Discover 126 professional crooners available for hire in Milwaukee, Wisconsin, United States, backed by 266 reviews from real clients averaging 5 out of 5 stars. These smooth jazz vocalists bring sophisticated entertainment to weddings, corporate events, and private celebrations with prices from around $150 and an average of $500.
Of the 126 suppliers listed here, one is based within 30 miles of Milwaukee. The other 125 are willing to travel there.
Based more than 30 miles from Milwaukee, nearest first
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Book from $1500 (USD)
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Book from $500 (CAD)
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Wedding Singers in MilwaukeeHiring a crooner singer in Milwaukee typically costs between $150 and $1,450+, with most bookings averaging $500 for professional performances. Pricing reflects performance duration, accompaniment and the performer's experience. Solo crooner performances with piano or backing tracks offer excellent value for intimate events, while full band arrangements are available for clients seeking premium entertainment experiences. Most performers include repertoire consultation and event coordination in their standard fee. Contact the supplier you like for an accurate quote.
Based on 188 enquiries for Crooners at events in the United States, made through this site in the last two years. Updated 17 October 2026.
Jerry Armstrong Tribute Artist
"Jerry did an amazing job! He was on time and brought all of his equipment, he knew all the songs and sang them very well. He interacted with the crowd, he was very friendly and funny. I would definitely hire him again. -Rachel W, Tinley Park, IL"
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."
Gerald Harris Singer Guitarist
"Blessed addition to our mothers interment
Gerald was a breeze to work with and was very accomodating of our song choices. He arrived hour before the ceremony to set up. The whole affair went off perfectly. Thank you, Gerald
Rating:
Reviewer: Brian Konkler
Event date: March 19th, 2021
Services provided: Gospel Singer"
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"
The Rick Levine Band
"Fantastic Band! Rick is easy to work, dance floor was full all night long. Guests are still talking about how the Rick Levine Band helped make my event a success! Thanks."
James Anthony's Salute to Sinatra
"James Anthony was amazing when he performed for the United States Congress on Capitol Hill in Washington, D.C. He arrived early to rehearse with a 20 piece group of musicians and was a huge hit. The Congress Members and Senators were asking where I found him and we at the Las Vegas Metro Chamber of Commerce absolutely recommend him. Due to popular demand, we brought him back the next year to perform for the US Senate for their annual gala."