Aria crown: Chicago has a karaoke champion

In the first citywide singing contest, Chicago Sings Karaoke, Jason E. Jackson beat out 540 others to take the top prize of $5,000. Mayor Lori Lightfoot belts out ‘Dancing in the Street.’

SHARE Aria crown: Chicago has a karaoke champion

Jason E. Jackson (center) won Chicago’s first citywide karaoke contest Sunday night at Park West. His formula: Sing opera.

Lou Foglia/For WBEZ

As confetti fell at the sold-out Park West theater, Jason E. Jackson was crowned Chicago’s karaoke champion Sunday night in the first-ever citywide competition.

“I’m floored, and I am so honored,” said Jackson, who donned a shiny gold bow tie with a black shirt and a pinstriped vest and pants.

Jackson’s renditions of “I Believe in a Thing Called Love” by The Darkness and a show-stopping performance of the opera aria “Nessun Dorma” that brought the crowd to its feet earned him bragging rights and a $5,000 prize presented by Mayor Lori Lightfoot — who sang “Dancing in the Street” by Martha and the Vandellas as the judges deliberated. 

“It’s been a gift to be in the presence of these incredible artists and performers,” Lightfoot told the crowd.

Jackson, 45, who lives in Edgewater, said he opted for an opera number as a way to stand out from the competition. It was immediately clear his gamble paid off. One judge told Jackson that he “touched everyone here,” and another called the performance “truly mesmerizing.” 

As for Jackson’s plan for the winnings, he had three words: “Bills, bills, bills.

“This money is going to mean a chance for me to rebuild,” he said.


Edgewater resident Jason Jackson wore a gold bow tie and sang numbers by Puccini and The Darkness in the Chicago Sings Karaoke finale at Park West.

Lou Foglia/For WBEZ

Sunday’s showcase featured six finalists, who each sang two songs, and included numbers from Sam Cooke, Celine Dion and Michael Jackson. The competition was the culmination of the monthlong contest. In the first two rounds, judges evaluated 540 Chicagoans who sang at 18 venues in neighborhoods across the city.

The grand finale — which concluded with Jason Jackson leading a group performance of Journey’s “Don’t Stop Believin’ ” — attracted hundreds of enthusiastic karaoke fans who sang and danced to every song. Near the stage, a panel of five judges evaluated the contestants and offered feedback on song selection, performance, vocal range and even how well they engaged the audience. 

For Erendira Izguerra, the path to the Park West started at Mi Tierra in Little Village, where she said she was hesitant to get up and sing, but her friends “basically forced” her to sign up.

When she won there, she advanced to the semifinals, where she wowed the judges at Simone’s bar in Pilsen by belting out “La Cigarra” by Linda Ronstadt and “Échame a mí la Culpa” by Amalia Mendoza.

Despite being around mariachi music since she was a teenager, the 29-year-old said she doesn’t really consider herself a singer. 

“Honestly the fact that I made it to the finals gives me hope to actually try singing more often,” she said.

Izguerra’s fellow finalist Brandon Dodson — a 35-year-old Rogers Park resident who has been singing since he was a kid — also secured his spot at the Park West thanks to his semifinals performance at Simone’s. That night, Dodson took the mic and asked the crowd, “Anyone like some old-school R&B?” before diving into Brian McKnight’s 2001 ballad “Love of My Life.”

And Jaleel Amir’s journey to the finals began at Randy’s Lounge in Grand Crossing — with his mom there to cheer him on. Meanwhile, Rashada Dawan and Lauren “Elle Michelle” Gaines both got to Park West by singing Aretha Franklin.

By the time the semifinals rolled around, the competition was fierce, and the voices were all refined — making the contest feel more like “American Idol” and less like the kind of karaoke typically found in bars.

But in round one, that eclectic magic of karaoke was alive and well, with unknown talents captivating a crowd with soulful renditions of Nina Simone’s “Feeling Good” or Chris Stapleton’s “Tennessee Whiskey” — followed, of course, by off-key Elvis serenades. But for a few minutes, each of the hundreds of participants got to be the star — and feel like a champion.

Courtney Kueppers is a digital producer/reporter at WBEZ. Follow her @cmkueppers.

WBEZ’s Lauren Frost contributed.


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