Browse 156 professional 1930s era musicians and bands available in Windsor, Ontario, Canada, backed by 482 reviews from real clients and an average 5 out of 5 star rating. These swing bands and jazz ensembles bring authentic vintage entertainment to weddings, parties, and corporate events.
Of the 156 suppliers listed here, one is based within 30 miles of Windsor. The other 155 are willing to travel there.
Also covers suppliers based in Shelby.
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1920s Era Musicians & Bands in Windsor
1940s Era Musicians & Bands in Windsor
1950s Era Musicians & Bands in Windsor
1960s Era Musicians & Bands in Windsor
1970s Era Musicians & Bands in Windsor
1980s Era Musicians & Bands in Windsor
1990s Era Musicians & Bands in Windsor
2000s Era Musicians & Bands in Windsor
Vintage Themed Bands in WindsorRates for 1930s musicians in Windsor typically run between about $300 and $3,300+, with most professional acts averaging $850 for standard performances. Solo performers and small combos typically fall at the lower end of this range, while full swing bands with horn sections command premium rates. Factors affecting pricing include performance duration, ensemble size, and any special song requests or arrangements. Contact the supplier you like for an accurate quote.
Based on 22 enquiries for 1930s Era Musicians & Bands at events in Canada, made through this site in the last two years. Updated 18 October 2026.
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."
Elegant Piano: Cocktail, Jazz & Pop
"A wonderful experience with Jay. He was so responsive when we first contacted him about our event in Stonington CT (a birthday party for my mother with approx. 40 guests at the La Grua Center), and his repertoire spanned all of the types of music were were looking for (jazz, classical, some show tunes). His playing was just so lovely at the event. A pleasure to meet him and have him join this event. My mother was so thrilled and it made her birthday very special. Many thanks to Jay. Highest recommendation."
Gary Strickland
"Gary has done a few events for me as I am a club advisor to students in college. I would say he is all about performing arts, except for the fact that he is just as good with customer service, and interactions on a business level! If he says he'll do something, he follows through with absolute professionalism.
Mr. Strickland has been a solo performer on the trumpet, a singer, an EMCEE, a set designer , a professional photographer and crowd pleaser.
Should anything unexpected happen, he has the experience and sharp reactions to handle a burgeoning situation without a hitch.
I wish I had the time to simply listen to Gary perform outside of the venues for which I have hired him.
Maureen Vendeville
Professor, ESL
Faculty Advisor National Technical Honor Society"
Efrayim Fischbacher
"I'm a professional I respect the music. I've never signed anything like this before."
Jazz Hutch & Friends
"A nice voice and a very understated and carefree delivery. Not enough cats can just Fred Astaire their way through a song."
Good Co
"We hired Good Co for our 1920's themed holiday party. They were extremely flexible and accommodating, especially when we asked if they would follow our leadership around the office as they gathered people for the party. Awesome talent, great at judging sound vs space. Our office is pretty echo-y and loud, but they found the right balance immediately. Definitely keeping on the books for next time!"