south side

South Side’s Showrunners Talk Tapping Into Chicago’s Funny Side

South Side showrunners Bashir Salahuddin and Diallo Riddle, who also play supporting roles on the Comedy Central series. Photo: Corey Nickols/Getty Images

Chicago has been deemed a city of untold violence in the screeds of nightly-news and right-wing pundits, but there’s much more to the beautiful, complicated city than what headlines suggest. The Comedy Central series South Side seeks to disrupt the usual perception of the city, using a sprawling cast — anchored by recent community-college graduates and hustlers Simon (Sultan Salahuddin) and Kareme (Kareme Young), who work at a rent-to-own store doing deliveries — as a lens to explore the humor and diversity of experience that makes up the titular swath of the city. After struggling a bit in the first few weeks to find the right balance in its comedic approach, the show hit its stride in its sixth episode, “Mongolian Curly,” which proves to be something of a turning point: The humor becomes more specific and cutting, and the characters gain surprising complexity. In essence, the show is really finding its voice, which it will get the opportunity to develop further, as South Side was just renewed for a second season.

Showrunners Bashir Salahuddin and Diallo Riddle, who also have supporting roles on the show (Officer Goodnight and Allen Gayle, respectively), originally met when they were students at Harvard, bonding over their shared love of Coming to America and shows like The Simpsons, whose earlier seasons provided great inspiration for the multi-hyphenate creators. After working on Jimmy Fallon’s late-night talk show and a near-miss with an HBO series focused on Diallo’s hometown of Atlanta, the duo turned their attention to Salahuddin’s hometown: Chicago. That’s where I recently sat down with the two of them, on a bright afternoon at a hotel downtown, to talk about drawing on the experiences and performances of real Chicago residents to show a different side of the city.

This interview has been edited and condensed for clarity.

What inspired you to do a project about Chicago?
Bashir Salahuddin: We always wanted to do something based on our hometowns. When [the HBO series] didn’t pan out, we turned our attention onto my hometown of Chicago. Simultaneously, my brother had been telling me that I need to talk to his friend Quincy, who I grew up with and is also really funny guy, him and his twin brother. Quincy used to work at Rent-A-Center. Spent ten years there. “He has stories. He has stories for your ass.” [Laughs] All this sort of subterfuge and drama in it. It made us realize, “Wait a second. Chicago is a city we want to crack.”

What’s nice about using the rent-to-own model is that because they’re delivering and picking stuff up, and this vehicle allows us to go all over the city, now we can do something we’re really excited about, which was: We’ve always wanted to take Chicago and turn it kinda into Springfield from The Simpsons. We have 150 speaking parts. Why did we do that? When you ask someone who the funniest person in their life is, they’ll oftentimes name a big comedian, but also often times they’ll offer “my auntie,” “my cousin,” “my mother is the funniest person I know and she’ll make you cry laughing.” Our thought was, we’re educated enough in comedy to create an infrastructure to give these people the ability to shine. But let’s put those people on camera, those funniest people. Most of the other folks you see on camera [besides our main stars] haven’t acted before.

Diallo Riddle: Local actors and absolute neophytes.

They’re very comfortable in front of the camera.
Diallo Riddle: I think that speaks to the fact that people in this city aren’t shy. In fact, there are so many times we were shooting with brand-new actors in front of the camera and people would wander up to the shoot and would be like, “This is a good scene, but you know what it’s missing … me.” [Laughs]

Bashir Salahuddin: It was very important for us to bring the camera into the South Side. This actually ties to why we do this show, because the city of Chicago as it’s portrayed on the nightly news was not the entirety of my experience — it was a very small piece of my experience. My experience was largely positive and wonderful and joyous. And the people I knew growing up were supportive and loving and there was a community aspect to it, and there was also an aspirational nature to it. Everybody I knew had a side hustle and was trying to do better for themselves, and we didn’t see that represented anywhere. We said that there are enough places in the world to show the challenges of Chicago. Let’s be the place where you can experience the joy and the love and the laughter. Also just the raucous, hard-edged South Side humor I grew up with. It was really important for us to stay focused on the funny. At its core, we’re spreading joy by letting the city of Chicago speak for itself, so in front of and behind the camera I would say 90, 95 percent of the people are from Chicago.

