Noteworthy

Tony DeSare performs with infectious joy, wry playfulness, and robust musicality. Named “Rising Star Male Vocalist” by DownBeat, he has appeared everywhere—from jazz clubs to Carnegie Hall—and headlined with more than 100 symphony orchestras, including The Cleveland Orchestra, New York Pops, San Francisco Symphony, and Chicago Symphony. An award-winning composer and Billboard-charting artist, he is also the creator of the much-loved Song Diaries series, which began during the pandemic and has grown to include more than 300 performances shared worldwide.

Returning to the TSO, DeSare will lead The Billy Joel Songbook and bring the iconic music of Billy Joel to life in a power-packed performance of the singer’s chart-topping hits. Ahead of his highly anticipated performances, he shared his thoughts on music, travel, and the moments that have shaped his artistry.

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I make a conscious decision that my music serves a purpose of being positive, optimistic, and romantic. Two people can sit side by side in a concert hall, holding completely different ideologies, and for a couple of hours they are united—having the same human reactions, sharing the same joy. That sense of connection is what I strive for every time I perform.

During the pandemic, I began recording a song every day. What started as a way to fill the silence became something much bigger: a community. I received a message from someone in England who told me that my daily videos gave him something to look forward to and kept him going. In that moment, I realized the power of what I was doing. 

You see numbers, comments, likes—but you don’t really grasp how deeply you can affect someone until you hear a story like that. Those first 100 days of the Song Diaries remain vivid to me. People still come up after shows and tell me they discovered me during that time, and it has become an unexpected, special chapter of my career.

Of course, the balance isn’t always easy. Performing is the joy; travelling is the challenge. Life on the road has no routine, and family time can be hard to protect. But I feel nothing but gratitude that I get to do this for a living, especially after everything shut down. Time at home gives me the space I need to create—sometimes that means walking around New York during my residencies at The Carlyle, simply observing and letting inspiration refill the tank.

One of the toughest moments in my career came when my record label was dissolved. I had worked for years to get signed—this was before streaming, when the only way people could discover you was through CDs in a store. Suddenly, I had to start over, reinventing myself as an independent artist. But that pivot ultimately led me to orchestra pops, which turned out to be the perfect fit. I had grown up playing violin, arranging music, and loving the American Songbook. To stand in front of a world-class orchestra now—singing Sinatra, Gershwin, or Billy Joel—is an extraordinary privilege, and I love every aspect of it.

Frank Sinatra and Billy Joel are the two towering influences. Add Stevie Wonder and George Gershwin, and that’s my personal Mount Rushmore. For piano, Oscar Peterson. For songwriting, Cole Porter. And if I need comfort, I’ll always return to Sinatra. Still, I have guilty pleasures—80s pop, yacht rock, Huey Lewis, and Christopher Cross.

Books can change you, too. For me, it was the Dao De Jing—direct, simple, filled with wisdom about leadership, kindness, and how to live. I come back to it often.

There have been many memorable performances in my life, but Carnegie Hall will always stand out. When I first moved to New York, I couldn’t even afford a ticket to sit in the audience. That place felt untouchable. Then came the night I walked out on that stage with The New York Pops and sang. I’ve been back several times since, but I’ll never forget the first—the feeling that, somehow, I was actually pulling this off.

The show I bring to Toronto is especially close to my heart. The first album I ever bought with my own money was Billy Joel’s Storm Front. This program is my way of treating his music as part of the American Songbook—highlighting the beauty of his lyricism and composition. It’s a labour of love, and I can’t wait to share it.

See Tony DeSare with the Toronto Symphony Orchestra:

The Billy Joel Songbook
Wed, Oct 8 & Thu, Oct 9, 2025
Roy Thomson Hall

Discover where music and life intersect in Intermezzo as we bring you closer to the artists who shape the TSO experience. Keep an eye out for more of these insightful conversations.