Sultan Salahuddin as Simon James, Chandra Russell as Sergeant Turner, Kareme Young as Kareme "K" Odom in Comedy Central's South Side | Photo courtesy of Comedy Central

When HBO axed “Brothers in Atlanta,” a comedy created by native Diallo Riddle and his writing buddy Bashir Salahuddin that had been in development from 2011 to 2016, Atlanta’s loss was Chicago’s gain.

Instead of throwing in the towel, the duo turned their attention to Saluhuddin’s hometown, the South Side of Chicago, which became the foundation for their hilarious Comedy Central show, South Side.

“Coming out of that painful [HBO] experience, we were, like, ‘Look. I’m from Atlanta. You’re from Chicago. We need to tell the Chicago story now,’” Riddle says, recalling the conversation he had with Salahuddin after HBO halted their show. 

“So at that point, we started developing a show with Comedy Central about Bashir’s hometown of Chicago,” Riddle says. “And so, when we hired our writers, we made sure that everybody was from Chicago.”

South Side, which premiered on Comedy Central in July, follows two recent community college graduates, Simon (played by Salahuddin’s brother, Sultan) and Kareem (Kareme Young). The accomplishment encourages them to leave their jobs at the local Rent-T-Own, where they spend their days repossessing microwaves, and XBox game consoles from residents behind on their payment plans. But both quickly realize that leaving their jobs will be harder than they thought.

The comedy’s portrayal of its namesake is self-aware and witty, but it also manages to humanize Chicago’s South Side and its people in a way that’s unique to television right now, which is brimming with varying dramas such as Showtime’s The Chi and Dick Wolf’s Chicago Fire, Chicago P.D. and Chicago Med franchise. 

“Our approach to comedy has always been that we wanted to tell a hard comedy about cities that people don’t really understand. But once we translate it for them, they’ll understand, like, ‘Oh. This is a universal thing,’” Riddle says. “What you call your friends, it might be ‘shawty’ or it might be ‘joe.’ Those kinds of things change, but Bashir and I always knew that we knew how to tell a story, and we knew how to tell a story humorously.”

Currently in the middle of season one, South Side airs every Wednesday on Comedy Central. The TRiiBE spoke with the multi-hyphenate Riddle, who created, produced, wrote and stars in South Side alongside Salahuddin, about the style of authenticity their show brings to Chicago. 

The following has been edited and condensed for clarity.

You mentioned that you wanted to show the South Side of Chicago in a different light than how it’s usually presented in the media, but the show also doesn’t sugarcoat anything. We see cops taking bribes and Rent-T-Own employees repossessing a microwave. How do you walk the line of funny and real?

Riddle: Honestly, we’re just trying to be funny while telling the truth. We try to never self-censor. We go out of our way to say, ‘Look. This is kind of messed up but we grew up in these communities, and we think it’s kind of funny.’ We went out of our way to have this writers room where essentially we’re replicating the big, Black families that Bashir and I grew up in. We went out of our way to cast Chicago people, put them in front of the camera, because that’s just another way we felt we were making the show really authentic. They have love and have pride in their community. If you just believe what the politicians and the media have to say about the South Side, they’d have you think that everybody down there is trying to escape. Like, this is Syria right about the time that the regime was falling. It’s the opposite. It has challenges, but they love the South Side. Now we’re giving, hopefully, the entire world a more clear picture, a more robust picture of why people love the place they call home.

As an Atlanta native, what’s it like writing such a Chicago-specific show?

Riddle: My main role, as the one guy from Atlanta, was just to be the outsider. I spent three summers in Chicago working on this project before we ever got to air.  I’d just ride around with Bashir and be like, ‘Hey, what’s that?’ or ‘What did that person just say?’ My role was to point out to him, and to our Chicago natives, ‘Hey, as an outsider, this is really interesting to me.’ Our roles were reversed on the HBO show because on the HBO show I was the person from Atlanta; Bashir was not. Sometimes you just need one person to have an outsider’s point-of-view and let others know, ‘What y’all are working on right now, this is dope.’

Diallo Riddle as Allen Gayle, Sultan Salahuddin as Simon James in Comedy Central’s South Side | Photo courtesy of Comedy Central

There was a lot of backlash with Showtime’s The Chi because they filmed some scenes on the West Side, though the show is based on the South Side. Did that affect your decision-making at all?

Riddle: I wasn’t really aware of that. But I also want to say that Lena Waithe, [the creator of The Chi], is a friend. I’ve always rooted for Lena’s success. I think it’s so hard to get a TV show on the air. Bashir grew up on 83rd and Emerald. He wanted to make sure that we shot on the block of 83rd and Emerald. That was really important to him. Chicago is not a forgiving city in the sense that if they think you’re faking it, they’re not going to appreciate it. I learned that pretty quick. They appreciate that our writers are from here, that our actors are from here. All of that stuff is really important.

You made a point to cast Chicago actors, but you also cast South Siders who had never acted before. What led you to that decision?

Riddle: I’ll put it like this: When you talk to people who don’t work in this business, and you say, ‘Who’s the funniest person you know?,’ they don’t usually say some stand-up comedian or some actor from TV. They usually say, ‘Oh, my auntie. She’s really cool. She has all of us laughing.’ The way we cast this thing is we literally went and found that auntie and put her on TV. There was a scene in episode three that takes place on a bus, and the actual bus driver had us cracking up in between takes. And we were, like, ‘Hey. Put the camera on this guy for a little bit.’ What we wanted to do was find the people in the community who were just funny people and give them some screen time. You get a really authentic, organic performance out of somebody who hasn’t been overtrained or isn’t a Shakespearian actor putting on a fake accent.

What’s the feedback been like?

Riddle: It’s been great. The show remarkable has gone up every week in the ratings. The show is sitting at 100% on Rotten Tomatoes, which means we haven’t gotten one bad review. Not one. I think that speaks to the fact that we work really hard on the show, and critics like it, and more importantly, people like it. I get the sense that people who watch the show really enjoy the show. In some ways, that actually means more to me than the critics.

What are some tips for creating a well-rounded show that authentic to its people and place?

Diallo Riddle | Photo by Leslie Alejandro Photography

Riddle: I don’t want to play the game of, ‘This show’s the real Chicago.’ I think we’re not doing a Dick Wolf show. Whether it’s The Chi or the Barbershop movies, there are always going to be people who use Chicago as a setting. I just think we use it as a setting for the comedy of Diallo Riddle and Bashir Salahuddin. So I wouldn’t say that our show is more Chicago than others. I just think that our show is a very Chicago show. We went out of our way to get very specific with the details. We’re going to be specific with details that other shows aren’t aware of or wouldn’t think to spell into their shows. I am happy that we are a hard comedy. We’re not a dramedy. There’s never going to be a special episode of South Side where someone buys a gun and goes and kills somebody. That’s just not happen. We’re going to do a show that hopefully makes you and your of-age family laugh.