What are some specific things you knew you wanted to avoid in your depiction of the city?
Diallo Riddle: One thing we decided on pretty early is that even when you see Shaw and his gang, for lack of a better term, we didn’t want that to be the headline of the show. If you notice, we never explicitly say what makes them even a gang. You get the sense that there is some menace there, some intimidation, but we never show them actually selling drugs or any of that kind of stuff. We went out of our way to not show the traditional drug-selling plotline or the traditional gang-war plotline. We didn’t even want to go down the path of making the gang members anything like one-dimensional characters. Because I feel like if you ever take a look at black people as a whole, we’re way more interesting and non-stereotypical than we’re frequently portrayed.

One of the things we both loved when we first met is the movie Coming to America. What we appreciated about that movie, and why we come back to it time and time again, is you see rich people, you see poor people, you see criminals and you see saints. You see the true diversity within our community. And for this show I like the fact that we can see characters like Uncle Spike, who are dabbling in some crazy stuff, but you can also have the alderman. We just wanted to show a little bit of everything, and we didn’t want to waste much time with the stuff you already get from everywhere else.

Bashir Salahuddin: Diallo and I will often say about our experience, black folks already live poignant lives, they don’t have to come home and watch poignant television. Sometimes it’s okay to be escapist. Not escapist and being fake, but just embracing the joy.

Diallo Riddle: Real life is funny sometimes!

Bashir Salahuddin: We pulled a Larry David and told our writers, “Tell us stories that actually happened to you.” We did have fun and take liberties, like all good comedies do, but everything started from What’s the thing that happened to you that we can make fun of?

Diallo Riddle: Our writers’ room is based more on “what happened” than “what if.” And there’s a power in that. There’s so many funny stories that came out of that room that didn’t even make it into season one.

Bashir Salahuddin: I love when I can watch a show and know I can let my guard down while watching it. In some way you are putting ideas and images into people’s consciousness. You have to be careful — it’s a trust.

Bashir Salahuddin: I have a spiritual point of view about it. I actually feel blessed I have a sense of humor and my family is funny and my friends are funny. I think people’s lives are really difficult sometimes. I think it’s a blessing if you can lift some of that and put a smile on people’s faces.

Diallo Riddle: At the same time, there are scenes I am so proud of that do make a commentary on the world without doing so in a way that feels like the comedy writers stopped what they were doing and wrote a serious paragraph. Like the character Bluto, when he’s at trial and says, “There’s nothing more expensive than being poor.”

I like that line a lot. That is very true.
Diallo Riddle: It’s true! He’s talking about parking tickets, but at the heart of our show is the predatory lending of rent-to-own places.

One thing the show is really good at is weaving in Chicago traditions, specifically black Chicago traditions, like stepping and mild sauce. 
Bashir Salahuddin: In the writers’ room, we made sure that outside of two or three people everybody’s from Chicago, most of them from the South Side.

Diallo Riddle: I’m the anomaly in that scenario. [Laughs]

Bashir Salahuddin: Let’s not make the setting incidental, let’s make the setting a character. People have a point of view about the South Side. For me, never knowing if you’re going to get more than one season, I’m like, “I have to do something with stepping.” It’s something unique and specific to Chicago. Spades is not specific to Chicago, there’s spades all over, but my experience with spades is intense and formed by Chicago. Mild sauce is a very Chicago thing. The fact that when people introduce themselves on the show they say what high school they went to and what intersection they live near — that’s it. When we start to accumulate those specific touches and the writers provide us with those, we flesh out our world. The model we create becomes much more authentic. Because the parts are spoken into reality by people who lived it and they’re telling you about things they’ve seen with their own eyes.

