Diallo Riddle as Allen Gayle in South Side.
Photo: Courtesy of Comedy Central

The South Side of Chicago is bustling with hustlers.

Ask me how I know. Well, I’ll tell you anyway. As a South Side Chicago native, I was not only around hustlers, I was raised by them. Whether it’s the beloved candy lady who sold those delightful Frooties and Chews out of her bungalow basement or the ubiquitous man selling fresh towels at the 95th/Dan Ryan train stop, making money isn’t just a routine, it’s a lifestyle.

That very lifestyle has been immortalized in Comedy Central’s new show, South Side.

From the official Comedy Central synopsis:

South Side is an aspirational, scripted comedy set in and around the working class neighborhood of Englewood on the South Side of Chicago. The show follows two friends who just graduated community college ... so now they’re ready to take over the world! But until they do they’re stuck at Rent-T-Own, a retail-rental crossroads where the South Side’s vast ensemble of characters come together. Despite the obstacles of inner-city life, these friends and their co-workers all strive to achieve their entrepreneurial dreams. Brought to life by local Chicagoans, both in front of and behind the camera, this show gives viewers an authentic portrayal of what life on the South Side is all about. It’s evidence that what you see on the news is only a small piece of the city. It’s written by Bashir Salahuddin (Glow) and Diallo Riddle (Marlon). Salahuddin, Riddle, and Michael Blieden – all Late Night with Jimmy Fallon alumni – are executive producers.

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I had the pleasure of attending the wrap party for South Side in West Hollywood, where we watched the first two episodes, “XBOX” and “Sell Yourself” while juking to house music and sopping up mild sauce with chicken wings. Along with chatting with Salahuddin and Riddle at the party (who were equally geeked about their upcoming project), Riddle got on the phone with me last week to thoroughly discuss how the show came to be, why this particular facet of Chicago is important to showcase and, of course, the blackest moment on set.

While Salahuddin is from Chicago, Riddle is actually from Atlanta. However, his roots were cosmic in birthing this show.

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“Bashir and I wanted to tell a story about the towns that we were from and originally we had worked on two pilots at HBO for two years apiece—a total of four years—based on my hometown of Atlanta,” Diallo told me. “But then we hit that thing that sometimes happens, unfortunately, in this business where another show about my city came up and we truly do think that it impacted our ability to get that show all the way to series.

“In fact, we’d already been ordered to series [i.e. the network ordered additional episodes from the pilot] on our Atlanta show when Donald Glover’s Atlanta debuted. And then we noticed a marked fall off of interests at the network. It’s just one of those things where, unfortunately, a lot of white executives will think ‘Well there’s already a show about being black in Atlanta. So let’s move on.’ And our show went away. By the way, they would never feel that way about white people falling in love in Manhattan.”

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Exactly.

South Side’s journey into materializing certainly wasn’t easy and there were some dark moments, but the writing partners eventually had an epiphany based off Salahuddin’s real-life childhood friend who worked at a Rent-A-Center in Chicago. The two realized there was sort of a “tragicomic” allure to his story. This popped off the “entry point into the world of the series.”

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“We want to show you all different types of black people—there are people who would probably self-identify as hustlers, but there are a lot of, like, bougie black people on the show, as well,” Riddle noted. “There’s social activists, black people who just want to get the brand new pair of Jordans when they drop [...] everybody [is just] going [on] about their lives. That was the diversity in the black community that we wanted to highlight.”

From the jump, you realize South Side is delightfully black as fuck and Riddle teases more moments like that, including a song they wrote called “I Had Just Seen Him,” which illustrates the “black shock” of finding out someone died. I knew this would be a hard question, but alas, I always have to ask. So, I did ask Riddle, “What was the blackest moment you experienced on set?”

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“When we [were] shooting in Englewood, Harvey and even Hyde Park, people would wander up and be like, ‘Hey what y’all shootin’ here, this a movie? This Chicago P.D.?’” Riddle recalled. And according to Riddle, once they told them they were, in fact, shooting a new show about the South Side of Chicago, they’d always get one of two responses.

“‘Man, you know what the scene is missing? It’s me!’” Riddle laughed as he impersonated some of the passerby locals. “Or they would pitch ways you could change the scene—they were never shy—they would just be like, ‘Oh man this scene is cool, but my brother needs to raise the stakes and the antagonist [needs to do this]’ and you realize man, they are really smart [in regards to the craft of] storytelling. It was really blowing my mind.”

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Additionally, Riddle reflected on the beautiful kismet moments when the crew would discover talent from locals and, in turn, incorporate them into the scene.

“Every now and then, we would throw them in front of the camera and have a ball [because] we really wanted people on the South Side, specifically, to look at the show and be like, ‘Oh my God that’s so-and-so!’ [For] example, [we were shooting] a scene [involving a bus] and the person was a real bus driver. He made us laugh and so we turned the cameras on and got a few lines out of him,” Riddle said.

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South Side is Chicago as hell. Outside of Riddle (who spent multiple summers in Chicago shooting this show and has dubbed it his second home), the primary writing staff is completely Chicagoan, and mostly South Side, specifically. Whether it’s the insert of Beverly Woods (I legit let out a shriek when I saw it) or one of the characters mentioning she went to Kenwood Academy (seriously, this is how Chicagoans judge your personality—by the high school you attended), South Side is a lighthearted love letter to my city and I’m proud to see it.

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Plus, I’m of the mind that the more niche something is, the more universally it translates. And I believe Riddle agrees. Sure, this show is ensconced in the world of Chicago, but everyone will find something to relate to.

“It’s not like you’re going to watch this and feel like you’ve [been] transported to a foreign land. If anything you’re going to feel all the similar stuff that black folks do, we just give it different names depending on which region you’re from,” Riddle concluded.

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South Side hustles onto your television screens on Comedy Central, Wednesday, July 24 at 10:30 p.m. ET/PT.