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The 4 Best 1920s Era Entertainers for Hire in Windsor, ON

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60 1920s Era Entertainers serving Windsor, ON
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What Windsor Users Say

5-star review

“BEST DECISION EVER” – Hannah C., reviewing Columbus 1920s Era Entertainer Elizabeth Hayes Jazz Review. More reviews

The Gatsby Gang Jazz Band - Jazz Band / 1920s Era Entertainment in Detroit, Michigan Featured vendor banner
The Gatsby Gang Jazz Band - Jazz Band / 1920s Era Entertainment in Detroit, Michigan

The Gatsby Gang Jazz Band

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5.0 (3)
  • Map pin icon Detroit, MI
  • Vendor category icon Jazz Band / 1920s Era Entertainment
  • Travel distance icon 1 mile from Windsor
  • Check mark icon 9 Verified Bookings

Ayodeji B. said “Great evening”

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Louis Pettinelli Entertainment - Jazz Band / 1920s Era Entertainment in Detroit, Michigan Featured vendor banner

This vendor provides virtual services Offers Virtual Services

Louis Pettinelli Entertainment - Jazz Band / 1920s Era Entertainment in Detroit, Michigan

Louis Pettinelli Entertainment

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4.87 (47)
  • Map pin icon Detroit, MI
  • Vendor category icon Jazz Band / 1920s Era Entertainment
  • Travel distance icon 1 mile from Windsor
  • Check mark icon 136 Verified Bookings

Janet H. said “I am extremely please with the band and the and Louis Pettinelli Entertainment. They were timely, professional and played beautifully. I received nothing…”

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Background Jazz Band - Jazz Band / 1920s Era Entertainment in Detroit, Michigan Featured vendor banner
Background Jazz Band - Jazz Band / 1920s Era Entertainment in Detroit, Michigan

Background Jazz Band

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4.85 (9)
  • Map pin icon Detroit, MI
  • Vendor category icon Jazz Band / 1920s Era Entertainment
  • Travel distance icon 1 mile from Windsor
  • Check mark icon 22 Verified Bookings

Diane C. said “My event was held outside, weather was gorgeous, large crowd of 300 spread around the facility and this group's music was perfect! It is clear they enjoy…”

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Jazz Band for Holiday Parties - Jazz Band / 1920s Era Entertainment in Detroit, Michigan Featured vendor banner
Jazz Band for Holiday Parties - Jazz Band / 1920s Era Entertainment in Detroit, Michigan

Jazz Band for Holiday Parties

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0 (0)
  • Map pin icon Detroit, MI
  • Vendor category icon Jazz Band / 1920s Era Entertainment
  • Travel distance icon 1 mile from Windsor

We provide live jazz for Holiday and Christmas Parties!

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Cherie Blondell - Burlesque Entertainment / 1920s Era Entertainment in Columbus, Ohio Featured vendor banner

This vendor provides virtual services Offers Virtual Services

Cherie Blondell - Burlesque Entertainment / 1920s Era Entertainment in Columbus, Ohio

Cherie Blondell

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4.73 (4)
  • Map pin icon Columbus, OH
  • Vendor category icon Burlesque Entertainment / 1920s Era Entertainment
  • Travel distance icon 163 miles from Windsor
  • Check mark icon 5 Verified Bookings

Cheri D. said “I don't know how we got this lucky to find this caliber of talent from Columbus Ohio but we did! Cherie Blondell brought it and with a room full of people…”

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Razzamatazz & Jazz - Dixieland Band / 1920s Era Entertainment in Columbus, Ohio Featured vendor banner
Razzamatazz & Jazz - Dixieland Band / 1920s Era Entertainment in Columbus, Ohio

Razzamatazz & Jazz

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5.0 (14)
  • Map pin icon Columbus, OH
  • Vendor category icon Dixieland Band / 1920s Era Entertainment
  • Travel distance icon 163 miles from Windsor
  • Check mark icon 18 Verified Bookings

Nancy K. said “Always good music. I have booked them in the past too.”

