How 'South Side' turned the Black Midwest experience into one of the best shows on TV

Explaining HBO Max's hit series South Side is like trying to explain religion to a nonbeliever. You spend a lot of time trying to put into words what can only be understood through experience. The jokes are so precise and hit so hard that you'll yell-laugh and run around the room until you're out of breath. The best you can do is earnestly press your HBO Max login into the palms of the uninitiated like a missionary leaflet. Won't you give South Side a watch today, beloved?

The show follows Simon (Sultan Salahuddin) and Kareme (Kareme Young), two repo men working for a rental furniture company, on their adventures across the city of Chicago. Season 2 of the series was released on HBO Max in November 2021 and the show continues to garner a devoted audience, as evidenced by the passionate outcries on social media for HBO to greenlight a third season. While it is set in the Windy City, what is striking about the show is the way that it also speaks to a regional vibe – it is truly a middle American comedy, even though the characters aren't who would initially come to mind when you think of that phrase. Black folks in the midwest are preternaturally mellow, but also have a sense of cool and family-centeredness that is evocative of the Deep South. And as a Southerner who lived in Detroit for two years and with family scattered across the middle of the US, it was hard to miss the Black Midwestern flavor that makes South Side irresistible to watch.

The creators, Bashir Salahuddin and Diallo Riddle, wanted to make a show about one of their hometowns and settled on Chicago, from which Salahuddin hails. They have been fixtures in Hollywood for well over a decade, and are known for creating such fare as IFC's Emmy Award-winning mock variety show Sherman's Showcase and their writing on TBS' Tracy Morgan comedy The Last O.G. "I think the idea simply was, let's make a really robust comedy, but let's use the actual types of things that you would see coming from the South Side of Chicago," Salahuddin told Mic during a recent video chat with the pair. "Because it's a much more diverse place than we ever really get credit for, especially when you look at the news." Chicago's South Side is often used as a boogeyman in the public imagination as full of violence and despair, but this show gives us another view of it as a place full of vibrance.

Season 1, which aired on Comedy Central, laid the groundwork for the show's current success: nuanced jokes that land as powerfully for Chicago natives as they do for outsiders. According to Salahuddin, that's something that Black comedy warrants. "We deserve stuff that is as good as the stories we tell each other," he says. Building a rich, honest portrait of the South Side clearly resonated, as the show grew in popularity even as it moved to HBO Max for its second season.

Because of the organic growth of South Side's fanbase through word of mouth, Riddle went into Season 2 hoping not to disappoint early adopters of the show. "I think that's where that evangelical sense [among viewers] comes from. It's a really high-quality show that doesn't have a whole bunch of stars in it, doesn't have a whole bunch of people breathing down your throat trying to force it on you. No, you discover it, and realize 'this show is great!'"

Both Salahuddin and Riddle come from large families, and that's where they developed their comedic instincts. "You figure out what are the things that I can say that are going to make this whole table laugh," Salahuddin says. Now, he and Riddle tap into the talents of their networks to make South Side a success. Many of the main cast members are relatives or longtime friends: Bashir's brother Sultan Salahuddin plays the always-scheming main character, Simon, and his sister Zuri Salahuddin is pitch-perfect as the perennially unbothered Stacy, both of whom are employed at the fictional Rent-T-Own. Twin brothers Kareme and Quincy Young, childhood friends of Salahuddin, play their namesakes on the show. Chandra Russell, who acts as Officer Turner opposite Bashir on the show, is his real-life spouse. Riddle rounds out the outfit as the upwardly striving lawyer Allen Gayle.

"We were really fortunate in South Side that we put a lot of family and friends on the show and in the writer's room," Bashir says. Bringing their folks with them has meant they are able to have honest portrayals rooted in their own experiences.

The show excels at highlighting the complexities of family life. We experience Simon as a doting yet financially stretched father to his many children. The bickering between twin brothers Kareme and Quincy is only exacerbated by the power dynamics that exist between them: Quincy is Kareme's manager at Rent-T-Own, but Kareme owns the family house they share. Simon's Uncle Spike is the quintessential smarmy catdaddy who is always into wild shit, whether it's acting as an unlicensed street medic for Simon and Kareme's illegal ambulance operation, or beckoning Simon to increase the billow on his suit as he prepares for a Chicago stepping contest. "Nope, mmm-mm. It's not flowy enough," Uncle Spike chides Simon. "See, when you step, you gotta look like you're wrestling a queen-sized bedsheet." While hyperbolic, these characters feel like home to anyone who has grown up or lived in the Midwest, yet still relatable to those who haven't.

