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‘South Side’ ups the Chicago ante for a bold season three

On the set of HBO Max’s “South Side,” somehow nearly every cast and crew member is connected to another — either through their family tree, a decades-long friendship or a shared love for showing the joy in an often misunderstood part of Chicago. Sometimes it’s all three.

After moving to the streaming platform from Comedy Central for season two, “South Side” caught the eyes of a wider audience. This means the pressure is on to make season three of the Englewood-based show even funnier.

The new season of the comedy about the harebrained schemes of hustling Rent-T-Own workers Simon James (Sultan Salahuddin) and Kareme “K” Odom (Kareme Young) premieres on HBO Max on Dec. 8th.

Since its premiere in 2019, the show has garnered acclaim for its true-to-life portrayal of the South Side, an area where Chicago-based shows often fall short. Having a writing staff predominantly from the South Side can’t hurt.

“We’re really pushing the boundaries in the writer’s room this season,” says co-creator Bashir Salahuddin. “Fans ain’t seen nothing yet.”

Like many of the cast, Salahuddin wears quite a few hats on the “South Side” set. He executive produces, writes, directs and stars as the uptight officer Goodnight.

Karame (Kareme Young, left) and Simon (Sultan Salahuddin) embark on new moneymaking schemes in the new season of “South Side.”

He and brother Sultan Salahuddin — a co-creator, star and writer — grew up on the South Side and make showing joy and Black culture a major priority.

Bashir Salahuddin cites Chicago itself as a central character in the story this season.

Some settings this season include Lollapalooza, the Central Auto Pound on Lower Wacker and the South Shore Cultural Center, where a Kwanzaa special takes place. One episode sees Goodnight’s partner, Officer Turner (played by Bashir Salahuddin’s real-life wife and show writer Chandra Russell), head to her family’s home in the south suburbs, and another film at Jeff’s Red Hots on Cicero Avenue.

“South Side” scripts can sometimes act as inside jokes to Chicago natives. But those who aren’t completely in on the joke still are able to enjoy themselves.

From the idiosyncrasies of Chicago politics to Black funeral culture, the sitcom has found a specificity that has managed to appeal to a mass audience.

“One of my favorite compliments I get is when people who aren’t from Chicago watch the show, love it and say, ‘This is my favorite show.’ And then people who are from Chicago, they have a little bit of extra,” Bashir Salahuddin says.

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Officer Turner (Chandra Russell, right) will visit her family home in the south suburbs during season three.

Beloved and prominent Chicagoans will continue appearing on the show this season. Chance the Rapper will reappear as villainous Herb, and some other classic Chicago names will pop up, too. Among them are local TV personalities Leon Rogers and Val Warner, actor Lahmard Tate and rapper Vic Mensa.

The writers room, predominantly African American and female, tries not to “fly anyone in,” when it comes to actors, says “South Side” co-creator, writer and actor Diallo Riddle. Instead, Riddle says, they often pick from the smorgasbord of local talent.

“It’s a variety of people who are both sorts of household [names] and also people who people just love to death,” says Bashir Salahuddin.

Bashir Salahuddin and Riddle, both science fiction fanatics, hint at a season that takes inspiration from “Star Wars” and Christopher Nolan movies.

But even though they may dip into the surrealist pond, “South Side” plotlines are grounded in truth, and the writers’ need to keep their “ears to the streets,” Riddle and Salahuddin say.

Riddle’s Allen Gayle will return this season, this time as a newly-elected alderman, which is surely a storyline rife with Chicago insider humor.

“The goal is to do things we have not done yet,” Bashir Salahuddin says. “That does sometimes push us away from things that people are expecting. I do think that even though we do things that are wacky, and silly and funny, I wouldn’t call our show 100% grounded, but I wouldn’t call it ungrounded either, because sometimes truth is stranger than fiction.”

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Diallo Riddle, co-creator of “South Side,” returns in season three as Ald. Allen Gayle.

Season three will have a shorter order of eight episodes.

“What was kind of unintentionally cool about eight episodes is that it meant that we got to tell eight extremely packed, dense with jokes and meaning and revelations episodes,” Riddle says.

On one of the final days of filming, Sultan Salahuddin’s Simon has sequestered himself in a cave, hiding from the world after an unknown event in the season finale sends him spiraling. His new home is complete with wall drawings mapping out his new neighborhood.

Among James’ essentials down in the cave include two marijuana dispensaries, a Jewel-Osco, an Aldi and a trade school.

The reasoning behind a seemingly prehistoric cave based in Chicago is not revealed to visiting reporters, but the “South Side” magic grounds the storyline.

“Behold, Simon’s megalopolis,” Sultan Salahuddin’s Simon cackles during a scene, as he shows off his cave drawings.

Ahead of the season’s premiere, the show’s co-creators hope they’ll have the chance to return to the joyful “South Side” world for a fourth season.

“This show never lost a viewer,” Riddle says. “I think that if you watch one, you’ll watch them all. And that means a lot to us. So we just want people to see the show, and get it in front of as many people as possible.”

Mariah Rush is a staff reporter at the Chicago Sun-Times via Report for America, a not-for-profit journalism program that aims to bolster the paper’s coverage of communities on the South and West sides.

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