Timber Masterson Gets His Heart Broken Every Time In Jenni’s Song

The Toronto troubadour shares a home-made video for his debut single.

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Tim “Timber” Masterson explores a world of heartache on his debut single and home-made video Every Time (Jenni’s Song) — showcasing today on Tinnitist.

The first preview of his upcoming album Heavens So Dark, Every Time (Jenni’s Song) is everything you could want from a folk-pop song. An acoustic guitar passage emerges from steady percussion before piano and electric guitar enter and complement seamlessly. Then, Masterson’s gentle opening vocals — “Every time you take me far away / And every time I feel you come this way / Babe, I feel you each and every day” — tell a story of the ups and downs, uncertainties, and evolution of an intimate relationship. His lyrics are both heartfelt and personal, revealing a sense of longing that remains present throughout the album.

Masterson says, “These days I’m writing from a much different place; a place of joy and hope, huge for me and a big change which I’m thankful for. It’s great when the melodies pour out of you and connect, resonate from a pure place. It’s wonderful when one finds a new muse to be inspired by.” She joins other influences such as David Sylvian, Red House Painters, The Blue Nile, Aimee Mann, Shawn Colvin and Canadian Leif Vollebekk. Explains Masterson: “I’ve always dug stuff that was a little left of center, have always appreciated those that take the road less travelled.”

Masterson has part of Toronto’s music scene for as long as he could remember. His earliest memories came from listening to his mother play the family’s 100-year-old Steinway piano, an instrument he now uses to compose his own songs. As a young adult, Masterson was a part of the city’s art party scene where he was inspired to make his own music. Heavens So Dark is Masterson’s first attempt at a full album. It’s the result of his artistic journey up to this point — playing piano at the Roosevelt Hotel in Hollywood, guitar at The Viper Room in Los Angeles, and organizing warehouse jams in Toronto and New York.

Masterson plays piano and guitar by feel, allowing his emotions to guide his compositions. “My first instrument is the piano, but I picked up the acoustic guitar during a play I was on tour with in Newfoundland. I told myself I was going to teach myself to play, and I did. I think not having structured music lessons has helped me as an artist — I play what I feel, not often what is structured or has a predictable framework. I often experiment with different tunings on the guitar.”

His work involves collaboration with producer Barry Haggarty, who “fills in the gaps, often quite beautifully,” to his demos. This charming quality persists through the six tracks, even when they explore different genres. The album crosses into sophisti-pop with Say We’ll Go Away and soft rock in Story To Be Told, while Waterfront Lullaby is a dance track incorporating synths, saxophone, and flute.

Watch the video for Every Time (Jenni’s Song) above and sample more sounds from Timber Masterson below.