A Chat with Drew Freeland (29.01.26)
Drew Freeland’s ‘Trouble’ lands with raw honesty, a song born from the final months of a five-year relationship. Her smoky, unpolished vocals carry grit and tenderness, drawing listeners deep into the emotion. We caught up with Drew Freeland to discuss all things music below.
OSR: Can you tell us about your journey from Virginia to Cincinnati and how it’s shaped your music?
Freeland: I think my journey from Virginia to college in Pennsylvania to Cincinnati, where I’m currently living, has allowed my songwriting and voice to develop through life experiences. I was lucky enough at school in PA (Lafayette College) to take a songwriting class they happened to offer my sophomore year, and I think since then my writing and music has grown with my life experience and learnings over the years. Once I got to Cincinnati and was working full-time at a 9-5 at Johnson and Johnson MedTech, I was continually pulled back towards music and writing. Living in Cincinnati since 2021, I’ve experienced the most life changes I’ve ever experienced, and naturally, that’s going to impact my music, lyrics, and the emotions I’m conveying through my songs.
OSR: Your new single ‘Trouble’ is raw and personal. What was the writing process like?
Freeland: ‘Trouble’ was one of those songs I wrote in about 15 minutes. I came back after running bleachers across the street from my house and was feeling really good, on a high from the workout, and it just came out so naturally and with such ease. I was also in the thick of a 5 year relationship, and I feel like it was this moment of clarity and articulation of the situation that we were in that I hadn’t been able to verbalize before, in general, let alone in a song. Once I had the foundation of the song, I came back here and there and added the intro section and refined the nuances of how I sing it to get to where it is now.
OSR: You’ve described ‘Trouble’ as your Johnny Cash song. What does that influence mean to you?
Freeland: Johnny Cash is an icon from my childhood growing up in southwest VA. He was always on in my grandpa’s house growing up, and he was such an honest and comical storyteller. I love the range of his voice and the deep, resonant tone he uses at times in his music, and I’ve tried to incorporate this into my songs as a female because I have the ability to tap into that lower register. I think with ‘Trouble’ specifically, it tapped into that sassy, punchy style of writing Cash uses in some of his songs and coupled with the lower register of my voice, I labelled it my Johnny Cash song with an edge of the Janis Joplin grit.
OSR: How do you approach blending elements of country, folk, rock, and blues in your music?
Freeland: I’m fortunate to have a voice that can carry different genres, so for me it’s not really about sitting down and writing a “country” song with elements of folk, rock, and blues; it’s about writing what I feel. Whether I start with a chord progression or a vocal melody or even just a concept for a song, I let the natural pull of what I feel guide me in the direction of the song. Once I’m in the studio, my goal is to let my vocals and lyrics drive the song and be complemented by whatever instrumentation is added in the studio. This is the process of getting to the final version that is released. Some songs tend to have more of a pull towards blues, rock, or folk, and I think this is really evident in the final product.
OSR: Who were some of the first artists that inspired you to pick up an instrument or write songs?
Freeland: I’m a huge Fleetwood Mac fan, and they have been an inspiration for me all my life, especially Stevie Nicks. Back when I was first learning guitar, life got really busy with sports, and I had to stop taking lessons. At the time, Taylor Swift had just released ‘Love Story’, and chords and instructions were becoming accessible on the internet. My second-oldest sister, Haley, printed out the chords and said, “learn it”. From there, the world was my oyster, and included lots and lots of Taylor Swift through my elementary and middle school days. I was also fortunate enough to be introduced to all kinds of artists growing up, whom I pull an incredible amount of inspiration from, including Jim Croce, Carol King, Aretha Franklin, Shawn Mullins, Five for Fighting, Van Morrison, Bonnie Raitt, John Prine, and the list goes on.
OSR: How do you balance vulnerability and strength in your songwriting?
Freeland: What a great question. I think first and foremost, songwriting has primarily been a therapeutic practice for me to express how I’m feeling, and it’s been something I’ve leaned on throughout my life. It really just depends on the song and what emotion I’m trying to convey. For ‘Trouble’, when I sat down to write it, I was feeling strong and confident, while obviously struggling to figure out the next steps in a relationship. I think the way it came out was almost a comedic relief for where my life was, and it was this song I tethered myself to get through the last few months and make the decision to leave. This song saved me in a lot of ways, and I think that’s why there’s so much strength conveyed in this song.
OSR: What role does storytelling play in your music, and how do you decide which stories to tell?
Freeland: I think when I feel inspired by people, situations, and emotions in life, that drives a lot of my songwriting. But sometimes I sit down, and I have a hook or a chord progression I like, and I build the story around that, whether it’s personal to me or not. But I do think there’s a part of myself in almost every song I write.
OSR: Can you walk us through your process in the studio with Joe Bianchi for this track?
Freeland: With ‘Trouble’, we used a live tracking approach, so the bass and drums were recorded live with a band. From there, I overdubbed acoustic guitar, lead vocals, and background vocals. Then we brought in Alex Johnstone, who nailed the mandolin. The final piece before mix was Paul Patterson overdubbing the fiddle throughout the song as the final touch before sending the song to mix.
OSR: How do you translate your onstage energy into a recorded performance?
Freeland: I think recording the drums and bass in the live studio setting really helped in terms of singing to the instrumentation because they felt alive and real. Additionally, all of the musicians did an amazing job of bringing the right energy to the song to hone in on the energy of the tune.
OSR: Looking back on your career so far, what’s a moment that defined you as an artist?
Freeland: I think as a musician and singer-songwriter, there are many moments throughout a career that define you as an artist, and it’s a continual process of learning who you are as an artist and branding yourself based off that. I think ‘Trouble’ is a very special moment for me as an artist because I still feel very close to the song, and I did throughout the process of bringing it to life. I think there’s so much of my personality in this song, and I’ve never released anything like it, so it’s a very special release for me!
Many thanks to Drew Freeland for speaking with us. Find out more about Drew Freeland on her official website, Instagram, and Spotify.
