Discover 126 professional crooners available for hire in Windsor, Ontario, Canada, backed by 269 reviews from real clients averaging 5 out of 5 stars. These smooth jazz vocalists bring sophisticated entertainment to weddings, corporate events, and private celebrations with prices starting from $180.
Each performer offers their own interpretation of classic crooning style, from vintage swing standards to contemporary smooth jazz arrangements. The average booking price locally is $700, covering solo performances with piano or backing tracks, consultation on repertoire selection, and coordination with your event schedule.
Of the 126 suppliers listed here, one is based within 30 miles of Windsor. The other 125 are willing to travel there.
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Professional crooners in Windsor, Ontario, Canada specialize in delivering the smooth, intimate vocal style that epitomizes sophisticated entertainment. These talented performers bring decades of musical heritage to modern events, combining technical excellence with the emotional connection that makes crooning such a compelling art form.
Smooth jazz vocalists in your area offer diverse repertoires spanning the Great American Songbook, contemporary jazz standards, and modern crooner interpretations. Many performers provide flexible accompaniment options, from solo piano arrangements to full backing tracks, adapting their presentation to suit intimate gatherings or larger celebrations. The versatility of local crooner singers allows them to create perfect ambiance for cocktail receptions, dinner entertainment, or featured performance segments.
Hiring a crooner singer in Windsor typically costs between $180 and $2,000+, with most bookings averaging $700 for professional performances. Local pricing reflects performance duration, accompaniment requirements, and the performer's experience level. Solo crooner performances with piano or backing tracks offer excellent value for intimate events, while full band arrangements are available for clients seeking premium entertainment experiences. Most performers in your area include repertoire consultation and event coordination in their standard booking fee.
The average price for Crooners available in Windsor, Ontario, Canada is $700 (CAD). Above you will also find a budget price and high end price. Contact the supplier you like for an accurate quote.
Based on 83 enquiries for Crooners at events in Canada, made through this site in the last two years. Updated 15 October 2026.
Vintage Vocals - Steve Elmore
"This is a REALLY late review but I want the world to know what a great performance Steve puts on. He was a monthly performer at Shelby Crossing Senior Center when my mom was a resident and I enjoyed him so much that I asked him to play at my mom's funeral memorial. Everyone in attendance loved it as they knew my mom and dad were avid dancers and this was just the perfect sendoff."
Kevin Krieger saxophonist
"Kevin was amazing! We hired him to help celebrate my parents 50th wedding anniversary and they had a blast. Kevin played a broad range of music, entertaining the kids and grandparents all the same. Definitely recommend!"
Rick Holland's Uptown Society Orchestra
"All Music Review
Thom Jurek
The title of this set is an apt one. While much of the music presented by the Rick Holland-Evan Dobbins Little Big Band, it hearkens back -- in terms of its sophistication, confidence and outright jazz literacy, not nostalgically -- to an era when progressive jazz, and big bands (this one numbering 10 pieces) flourished on the scene. This is one sophisticated outfit. Featuring the arrangement and compositional skills of Brent Wallarab, Jim Martin, Bill Dobbins and Kerry Strayer, this band struts out the tradition and make some joyous, complex, and elegant music that reflects its own unique identity. The résumés of all these players are impressive and reflected in the confidence of the date. It opens with "SUNY-Triangle," a Martin composition that works its artful sleight-of-hand over Antonio Carlos Jobim's "Triste." Martin uses the rhythmically complex samba and drapes some tough, knotty twists and turns over it. The intro is a beautiful and raucous wake-up call, while the head of the tune, with its staggered entrances and exits -- including some fine soloing by John Viavattine on tenor and John Nyerges on piano -- give this tune a unique identity. "Creature Comfort" is a beautiful mid-tempo ballad by Wallarab with edgeless yet multi-dimensional dissonances written into its harmonics. It swings beautifully and includes a fine, punchy solo by tenorman Glenn Cashman. Besides the originals, there are some fine readings here as well. There's Wallarab's arrangement of Duke Ellington's "Black and Tan Fantasy" that's a thoroughly modern exercise losing none of Ellington's humor or rhythmic complexity. Likewise, Gerry Mulligan's haunting, wee-hours, "Night Lights," is given expert treatment here by Strayer, and Dean Keller's baritone saxophone playing combines Mulligan's sense of lyric and Ben Webster's sense of time. In Time's Shadow reveals that innovation need not sacrifice accessibility or swing. It is convincing evidence that the big band form is alive, well and full of surprises."
John Amato
"I am a volunteer at Walden and we all enjoyed your show today
Thanks so much for entertaining the residents
It was terrific.
We look forward to seeing you again"
The Rick Levine Band
"Fantastic Band! Rick is easy to work, dance floor was full all night long. Guests are still talking about how the Rick Levine Band helped make my event a success! Thanks."
Jerry Armstrong Tribute Artist
"Jerry did an amazing job! He was on time and brought all of his equipment, he knew all the songs and sang them very well. He interacted with the crowd, he was very friendly and funny. I would definitely hire him again. -Rachel W, Tinley Park, IL"