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79 Oldies Music Groups serving Madison, WI

Featured

MAC Daddy Entertainment

4.64 (11)
21 Verified bookings

  • Waupun, WI
  • Elvis Impersonator / Oldies Music
  • 51 miles from Madison
  • $895 – $1,400 per event

Athena B. M. said “We had Elvis for our Grandmas 97th Birthday - It’s four days later and Grandma is still over the moon!!! ”
Featured

Dan Fester

5.0 (18)
Top Performer
26 Verified bookings

  • Woodstock, IL
  • One Man Band / Oldies Music
  • 71 miles from Madison
  • Starts at $400

Nicole B. said “Dan was so cool! Everyone wanted the night to go on for his performance. ”
Featured

Greg Rogalinski

4.93 (81)
Top Performer
154 Verified bookings

  • Milwaukee, WI
  • Frank Sinatra Impersonator / Oldies Music
  • 76 miles from Madison
  • $100 – $1,000 per event

Stacey M. said “Hiring Greg was the best decision we made to have a memorable engagement party for our daughter. The theme was “That’s AMORÉ” and his Dean Martin/Frank Sinatra was spot on. He was prompt and set up... ”
Featured

Coventry Jones Band/Acoustic

4.90 (31)
Top Performer
65 Verified bookings

  • Milwaukee, WI
  • One Man Band / Oldies Music
  • 76 miles from Madison
  • $100 – $800 per event

Lori W. said “He brought great energy and kept the atmosphere fun from start to finish. It’s impressive how much sound and entertainment one person can create. He had everyone enjoying themselves. ”

Estimate the cost

We’ve gathered average pricing for hiring Oldies Music in your region using data from quotes sent through GigSalad.

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Quick facts for Oldies Music in Madison, WI

3,957 quotes sent

In the past year, Oldies Music have sent 3,957 quotes to event planners.

56th most popular

Oldies Music rank #56 in popularity out of 539 categories on GigSalad.

5 out of 5 stars

There are 2,060 Oldies Music reviews on GigSalad with an average rating of 5 stars.

1.4 days on average to book

From request to booking, it takes 1.4 days (on average) to hire a Oldies Music.

Madison ranks #3

Madison is the 3rd most popular city for Oldies Music requests in Wisconsin.

Popular events

Oldies Music are typically hired for Personal Occasions in Madison, WI.

Wisconsin ranks #15

Wisconsin is the 15th most popular state for Oldies Music requests in the United States.

Past events for Oldies Music in Madison, WI

5 stars isn't enough

Oldies Music

5.0

June 10, 2026

1 hour

I booked Tracey for a senior event at a skilled nursing facility and I couldn't have been more pleased. I never saw the level of resident engagement that she was able to draw out of the crowd. All my residents were singing right along with her for most of the show. I already have residents and staff asking when she will return. Tracey has a wide range of songs, she took time to get to know the residents and played some of their requests. Anyone looking for a great talent can't go wrong choosing her. I will definitely be having come back.
Event total

$115

About booking Oldies Music in Madison, WI

Take a trip down memory lane with some live oldies music! Fill your next event with nostalgic hits from the 1950s, 60s, and 70s. Hire an oldies band or musician to play fun dance music at your wedding reception, prom, corporate event, anniversary, or decade-themed party. Check out the profiles above to find local oldies bands for your special event.

The cost of booking oldies music in Madison, Wisconsin can vary depending on the length of the event, the size of the group, and their skill level. Large party bands with full costumes and years of experience may charge more for their performances but are well worth the price. Contact oldies music acts near you to get a quote customized for your event.

When browsing profiles for Madison oldies music groups, look through photos, listen to audio samples, and watch videos to learn more about their services and style. Then read reviews from past clients to see what it would be like to work with them. When talking with professional oldies groups, discuss important details like arrival times, setup requirements, costume preferences, and any song requests you might have.

Once you find an oldies band or musician to hire, finalize the booking through GigSalad. Our full-service platform makes it easy to book live music for public events and private parties. You can message the performer, confirm the agreement, and make a secure payment all in one place. Every GigSalad booking is protected by our Worry-Free Guarantee, so you can rest easy knowing we’ve got your back. Just relax and enjoy the show!

Oldies Music serving the Madison, WI area

These Oldies Music serve the wider Madison and Dane county area and travel to Monona, Fitchburg, Middleton, McFarland, Springfield, Waunakee, Verona, Cottage Grove, Oregon, Sun Prairie, De Forest, DeForest, Windsor, Cross Plains, Dane, Stoughton, Morrisonville, Stone, Brooklyn, Belleville, Deerfield, Mount Horeb, Lodi, Black Earth, Marshall, Arlington, London, Cambridge, Mazomanie, and Sauk City.