I want to talk a little about the upcoming eighth episode, which deals with a young black girl’s coming-of-age story in an inventive way. I really loved how it chased joy, and I want to watch more of regular black people experiencing joy. 
Diallo Riddle: Credit to Michael Bleiden, who directed every episode. We met him at Fallon he’s been a friend for years. Especially in that episode, I felt there were a couple of shots that were lyrical. And you don’t usually see that in comedies, especially the black ones.

Bashir Salahuddin: Got a little Terrence Malick going on.

The writer Alisha Cowan, she pitched the idea saying she wanted to write a story about a little black girl who goes to find herself. I had never heard of anything like that. She said, “No, you’ve never seen a black girl who wasn’t in serious fucking peril. She’s just going on a spiritual journey.” We don’t get to take a fucking break. We really tried to make sure as EPs — one thing I am most proud of with Diallo, Michael Bleiden, and myself is that we really know what we don’t know. We really knew in that specific episode it was important to try and find support for the architecture, to provide support for what the plot is going to be, but essentially put wind behind Alisha’s sails. She was trying to make sure she was telling the story in the correct way, writing about the experiences of a young black girl who grew up on the South Side of Chicago, and it’s something she wanted to see when she was growing up.

Bashir, let’s talk about the character you play, Officer Goodnight, because I wasn’t sure where you were going with his arc. 
Bashir Salahuddin: We do have some arcs, some light arcs. I would argue that in season one it’s just learning more about these characters. But here’s where it starts: with him really wanting to be great, really wanting to be a detective, and really hating the South Side. For me, Goodnight functions a little like Uncle Ruckus on The Boondocks.

I can see that.
Bashir Salahuddin: His job is to provide, “This is the thing people say about you that I’m also going to say.” Everything bad about the South Side you see on the news — Goodnight believes that’s all there is. I don’t want to move him too far from that. But there are little glimpses where he realizes he’s wrong. There’s a great thing in episode six, which we don’t really lean into, when he’s walking around South Shore and he’s like, “It’s not too bad here,” and he’s having a little snow cone. What we’re not going to do is, by season three he’s in love with the South Side. I think it’s important as writers to keep him where he is. And where he’s going to be is he hates the South Side, everyday is a nightmare and he feels trapped. And the reason why he feels trapped is because that’s something we give all our characters. It’s really unfortunate but also super realistic that people get trapped in their past and their circumstances.

The last thing I’ll say about Goodnight is that the reason he adopted a white kid is something I am really proud about as a writer, and I don’t know when we’re going to reveal it, but it’s not exactly what it appears.

It’s interesting to see him put in situations where he has to face his own internalized racism and the fact that other people know about it. 
Bashir Salahuddin: This director told me recently, “Your character doesn’t know that about himself.” I got to cut my writer ring off to be a better actor. You can’t be a writer and actor at the same time.

Ultimately, what do you want audiences in and out of Chicago to take from the show and the world you’ve built?
Diallo Riddle: That there are humans that live in these communities. I think it’s important to humanize people and to make clear — no matter what your zip code — you go through a lot of the same things. And look, there is violence in every community. But it’s important to remind people there’s a lot of love, a lot of laughter, and a lot of life on the South Side.

Bashir Salahuddin: When you go to other places when you’re from Chicago, people say, “You made it here. You’re alive?” If we can chip away at that falsehood and people are like, “You’re from the South Side, you must be funny, you must be interesting” — as we highlight parts of the South Side and people who live in Chicago, especially black Chicago, and as we show you the diversity that they have, that the people themselves will self-identify, “Oh, these are the things people know about us. Oh, people know we’re funny.” ’Cause right now the world doesn’t know we’re funny. When we hear about Chicago comedy you think Blues Brothers, you think of Second City, you think the movies of John Hughes — all hilarious, wonderful stuff that I support—

Diallo Riddle: Very North-centric.

Bashir Salahuddin: Very downtown-centric. We got Bernie Mac, we got Robin Harris, we got Sherri Shepherd, we got DeRay Davis, we’ve got these hilarious people. If the city’s self-identification, the South Side’s self-identification, could be more joy, more just being funny as hell, then I think we’re doing something right.

South Side’s Showrunners on Celebrating Chicago’s Funny Side