the re-release of I Looked Out isn’t just an opportunity to look back; it’s a chance to connect with new audiences while staying rooted in the same independent spirit that made the record special in the first place. “I’m excited just to get it out. Keep writing new songs. I’m excited for people to hear the new stuff. The opportunity to keep playing music feels like a privilege,” he says. “To have people help you book shows and support your work—those are things I’m really grateful for.”
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