South Side leans into Chicago culture and midwestern culture – hard. It's what is most enjoyable for fans like Tonja Renée Stidhum, a scriptwriter for Tonal and writer/producer also from the South Side of Chicago. She was first introduced to the show through her work as an entertainment writer for The Root. The Chicago-specific references — the Juke-A-Thon contest, Harold's chicken, the images of the South Side's bungalow homes — are more than what you would see on a weekend visit to the city or from a few hours on Youtube. Tonja appreciated encountering characters that reminded her of the everyday folks she grew up with. "I just love that it was about these regular people. There's a lot of Black shows, and no shade to them because it's great that we have that representation, but, a lot of shows are about the ‘Brunch Blacks,’ like I call them — the highly elite, upper-middle-class Black people." To Stidhum, there is value in showing more than the glossy lives of upwardly mobile Black folks. "These people who work regular jobs, regular people, are worthy of stories as well." Sitcoms like Roseanne, That 70's show, and The Drew Carey Show come to mind when you think of shows rooted in Midwestern culture, but not since "Martin" has there been a comedy that so powerfully located the Black Midwestern aesthetic.

A working-class show based on one of the most ubiquitous types of stores in Black neighborhoods is something that often piques people's interest. Riddle says, "I get asked, well where did y'all come up with Rent-T-Own?" The answer: Quincy, who plays the manager of the store, worked for Rent-A-Center in real life. It presented Salahuddin and Riddle with the flexibility to take the show in any direction they wanted. "It is a terrible, predatory business, but it's also a business that forces its employees to get out into the city, and for us, that was the thing about it that was valuable," says Bashir. This structure is the big bang that allows Simon and Kareme to expand into the nooks and crannies of Chicago's neighborhoods and explore the multiple galaxies that exist in them. "For us, our goal was always a show that could do anything."

When people use the word "hustle" to describe a city, usually New York comes to mind, but the cold weather metropolises of the midwest are defined by their own brands of hustle. The need to make something shake is baked into Black life in those places, which are often facing the consequences of economic disinvestment and racial segregation. To Jaelin McGull, a professional photographer from St. Louis, Missouri, South Side is "...one of the funniest shows on streaming networks right now." He identifies most with the main character Simon, whose entrepreneurial spirit can be found in many Black communities. "I feel like Simon wants to just live a simple life and not be bothered. But also, he works but finesses his work in this cool way, so it's always pretty funny," McGull says. In his own work covering Black musicians and Black life, "I definitely think there's a hustle to my work."

Aside from the storytelling and the fresh-faced cast of characters, South Side is also innovative in how it collaborates with musicians on the show. Without a big budget, they've had to make up for it by discovering and working with up-and-coming artists. To do that, Riddle says, they rely heavily on the expertise of their music supervisor and friend, Anthony Demby. Both Riddle and Salahuddin praised Demby's ability to surface new artists to feature and a knack for matching the music with the moment. "We always knew we wanted our show to sound not like anything else on TV. And Demby has the range to go with us no matter what kind of music we're talking about,” Riddle says. “And in the end, he also knows, like Bashir said, that we don't have the pocketbook that these other shows have." South Side drill rapper Sasha Go Hard performs the brazenly catchy theme song, and you can find a who's-who of Chicago talent throughout Seasons 1 and 2. As a result, the sound of the show is fresh, but still rooted in the identity of the city.

South Side is scrappy, but it still attracts celebrities who see the vision and want to participate as guest stars. Rappers Vic Mensa, Chance the Rapper, and Dreezy make appearances, as well as actress LisaRaye McCoy, radio legend Ed Lover, and comedians Lil Rel Howry, Deon Cole, Sommore, and Kel Mitchell. Salahuddin attributes that to the fact that South Side gives them a chance to make straight-up comedy, even if it doesn't have all the bells and whistles they are used to at larger Hollywood productions. "We're so grateful that music people can come to us and be funny,” he said. “I think that's something we want to keep going."

In a world where it feels like everything is constantly fracturing and shifting, South Side offers up the comfort of soul-cleansing laughter. By leaning into Black Middle American values, its creators have given the world something to smile about.