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Edgewater resident Jason E. Jackson, center, reacts as he crowned winner of the “Chicago Sings Karaoke” competition following a six contestant finale performance at Park West theater on Sunday.

Edgewater resident Jason E. Jackson, center, reacts as he crowned winner of the “Chicago Sings Karaoke” competition following a six-contestant finale performance at Park West theater on Sunday.

Lou Foglia for WBEZ

Chicago crowns its first karaoke champion

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 herself sang “Dancing in the Street” by Martha & 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, before assuring the competition will be back next year.

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



Edgewater resident Jason E. Jackson performs during the “Chicago Sings Karaoke” competition finale at Park West theater in Chicago on Sunday.

Edgewater resident Jason E. Jackson performs during the “Chicago Sings Karaoke” competition finale at Park West theater in Chicago on Sunday.

Lou Foglia for WBEZ

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

“I think the pandemic hit everybody really hard. I’ve gone through a tough time these past few years,” he said. “This money is going to mean a chance for me to rebuild.”

Sunday’s showcase featured six finalists, who each sang two songs, and included everything from Sam Cooke to Celine Dion to Michael Jackson. The competition was the culmination of the month-long 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 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.



Edgewater resident Jason E. Jackson performs during the “Chicago Sings Karaoke” competition finale at Park West theater in Chicago on Sunday.

Edgewater resident Jason E. Jackson performs during the “Chicago Sings Karaoke” competition finale at Park West theater in Chicago on Sunday.

Lou Foglia for WBEZ

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

When she won at that location, 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 to 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.



Jason E. Jackson performs after being crowned the city's first-ever karaoke champion, with his fellow finalists in the citywide competition behind him.

Jason E. Jackson performs after being crowned the city’s first-ever karaoke champion, with his fellow finalists in the citywide competition behind him.

Lou Foglia for WBEZ

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 you’d typically find 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.

WBEZ’s Lauren Frost contributed.Courtney Kueppers is a digital producer/reporter at WBEZ. Follow her @cmkueppers.

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