Discover 115 professional 1920s era musicians and bands available for hire in Windsor, Ontario, Canada, with an average rating of 5 out of 5 from 307 reviews from real clients. These vintage jazz ensembles focus on authentic 1920s entertainment and Great Gatsby-style performances.
All 115 suppliers listed here are willing to travel to Windsor. The nearest is based in Cleveland, United States, 88 miles away.
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1930s 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 1920s era musicians and bands in Windsor range from $300 to $4,000+, with an average booking cost of $950. Pricing typically reflects the size of the ensemble, performance duration, and additional services such as period costumes or vintage equipment. Smaller jazz combos represent excellent value for intimate gatherings, while larger orchestras provide spectacular entertainment for major themed celebrations. Contact the supplier you like for an accurate quote.
Based on 788 enquiries for 1920s Era Musicians & Bands at events in every location, 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."
The Kensie Jazz and Dance Band
"Perfect Jazz Band!
Secured The Kensie Jazz Band for our 30th Anniversary corporate event. From start to finish they were perfect. Perfect background music while guests are engaging in the social circuit. Perfect background music while being seated and served for dinner. The band can adjust their sound level to your preference. They play a range of music. A live band is a classy touch and adds ambience to any event rather than a standard DJ. It is a completely different vibe. Nice group of people! Good pricing as well. Thank you!"
Crook & Company
"Robert and I are so over the moon grateful for the way Crook & Company graciously serenaded us and our guests for our wedding. You all did a phenomenal job with every detail. You were all professional, had amazing energy and extremely talented! You guys made the night perfect! I will definitely recommend your band in the future."
Leah Hinton Band
"Leah and her guitarist Noe sang/played at my wedding ceremony and reception and added SO much to the romantic yet playful ambience I had going on. Her voice is absolutely gorgeous and flexible, accommodating jazzy/soul numbers to indie and pop numbers alike. She was extremely communicative and helpful in choosing songs, playlists and had great suggestions that made my wedding absolutely perfect
Thank you so much Leah and Noe!!"
Andrew Thielen Big Band
"WE were so glad we found Andrew Thielen Big Band. They are a real band that has been together for over twenty years perfecting their music, showmanship and dazzling variety of music that kept our dance floor jammed. WE almost got swayed into one of these chain bands called Empire something where they throw together bands for one night until we figured out you cannot be a 3 piece band one week and a 12 piece band the next. WE wanted a real band where the band leader has had repeat performances for the most discriminating buyers for years. Every age, everyones taste in music and our twenty something wedding party had the time of our life. Call them now for sensational singers, instrumentalists and organization."
Texas Gypsies
"In a word... FABULOUS! These guys gave us just the sound we needed for our fun Prohibition-theme wedding. It is now two weeks later, and all we keep hearing is "Man, that band was fantastic!" They are worth the asking price (which is very reasonable to begin with!) Steve Curry is a great guy and very easy to deal with. I would recommend them without any reservations."