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Elizabeth Hayes Jazz Review - Jazz Band / 1920s Era Entertainment in Columbus, Ohio

This vendor provides virtual services Offers Virtual Services

Elizabeth Hayes Jazz Review - Jazz Band / 1920s Era Entertainment in Columbus, Ohio

Elizabeth Hayes Jazz Review

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4.3 (13)
  • Map pin icon Columbus, OH
  • Vendor category icon Jazz Band / 1920s Era Entertainment
  • Travel distance icon 163 miles from Windsor
  • Check mark icon 9 Verified Bookings

Timothy S. said “The band arrived on time for set up just as planned . Very professional in reviewing the order of events and planning accordingly. Lovely music and vocals…”

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Claudia Sanchez, the Passionate Pianist - Pianist / 1920s Era Entertainment in Pittsburgh, Pennsylvania Featured vendor banner
Claudia Sanchez, the Passionate Pianist - Pianist / 1920s Era Entertainment in Pittsburgh, Pennsylvania

Claudia Sanchez, the Passionate Pianist

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5.0 (7)
  • Map pin icon Pittsburgh, PA
  • Vendor category icon Pianist / 1920s Era Entertainment
  • Travel distance icon 204 miles from Windsor
  • Check mark icon 16 Verified Bookings

Laura D. said “Miss Sanchez was Professional, presentable, and very talented. We will most likely invite her back To our country club again. Our guests enjoyed her very…”

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Hot Club of Buffalo - Swing Band / 1920s Era Entertainment in Buffalo, New York Featured vendor banner
Hot Club of Buffalo - Swing Band / 1920s Era Entertainment in Buffalo, New York

Hot Club of Buffalo

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0 (0)
  • Map pin icon Buffalo, NY
  • Vendor category icon Swing Band / 1920s Era Entertainment
  • Travel distance icon 215 miles from Windsor
  • Check mark icon 1 Verified Booking

Whether you're 9 or 90, The Hot Club of Buffalo makes everyone happy. Dancers love the rhythms. Audiences love the catchy melodies. And everyone has a good time.…

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Quick facts
1920s Era Entertainment in Windsor, ON

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1,249 quotes sent

In the past year, 1920s Era Entertainers have sent 1,249 quotes to event planners

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119th most popular

1920s Era Entertainers rank #119 in popularity out of 545 categories on GigSalad

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5 out of 5 stars

560 1920s Era Entertainer reviews on GigSalad with an average rating of 5 stars

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3 days on average to book

From request to booking, it takes 3 days (on average) to hire 1920s Era Entertainer

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Ontario ranks #2

for 1920s Era Entertainer requests in Canada

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1920s Era Entertainment in Windsor, ON


For black-tie affairs, large corporate events, high-class dinner parties, holiday parties, birthday parties, anniversary parties, supper clubs, or other occasions, bands playing 1920s Musical Entertainment and period music from the roaring twenties can be an excellent entertainment choice. Popular entertainers from this fun-filled decade include Josephine Baker, Al Jolson, George Gershwin, Vaudeville Performers and Harlem Jazz musicians (to name a few). Related searches include Big Bands, Swing Bands, Jazz Bands, Jazz Singers. Start your search by selecting your city above.

Some things to consider when hiring 1920s entertainment is to make sure you listen to audio and watch video clips of the performer/group. This will ensure that you truly do book the best for your next event! Next, you want to get references. Talk to people in the area about the performer and get feedback. Finally, get a contract. Many professional performers require a deposit to secure them at your next event. Make sure to read through the contract carefully before contracting their services for your party. Search for 1920s Era Entertainment in Windsor, Ontario above.

Please note that these 1920s Era Entertainment may also travel to Sandwich, East Windsor, Riverside, River Rouge, La Salle, Lasalle, Grosse Pointe Park, Oldcastle, Ecorse, Melvindale, Tecumseh, Grosse Pointe, St Clair Beach, Saint Clair Beach, River Canard, Grosse Pointe Farms, Harper Woods, Maidstone, Grosse Pointe Woods, Center Line, Pleasant Ridge, McGregor, Riverview, Huntington Woods, Grosse Ile, Emeryville, Redford, St Clair Shores, Essex, and Amherstburg.

Find 1920s Era Entertainment in nearby cities

Detroit Hamtramck Highland Park Dearborn Lincoln Park Wyandotte
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