Cabaret Queen Denise Tomasello

Embracing the Great American Songbook while fellow high schoolers were dancing to ’70s rock, Denise Tomasello has emerged as Chicago’s quintessential chanteuse.

Known as “Chicago’s Queen of Cabaret,” Denise Tomasello has been entertaining audiences in many of the area’s finest venues for decades. After a nearly three-year hiatus from show business, this acclaimed chanteuse is once again taking to the stage with her stirring interpretations of the Great American Songbook.

Tomasello is a native of Melrose Park, where she attended Proviso East High School. Her mother worked at Amling’s Flowerland, and her father was a delivery driver for the old Burny Brothers Bakery.

“As a child, I remember we would go to church at Our Lady of Mt. Carmel and have these wonderful family dinners with my grandparents and other relatives,” Tomasello says from her home in north suburban Chicago. “Sunday was always my favorite day.”

Tomasello has had a lifetime love affair with the music of composers like Irving Berlin, George Gershwin, Cole Porter, Sammy Kahn and other authors of the Great American Songbook. The same can be said for the generation of singers she admired while growing up.

“When I was younger, I remember my parents and I always used to watch The Judy Garland Show on television,” Tomasello recalls. “I never really liked the newer songs, the rock or pop. I was never really into them, even when I was a teenager.”

Instead, Tomasello, along with her parents, listened to artists like Streisand, Sinatra, Martin and Bennett. Her uncle Joe Toullo played the saxophone and toured with the Lawrence Welk Orchestra, but it was Tomasello’s sister Diane who nudged her toward her chosen career.

“My sister’s boyfriend was starting a show band, and they were looking for a female singer, so she forced me to go to the audition,” Tomasello says. “I never really sang in school, but I did play guitar and sing around the house with my sister Debra. I was 19 at the time, and I was thrilled when I got the job.”

The band played hits from the ’70s throughout the Chicago area. Tomasello went on to form a trio of her own so she could showcase the repertoire that was near and dear to her heart. Local agent and music manager Tony Leanardi booked her into the Tack Room at the Arlington Park Hilton, where local bands held sway. Meanwhile, national headliners like Eydie Gormé, Steve Lawrence, Kenny Rogers, Peggy Lee, Frank Sinatra Jr. and Nancy Wilson were performing upstairs in the Hilton’s prestigious showroom. The venue’s entertainment director heard Tomasello singing in the Tack Room and approached her.

“He came up to me and said, ‘What are you doing here? You should be downtown. I know this jewel of a room that is perfect for you.’ He told me he was bringing an agent in the following night, but he never showed up,” Tomasello says. “Oh well, that’s showbiz. But on Monday morning, the phone rang, and I was told an audition had been scheduled for me at Sage’s. I hadn’t planned on being a cabaret singer. In fact, I had never been to a cabaret show in my life. I had to go on cold and sing three songs. The entertainment director shook my hand and hired me for two weeks. That two weeks ended up being a six-year engagement.”

With a style reminiscent of Minelli and Garland, Tomasello took the local cabaret scene by storm. Settling in at Sage’s, she began refining her craft. In this intimate setting, she was able to not only make each song her own, but create a special bond with her audiences. Critics like Rick Kogan and Larry Kart wrote rave reviews, and the who’s who began to turn out in force.

“Sage’s was across the street from the Ambassador East’s Pump Room, so all the celebrities used to come in,” Tomasello says. “On any night, you could see Irv Kupcinet or Harry Caray. That was where I became a chanteuse. I loved it so much I sang there year ’round. I didn’t even want to take a vacation.”

That was a different era. From the 1950s through the 1990s, Rush Street had a vibrant entertainment scene, boasting clubs like Blondies, Billy’s, Yvette’s, The Acorn, Toulouse, P.S. Chicago and the biggest of them all, Mister Kelly’s. With her repertoire of classic torch songs like “Just in Time,” “Our Love is Here to Stay” and “Come Rain or Come Shine,” Tomasello fit right in and played them all.

Word of her talent spread beyond the Chicago area, and Tomasello was soon booking engagements at the Hollywood Roosevelt Hotel, Cinegrill and Four Seasons Hotel in Los Angeles, as well as the 88’s and Townhall in Manhattan. She also got the chance to open locally for Don Rickles and Alan King. After she opened for Jackie Mason at the Tropicana in Atlantic City, the legendary comic called her, “an amazing singer and brilliant comedian. She is so natural on stage, like a female Dean Martin.”

Along the way, she developed a close personal relationship with Frank Sinatra Jr., which led to her working with some of the top names in the business.

At the time, Chicago was the capital of the advertising industry, and countless major commercials were being produced there. Tomasello’s voice reached a national audience on the soundtracks of ads by Toyota, American Airlines, Motorola and Oscar Mayer.

As the years went by, the entertainment scene changed dramatically. Rooms like Sage’s were closing, and deejays began replacing professional musicians. Tomasello’s career continued to thrive thanks in part to Ron Onesti, who started booking her at his Italian fests, where she headlined for years.

“I have to give so much credit to Ron,” Tomasello says. “He gave a great boost to my career. He is so wonderful to work for, and he treats his performers with such respect and courtesy.”

Things took a tragic turn when Tomasello’s mother passed away in 2017, followed by the death of her beloved husband, Don Conover, in 2020. Then, the pandemic struck, hitting the entertainment industry particularly hard. Tomasello ended up putting her career on pause for three years.

It was only a matter of time before Tomasello’s love for music and life reasserted itself. She made a triumphant return to the stage on June 12, 2022, when she performed “Judy, Liza, Barbra and Me” with her 17-piece orchestra at Onesti’s Des Plaines Theater. Then, it was back to her cabaret roots on Oct. 15, 2022, when she wowed audiences at Davenport’s Cabaret and Piano Bar in Chicago.

She also played a key role in Davenport’s Chicago Emerging Artist Showcase in August, during which five young musicians competed for the first-ever Denise Tomasello Scholarship. The grant was established by Tomasello to foster the careers of young cabaret singers on the local entertainment scene. She will soon be launching the Don Conover Foundation in loving memory of her late husband.

“Music has the power to heal. I really do believe that” Tomasello says. “It’s given me so much, and I’m happy to do my small part to give back.”

The above appears in the January 2023 issue of the print version of Fra Noi. Our gorgeous, monthly magazine contains a veritable feast of news and views, profiles and features, entertainment and culture. To subscribe, click here.