A Chat with Peter DiMaggio (19.11.25)
Peter DiMaggio is a multifaceted artist whose talents span acting, music, singing, songwriting, and composition. His new single, ‘Fly Away’, marks the first official release under Passeri Records. We chat with Peter DiMaggio to discuss his music, creative journey, and what’s ahead.
OSR: You wear many hats from actor, composer, producer, to performer. How do those different creative sides inform each other?
DiMaggio: I was often told by many professors and instructors that I needed to choose one area on which to focus if I wanted to have a successful career in the arts. Though I think those mentors had good intentions, I have found the opposite to be true. All these different modes of creative expression inform each other. Acting makes me a better songwriter. Songwriting makes me a better performer. Producing allows me creative control and ownership of what I create. One well-meaning professor told me, “A jack of all trades is a master of none.” But I found the second half – and more important half that she left out – of that quote to be much more meaningful: “…but oftentimes better than a master of one.”
OSR: ‘Fly Away’ feels deeply personal. What moment or realization sparked the idea for this song?
DiMaggio: It was less of a moment of realisation; it felt more like sifting. Like how old prospectors panned for gold in the California rivers? I had the last two lines of the chorus come to me first, seemingly out of nowhere, as I was playing around with the main riff that you hear in the song. From there, it was just about sifting through memory to find out where that inspiration came from and why.
OSR: What was the most challenging moment in bringing ‘Fly Away’ to life, creatively or emotionally?
DiMaggio: I sat on the chorus and verses of this song for what felt like the longest time because I couldn’t figure out what to do with the bridge. Creatively, the solution ended up being simple: if “today, I’ll pack up my things”, then the bridge should be about what happens tomorrow if I do. It was much more difficult emotionally. What ended up falling out of me for the bridge, which I wrote in one sitting, was a lot of truths that I had previously neglected to admit to myself about that relationship. How did I let it go on that long and get that bad? Coming to terms with that was the most challenging piece. But once I did, the writing itself was easy.
OSR: You’ve described the song as being about breaking free from a toxic cycle. Was it difficult to revisit those emotions creatively?
DiMaggio: It was actually extremely liberating. The outro was probably the easiest part to write. It came from the same writing session as the bridge. I figured if the song was about the feeling of being trapped, then the narrator shouldn’t successfully escape. That would be too easy. And it wouldn’t be true to the version of myself that I was writing about. It was liberating and affirming to compare the perspective of the narrator of ‘Fly Away’ to the one writing it in the wake of that relationship. Two very different people. The latter is much healthier and more sure of himself.
OSR: The production feels cinematic. How did your background as a filmmaker influence the sonic choices on ‘Fly Away’?
DiMaggio: I actually think it was less my film-making background and more my acting background that informed the production. I don’t think every song I release will sound “cinematic”, though the story and imagery in this particular song demanded it. Acting, to me, is about lifting the story off the page in a way that is captivating, true, and SERVES the playwright’s intent. Cinematic production SERVES the source material of this song. My co-producers, Tyler DeTulleo and Charlie Burket, understood that vision and helped me execute exactly what I felt represented the heart and core of ‘Fly Away’. As a team, we were able to “make it more of what it is” – this is a quote from my directing professor from Boston University, Clay Hopper. He always says the goal of directing is to make the play “more of what it is” rather than pasting ideas on top. I’ve taken that advice and applied it to every creative endeavor I’ve attempted since, to overwhelmingly positive results.
OSR: ‘Fly Away’ marks the first official release from Passeri Records. What inspired you to start your own label?
DiMaggio: I saw an opportunity to create music and more on my own terms, but I couldn’t find a solution in the industry as it stood to fill that space. So I set out to create my own space. It’s also a bet I took (and am currently taking) on myself and my vision. I really believe that I can create a community of artists that would allow me to fulfil this simple yet difficult goal of self-production and ownership. And the long-term goal, and true inspiration, is that if this bet pays off for me, it means that I can provide other emerging, talented, and dedicated artists with the same support. I think that’s a really beautiful and worthwhile mission.
OSR: You’ve said Passeri Records is about ‘creative community and empowerment’. How does that vision play out in practice?
DiMaggio: It takes a village. In the short term, it’s been about highlighting all of the incredible artists – directors, cinematographers, production designers, producers (both music and film), actors, studio musicians, and more – that it took to make this project a reality. I’ve built a deep network of trusted collaborators, but community is about more than that: it’s about uplifting those people in a way that benefits everyone. The empowerment has come from proving we can make industry-quality product outside of the constraints of a major label. The retention of creative control is also wildly empowering. This will be central to the way in which we expand Passeri Records when the time comes.
OSR: You’ve talked about redefining what independent artistry looks like. What’s the biggest misconception about being an indie artist today?
DiMaggio: That you have to do it all on your own. I attempted exactly that a few years ago, and the best thing I ever did was admit to myself that even though I could produce, mix, and master all of my music on my own, the music itself would benefit much more from finding people to work with who are better at all of those things than I am. There’s strength in asking for help.
OSR: And what advice would you give to other artists looking to take ownership of their music?
DiMaggio: Find your team. Find the people you trust and who understand, and are excited by, your vision. (It’s also a plus if they are good at their job). And my secondary answer is to sign with Passeri Records once we’re in a position to sign and fund more artists while leaving them with ownership and creative control.
OSR: What’s next for you and Passeri Records, and how does ‘Fly Away’ set the tone for that journey?
DiMaggio: The immediate goal is to successfully promote ‘Fly Away’ and the accompanying music video (out on VEVO on November 19th at midnight). And to secure more funding. We’ve been able to accomplish an incredible amount at a fraction of the cost of equivalent production from major labels, but this all still costs money. I’d like to secure enough funding to fully accomplish my goal of not only providing independent artists in all pockets of the field, from audio to visuals, with fulfilling work, but also to provide them with more than fair compensation, which is what I feel they deserve. I’ll be finishing up the writing and production process for the rest of the project, leading into the spring. The hope is to release the full project sometime in the late spring, early summer. This will complete what I’d call the official proof of concept for the label. The 5-10 year goal is to build out Passeri’s roster and gift the same level of attention and quality that I was able to provide for myself to other emerging artists.
Many thanks to Peter DiMaggio for speaking with us. Find out more about Peter DiMaggio on his Instagram, TikTok, Facebook, and Spotify.
