On December 6, part of the cast, directors, and show supporters gathered at the DuSable Museum to watch an advanced screening of HBO Max’s critically acclaimed South Side season three. South Side is not only an ode to Chicago, but a ride of comedic relief that embraces the cultural complexities of the city.

The series primarily follows the misadventures of Simon and K, portrayed by cocreator Sultan Salahuddin and fresh face Kareme Young, as they repossess furniture from indebted families for the show’s Rent-to-Own (RTO) store.  

Based on the premeire, which explored the abyss of Lower Wacker Drive and Officer Goodnight’s incompetence to properly diffuse any situation, it’s clear season three will be no different in its hilarious depiction of everyday life and people on Chicago’s South Side. According to the creators, this was nothing short of intentional. 

“We want you to know what you’re getting into” in the first episode, affirmed Bashir Salahuddin, cocreator, EP, and actor on the comedic series. 

WBEZ Reset host Sasha-Ann Simons moderated an enriching conversation after the screening where they shared much about the inspiration and development of the show. “When you’re an episodic series, you’re really like someone’s meal. You really have to feed them.” An episodic series means that each episode does not build on the previous one, so character development is only gradual, and directors have to make sure each episode can stand on its own. 

The first episode of the season spotlights some of the main characters’ flaws and their inability to acknowledge them. Simon can’t accept that the nature of his job, and how strong he is at it, essentially makes him appear “heartless” to the victims of repossession. Officer Goodnight overreacts to petty crimes, often leading him to underperform his duties as a cop. Then there’s characters like Officer Turner, Q, and even Stacy serving as the liaisons between rationality and nonsense. 

During this season, the series will explore the social, political, and living conditions that led characters to become who they are today. Showrunner, EP, and “Alderman Gayle of the 51st Ward” (some fictional area comparable to Englewood), Diallo Riddle, said how fulfilling it was to get to know each character better. “Because these characters are intentionally complex, we feel comedy is more fun when dealing with three-dimensional characters” Riddle said, “while exploring unexpected storylines and plot twists.”

In one scene, officers Goodnight and Turner end up at the car pound in an attempt to recover a stolen police SUV—and prove that not even their badge can get them past the wait times and red tape that city pounds are notorious for. At some point in the episode, the cast hilariously grapples with a bed bug infestation at the repo store.

According to the creators, the true brilliance of the show comes from a collective of minds and experiences. “The show South Side is what it is specifically because of the constant influence of Black women,” said Riddle. “I sat back one day and realized there were more Black Women in the writer’s room than Black men. And that’s not a typical thing, at least not in Hollywood.” 

Riddle went on to describe how actresses on the show, Chandra Russell (Officer Turner) and Zuri Salahuddin (Stacy), constantly come up with scenes and lines that wouldn’t occur to them otherwise because of distinct life experiences. “Their voices are more mature, and that’s why you constantly see stories on this show that you don’t see anywhere else.”

For many of the characters we see, it’s their first time on the big screen. Take the snow cone guy from the premiere. One day, Bashir Salahuddin, who plays Officer Goodnight, craved an ice cone in real life while filming the season. He asked his mom, who sat in the audience during the screening, where he could go to find the Chicago summer gemstone and was pointed in the direction somewhere south of 83rd and Vincennes. Next thing he knew, the guy who sells them is making him laugh endlessly without having any idea who his customer is. Now, he’s in the show and making America laugh, too. 

When the creators were asked if the comedy could be deemed a classic, Sultan Salahuddin (Simon) confidently asserted, yes. “I think it’s a very special and anointed show for many reasons you cannot see and can see on screen. I think it’s in the DNA of the show.” He further explains how they survived a network switch when the series, originally aired on Comedy Central, was bought by HBO Max during the pandemic. “A lot of shows don’t survive that jump,” he exclaims. “We’ve survived the eye of a needle several times. So I think the proof is in the pudding.” 

The directors and actors reminded other creative folks that—before they seek recognition or to work with big names—often the most talented and supportive people are within arms reach. “When you talk to people about who’s the funniest person in your life, some of you are sitting next to them. Some of them are people you went to school with. Ya cousins, ya aunties. We really are tryna have the city be redefined. More comedically, more joyously, more of the city we know. We thought who better to do that than actual Chicagoans,” said Bashir.

This season’s viewers can expect their favorite characters to explore parts of themselves previously unseen, while an uptick in outlandish circumstances results in the chaotic world that makes South Side so tantalizing to fans. 

According to the writers, in this season, Alderman Gayle is “looking for ways to keep the things about being an alderman that he likes but lose the work.” We’ll get a peek into the “connections Simon has, explored passions, and his ability to embrace Kwanza.” And as expected, Goodnight, in simplest terms, will “get worse over time.” 

Add a Lollapalooza episode (yes, Lolla) and even some animated scenes, and South Side is confidently creating new boundaries for what it means to be an original, modern-day comedy series. You can be from anywhere around the country and identify with some character or experience portrayed in the show. Don’t just take our word for it. 

“It doesn’t matter if you’re from southwest Atlanta, south Philly, the south Bronx, [or] South Central,” attested Riddle, “If you are from the South Side, you’ll take away a little bit of what makes the show work.”

The instant classic is now streaming on HBO Max, with two new episodes airing on Thursdays.

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Kristian is a writer and visual storyteller, inspired by sharing narratives that positively shift and shape perspectives. She last wrote about vegan comfort food in Hyde Park in Best of the South Side 2022.

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