NYVC Singer Spotlight: Sasha Montefiore
Posted Wednesday, May 27th 2026 by Jamie Kaufman
NYVC’s Jamie Kaufman had the pleasure of interviewing actor, writer, filmmaker, and singer Sasha Montefiore about rediscovering his love for singing after years away from music. Sasha shares the influences that shaped him, the challenges he's faced as an artist, and the mindset that continues to fuel his creative journey.
How did you discover your passion for singing?
I used to sing a lot as a child. My parents would never allow me to own a phone, but they did let me have an iPod Touch. Because of that, I listened to a lot of music from a young age, particularly older artists such as Bowie, Cohen, and Elton John, as well as modern artists whose music was very simple, like James Blunt, who sang and played guitar, nothing more.
I remember seeing Ed Sheeran perform "The A Team" on television in 2011. I was eight years old, and it was one of the most incredible songs I had ever heard. Around that same time, I also discovered "Daydream Believer" by The Monkees. I've never forgotten either of them.
At school, I was part of an elite choir made up of only five boys at the boarding school I attended in England. I loved it. But when I went to high school at age 13, I stopped singing. I simply forgot about it. I think a large part of why I stopped was that, in an all-boys boarding school with a very toxic culture of masculinity, singing was often seen as weak or pathetic and was ridiculed by other students. So I suppose I stopped out of fear, but my love for singing never faded.
What’s something recent or exciting in your singing journey?
"Exciting" can be very subjective, but returning to singing last November after such a long time away has been incredibly exciting for me. I'm also incredibly grateful to have found Laura Castrillón, my singing teacher, who has been wonderful, kind, and patient. As much as I would like to sing the way I used to, I've learned that growth takes time. The most important thing for me is connecting to the song and feeling the emotion behind each line, which is something I especially enjoy as an actor.
What is an interesting or funny fact about you?
I am primarily an actor, writer, and filmmaker, but I also make music in my free time, composing and recording pieces on the piano. Although I don't release any of it, and perhaps never will, it's a creative outlet that I need in my life. Creating music has become essential to who I am because nothing affects me emotionally quite like music does, perhaps not even film. That said, music remains a vital part of filmmaking and storytelling, which is one of the reasons it continues to inspire me so deeply.
What led you to studying at NYVC?
Singing is an important skill for an actor to have. I want to be able to audition for musicals as well as drama. I also missed singing a lot and did not feel whole without it.
Who or what are your biggest musical influences?
As a child growing up in England, I heard a lot of older music at home and in the car, and it inspired me deeply. This included Elton John’s "Crocodile Rock," David Bowie’s "Five Years," Kenny Rogers’ "The Gambler," John Denver’s "Annie’s Song," James Blunt’s "Wisemen," and songs like "Scarborough Fair" by Simon and Garfunkel, as well as music by The Monkees and The Kinks, among many others. Michael Jackson was also frequently played in my house.
As I grew older, I explored many different genres, from hip hop to dream pop, folk, and classical, all of which I still listen to every day. The artists who inspire me most today, and whose music I try to emulate, are Gregory Alan Isakov, whose song "Berth" is a favorite, Leonard Cohen, Lana Del Rey, and Zach Bryan.

What styles of music do you sing?
I tend to sing folk rock because it connects with me most emotionally.
What is one piece of advice you’d love all singers to know?
For artists in any form, it is about failing, failing, and failing again. If you are afraid of failure, you will never take risks, and as a result you will never succeed or create anything worth creating. You must embrace the possibility of looking stupid and failing. It is the only way.
What is the biggest challenge you’ve faced as an artist?
Getting out of my head. Being far less self-conscious and analytical, and focusing on the moment rather than what everyone else is doing. Taking risks, however ridiculous or outrageous, and pursuing your dream ferociously, with complete focus, drive, and obsession, because that is the only way you are going to get it.
What has been your greatest victory as an artist?
So far, my greatest victory is that I am just as motivated, if not more so, than when I first decided to become an actor.
Where can people find more about you and your music?
Although I hate social media and refuse to have the app on my phone, the best way to find me is with Instagram @sashamontefiore. Thank you!
Jamie Kaufman
Jamie Kaufman is a professional singer and dedicated vocal coach with a passion for helping singers discover their voice. With a Bachelor of Music in Vocal Performance and a Minor in Music Education, as well as a Master of Arts in Teaching from The University of The Arts, Jamie combines extensive training with a genuine love for helping students reach their full musical potential.
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