Discover 209 vintage 1940s era musicians and bands available for hire in Windsor, Ontario, Canada, with 633 reviews from real clients averaging 5 out of 5 stars. Find swing bands, wartime entertainers and close harmony singers to create authentic 1940s atmosphere.
Of the 209 suppliers listed here, 5 are based within 30 miles of Windsor. The other 204 are willing to travel there.
Also covers suppliers based in Detroit, Auburn Hills, Farmington Hills and Shelby.
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1920s Era Musicians & Bands in Windsor
1930s 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 1940s era musicians and bands in Windsor currently range from about $240 to $3,200+ depending on group size and performance duration. The average cost of $800 reflects the specialist expertise authentic period entertainment requires. Contact the supplier you like for an accurate quote.
Based on 46 enquiries for 1940s Era Musicians & Bands at events in Canada, made through this site in the last two years. Updated 18 October 2026.
Mondo Kane
"Always makes me smile when I hear that Mondo Kane style!"
Eugene Mann saxophonist and Wind Synth
"Eugene Mann did an amazing job for my private proposal event. I would recommend Eugene for any kind of event though! He has the skills and experience you want when booking a professional. He is an amazing musician and extremely nice person. He took the time to make sure everything was perfect for the event and nailed it."
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."
All Of Me
"The All of Me show was outstanding, one of the best performances I've seen, Paul Gordon and the band outstanding, his tap dancing super, You don't want to miss it."
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"
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."