Artist Glimpse: Ryan Cassar
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When the 14th Annual CMAOntario Awards wrapped up at Port Credit Memorial Arena on May 31, 2026, the trophy for Musician of the Year went to a man living a remarkable double life. To Ontario’s top country artists, Ryan Cassar is the elite session player holding down the groove on major festival stages and in quiet tracking rooms. But by day, he is a dedicated full-time educator, molding minds in the classroom before packing his gear for weekend runs. With summer festival season in full swing, Glimpse sat down with Cassar to discuss his recent win, balancing the classroom with the road hustle, and how a life built on mentorship is preparing him for his next great chapter.
Rob Aguiar: When they called your name for Musician of the Year at Port Credit Memorial Arena, what was the very first thing that went through your mind?
Ryan Cassar: The first thing that went through my mind was “YES”! I was psyching myself up so much for it that when it happened I was so ecstatic. Elyse Saunders and I had a conversation a few days before and she told me to manifest it like she did her win in 2024 and it all fell into place.
RA: How do you mentally and physically shift gears from the energy of a classroom on a Friday afternoon to a high-energy country festival stage or a late-night tracking session over the weekend?
RC: Honestly, I find it easy to shift gears since I teach music at a high school. With school concerts and lessons I constantly try to paint a picture to the kids of my life so they can embrace that energy. The win for me was a win for them.
RA: If you could raid anyone's record collection for inspiration—or book a dream session with any artist, past or present—who is at the absolute top of your list?
RC: If I was to book a dream session it would definitely be with a few different artists, namely: Albert Lee, Peter Gabriel, Jeff Beck, The Beatles, Paul Simon, Billy Strings, Led Zeppelin, and the list definitely goes on.
RA: Is there a particular guitar in your collection that instantly feels like home in your hands? What is the story behind it, and why is it your go-to for emotional honesty?
RC: For me my tuxedo (white and black) Esquire is the guitar for me. I got it off of Facebook. I traded my Gibson SG for it. People don’t know that it’s a fake. The story from the guy was he got it from a pastor who had made it. I like to think it has some religious mojo.
It’s my go-to because it feels so good in my hands. I’ve received many compliments about the look and sound of it. Funny story, when I first brought it home, my dad didn’t understand the whole “relic craze” to make your guitar look old, so the first thing he said was “why did you buy that piece of s**t”.
RA: As you and your wife prepare to welcome your first child, how do you see this busy educator-musician dynamic shifting? Do you think the legacy of the instrument will naturally carry over into fatherhood?
RC: I find that with anything we’ve come across in our relationship it will be dealt with constant conversation and understanding. I know that I have different responsibilities and a different role now as a father. Any couple who has a newborn has to jointly put the time in at the beginning, but eventually we can afford ourselves time to continue the things we love. I do see things being more selective in the beginning with what gigs I choose. I’m ultimately just happy that he’s due in September leading into the winter gig lull and not being born in peak festival season.
I of course see the instrument passing over into his hands. I would love for him to discover music and fuel a passion for it, as it did wonders for me. It would be excellent to have another person in the family to pass gigs that I can’t do haha.
RA: What advice would you give to a younger player who wants to do what you do—playing on records, performing live, and staying in love with the craft?
RC: My advice would start with the obvious words that I say to my students, “PRACTICE, PRACTICE, PRACTICE”. Learn all your chords, scales, modes, arpeggios etc. This will provide you the dexterity and knowledge on the range of your instrument. Start learning solos from musicians that are better than you. You will then begin to foster a good working knowledge of licks to be able to use. I also recommend an excellent book by Molly Gebrian “Learn Faster, Perform Better”, it discusses learning music and its relation to brain science. It talks about how we can improve musical memory and song retention. Lastly, I will throw out the cliché “get out there and play with everybody and anybody”. I think attending festivals/writers rounds and making your presence known is important as well so you can start getting calls.
I have always maintained this M.O in my career…”When you get the opportunity, give them and yourself no excuses at all, learn the material and nail the show”. These are words I live by and it has done me well in my career. Nothing speaks louder than your reputation and that's all we have, as musicians, in this world.
Whether he is grading papers, anchoring a roaring festival crowd, or preparing for the ultimate role of fatherhood, Ryan Cassar is redefining what it means to be a working artist in Ontario. He measures his success not just by the trophies on his mantle, but by the people he elevates—both on the stage and in the classroom. With a packed autumn schedule on the horizon, Ontario’s country music community is lucky to have him in the groove.
