Bringing the timeless charm, rich tone, and magnetic stage presence of Sinatra, Dean Martin, Elvis, and Johnny Cash to your once-in-a-lifetime celebration.
When you hire Winston, you aren’t just booking background music—you are introducing a distinctive atmosphere of classic lounge luxury that captivates every generation in the room.
With a lifetime of rigorous vocal training and a decorated theatrical background, Winston brings Broadway-caliber vocal precision and effortless charisma to every event. His stage accomplishments include winning two prestigious Jerry Awards for standout leading roles in The Drowsy Chaperone and Footloose.
Whether performing intimate jazz ballads during your ceremony or swinging Rat Pack anthems as guests sip champagne, Winston creates an unforgettable soundtrack tailored exclusively to your vision.
From the golden age of Las Vegas to dusty Sun Studio country and Broadway showstoppers. Explore Winston’s signature catalog below.
Watch Winston deliver smooth Sinatra and Dean Martin classics at a premier Milwaukee historic ballroom.
Emotional acoustic & orchestral renditions of Elvis Presley's "Can't Help Falling in Love" and Johnny Cash.
Transparent, all-inclusive entertainment options crafted specifically for wedding ceremonies, cocktail hours, and luxury dinner receptions.
Intimate, breathtaking acoustic vocals that elevate your walk down the aisle.
The signature Rat Pack supper club experience while your guests mingle and celebrate.
Sophisticated dinner music culminating into an unforgettable live First Dance.
Combine Ceremony + Cocktail Hour + Dinner Reception into a seamless, unified soundtrack for your special day.
Proudly performing at premier historic venues, private lake clubs, and luxury ballrooms throughout Wisconsin.
"Winston blew our wedding guests away at our Pfister reception! His voice has that rich Sinatra depth you simply don’t hear anymore. Our grandparents and college friends were all raving."
"Having Winston sing during our cocktail hour set such a classy, high-energy tone. He arrived early, was impeccably dressed in his tuxedo, and his Jerry Award talent is evident from the first note."
"His live rendition of 'Can’t Help Falling in Love' for our first dance had half the room crying happy tears. The absolute highlight of our wedding entertainment!"
Dates book quickly for the Wisconsin wedding season. Fill out the details below to receive a personalized quote and confirmation within 24 hours.