Get ready for an extraordinary evening of jazz brilliance as the Anthony D'Alessandro Quintet takes the stage, joined by the phenomenal Benny Benack III. This headline performance promises exceptional artistry and unforgettable melodies, marking it as a true highlight of JazzFest Regina 2025.Kick off your weekend with an incredible evening at the Lazy Owl. Enjoy a night filled with exceptional performances, great energy, and unforgettable music. Make sure to grab your advance tickets for the best deal!
Friday, June 20th
Time 7:30 PM
Location: Lazy Owl, 3737 Wascana Parkway, Riddell Centre, University of Regina
Tickets: $35 Advance | $40 at the Door
Ticket pkgs available:
All concerts – excludes Brunch/Concert – $225
All concerts – includes Brunch/Concert – $275
Anthony D’Alessandro is a pianist, composer, arranger, and bandleader based in Toronto, Canada. Hailed by the 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 around the world including the Montreal International Jazz Festival, the Teatro Nescafé de las Artes in Santiago Chile, 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 Joe 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 the 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.
D’Alessandro’s music has taken him throughout Canada, Chile, the United States and Europe. He has performed at many of Canada’s most prestigious jazz festivals and concert venues including Koerner Hall in Toronto, the Ottawa Jazz Festival, and the Vancouver Jazz Festival, among others. He has also performed at the International Glenn Miller Festival in Clarinda, Iowa, the Snowbirds Extravaganza Festival in Lakeland, Florida, and presented his compositions at the Casalmaggiore International Music Festival in Casalmaggiore, Italy.
D’Alessandro frequently works as the pianist for two-time JUNO award winning vocalist Caity Gyorgy, and has toured Canada from coast to coast as part of Gyorgy’s acclaimed quartet. This group made their Koerner Hall debut in April 2024 and has performed at every major jazz festival in the country. His playing can be heard on Gyorgy’s latest release “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 where he studied under award winning pianists David Braid, Mark Eisenman and David Restivo.
BENNY BENACK lll
“Anthony has a natural feeling for swing and groove, scintillating technique and a penchant for such feel-good pianists as Erroll Garner, Oscar Peterson, and Monty Alexander.”
— Steve Wallace for WholeNote Magazine
By age 33, Emmy-nominated trumpeter and singer Benny Benack III has proven to be that rarest of talents: not only a fiery trumpet player with a stirring command of the postbop trumpet vernacular in the vein of Kenny Dorham and Freddie Hubbard, but also a singer with a sly, mature, naturally expressive delivery in the post-Sinatra mold, performing standards and his own astute songs with a thrilling sense of showmanship. This duel-threat ability was recognized by the 2025 Downbeat Readers Poll where he won the category of Rising Star Male Vocalist, and placed #8 as a Rising Star Trumpeter as well. His superb intonation and bracing virtuosity enable him to handle astounding feats of originally composed vocalese (complex solos with written lyrics). On top of it all, he’s a highly capable pianist as well.