Anthony D’Alessandro Quartet feat. Benny Benack III | June 19th, 2025

Music & Entertainment
June 19th, 2025. 7:00 PM
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Jun 19, 2025
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Anthony D’Alessandro is a pianist, composer, arranger, and bandleader based in Toronto, Canada. Hailed by WholeNote Magazine as a pianist with a “natural feeling for swing and groove” and “scintillating technique,” he has performed in many notable clubs, concert halls, and jazz festivals worldwide, including the Montreal International Jazz Festival, the Teatro Nescafé de las Artes in Santiago, Chile, Birdland Jazz Club and Smalls Jazz Club in New York City, and Koerner Hall in Toronto. He regularly performs alongside a “who’s who” of Canada’s top jazz musicians including Caity Gyorgy, Neil Swainson, Terry Clarke, Pat LaBarbara, and Ernesto Cervini, and has performed or toured with many notable NYC-based musicians, including Benny Benack III, Summer Camargo, Alexander Claffy, and Joseph Farnsworth.

D’Alessandro’s debut full-length album Searchin‘ (2024), featuring NYC-based trumpeter and vocal star Benny Benack III, debuted to critical acclaim, being called an “uplifting and feel-good jazz record” by Paris Move, and a “gem of an album” by Jersey Jazz Magazine. His composition Tune for Monty was selected for CBC Music’s prestigious “Songs You Need to Hear” list in May 2024.

D’Alessandro’s music has taken him throughout Canada, the United States, South America, and Europe. He has performed at many of Canada’s most prestigious venues, including Koerner Hall in Toronto, and at all of the major Canadian jazz festivals across the country. He has also toured across Chile under his own name, performed at jazz clubs and festivals across the United States, and presented his compositions at the Casalmaggiore International Music Festival in Casalmaggiore, Italy. D’Alessandro frequently tours and records with three-time JUNO award-winning vocalist Caity Gyorgy, having played on her most recent JUNO-winning album Hello, How Are You?

D’Alessandro has spent time living and studying in New York City under master pianist/organist Mike LeDonne, and holds a Bachelor of Music degree from the University of Toronto.

Benny Benack III

Benny Benack III is a trumpeter, vocalist, and rising star in the jazz world. Known for his dynamic performances and unique ability to seamlessly blend powerful trumpet playing with expressive vocals, Benny has quickly become a standout figure on the scene. He has headlined at clubs and festivals worldwide and is celebrated for his albums such as Third Time’s the Charm, which reached #2 on the JazzWeek International Radio Charts in 2023. A finalist in the 2014 Thelonious Monk Competition and a third-place winner in the 2021 Sarah Vaughan Vocal Competition, Benny continues to earn acclaim for his double-threat abilities as both a trumpet virtuoso and a captivating vocalist. His engaging stage presence and infectious enthusiasm have made him one of the most in-demand touring artists in jazz today.

Joining Anthony and Benny will be Ernesto Cervini on drums and Jonathan Chapman on bass