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Hip-hop artist Che “Rhymefest” Smith shares his favorite Chicago memories

The hip-hop artist and aspiring politico remembers Regal talent shows and artists’ communities.


With multiple mix-tapes and two well-received albums under his belt, including last year’s El Che, hip-hop artist Rhymefest (above, right), 33, made his first foray into politics with a run for 20th Ward alderman in February’s election. He made it to the runoff but conceded earlier this month and is now back in the studio, working on a new album. The South Shore High School grad looks back on some of his biggest early influences, including a Wicker Park artists’ loft and the Regal Theater talent shows where he cut his teeth as a rapper.

On missing the Point
“I used to go to a place called the Point [at Lake Shore Drive]…where they would have artists programs for young up-and-coming rappers, and they let the young people come in and break-dance and do our music.”

On lofty ideals
“The first cultural institution I attended was created by a guy named Billy [‘Upski’] Wimsatt. He had an artist village called Vision Village [loft in Wicker Park in the mid-’90s], and it was set up so young people from around the city could attend and express ourselves. It doesn’t exist anymore but it…had a major impact on my life, as well as a small literary club called Literary Explosion that was on Damen.”

On staging his talents
“When I was coming up, they used to have monthly talent shows at the Regal Theater [on 79th Street near Stony Island Avenue], which I don’t believe they do anymore, but that was the first time as an artist I was able to really express myself to a large group of people.”

On a musical Wonder
“I used to work for a company called Andy Frain [Services], and one of the first performances I ever saw was a concert, Stevie Wonder, at 12 years old as an usher. It was amazing.”

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