Disclaimer: This story contains some spoilers for the first two episodes of “South Side” Season 3.
It’s a Chicago rite-of-passage to walk outside to get into your parked car, only to find out that your car is no longer there. It’s disappeared into an abyss most commonly known as the pound.
Specifically, if this happened while you were at happy hour, the club, shopping or experiencing any possible amount of joy in the downtown Chicago area, the car magically teleported into the underbelly of the city — a hazy, terrifying level of hell called the Central Auto Pound. It’s where you physically fall off the face of the Earth, because there’s barely enough signal down there for Google Maps to work. It’s also where you lose your last ounce of dignity as you stand in line for hours, begging them people to give your car back.
In Season 3 of HBO Max’s comedy series “South Side,” which premieres on Dec. 8, co-creators Bashir Salahuddin and Diallo Riddle, along with their super-funny cast and writers’ room, perfectly capture Lower Wacker and other Chicago experiences.
“What’s really crazy is, after we shot an episode down in Lower Wacker, about a week later I got towed,” Riddle told The TRiiBE. “I was down there and I had, like, a call sheet. I was, like, ‘hey, y’all. See. I was actually here last week. Technically, we’re business partners. Give me my car back.’”
Although Riddle isn’t from Chicago, Salahuddin and his brother Sultan — who is also a co-creator and writer on the show — call the South Side their home. Their experiences often drive the comedic storylines behind the episodes and its characters; of which Bashir Salahuddin plays Officer Goodnight alongside his wife Chandra Russell as Sgt. Turner, Sultan Salahuddin plays Simon (one half of the Rent-T-Own repo-duo) and Diallo plays flailing local politician Allen Gayle.
And what has truly made the show special in the hearts of Black Chicagoans is its universal relatability. No matter what side of the city viewers rep, there’s a character or running joke in each episode that embodies our shared cultural experience across the city.
“We really got lucky and have had some amazing writers, mostly from Chicago and mostly from the South Side — although, we do have the West Side, North Side and the south suburbs representing. We always say that our show loves the South Side, but our show really wants to represent all of Chicago,” Bashir Salahuddin said.
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“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.”
The guys came to Chicago on Dec. 6 for a WBEZ-hosted screening of “South Side” at the DuSable Museum. Hundreds of people packed the theater, laughing non-stop at the season 3 premiere.
We got a chance to speak with the Salahuddin brothers and Riddle during their “South Side” press run on Dec. 2. Read more of the interview below.
(This interview has been edited and condensed for clarity).
The TRiiBE: I’m really excited to talk to y’all. We’re big fans of “South Side.” Thanks again for this opportunity. I watched episode one (“College) and episode two (“Heartless). Is the world of “South Side” evolving in season three?
Bashir: We don’t want to evolve it. We’re a sitcom. We’re kind of like the Simpsons or what have you. We want folks to know that, when they show up, they ‘gon get the meal they love so much. I think with season 3, we just want to go bigger and better. We wanted to give all of our characters more. In season 3, we learn a little bit more about specifically the dynamic between Officer Goodnight and Sgt. Turner. We learn that Simon at his core, despite all of his talk and desire to be this heartless guy who makes all this money, ultimately he’s a sweet guy. We learn that Alan Gayle recently got his job as an alderman and, as Diallo puts it, ‘damn, he’s already tired of that damn job.’
I think one of the things we love about our show is that anybody who’s funny, anybody who makes us laugh, can be on the air. You have anybody from bus drivers to the guy in season 3 selling snow cones in episode 1. I literally met him selling snow cones on 80th and Vincennes. He made me laugh my ass off and I was, like, we gotta put him on the show.
Oh, so he’s actually from the neighborhood then?
Diallo: That’s right!
Bashir: 80th and Vincennes. Literally two blocks from Simeon [Career Academy]. That’s why I was, like, we gotta show that sign because people need to come get these snow cones. What’s nice about him is that he had no idea who I was. He was being himself and that’s what made it feel so special. This guy is just naturally funny everyday at this spot. We turned the camera on and, as is the case with most Chicagoans, especially people who come visit us or even walk past our set, they all are telling you they’re ready for the camera — and it’s true.
People always ask, what’s it like shooting in Chicago? And I think Diallo puts it best; “everybody who walks down the street or drives past says, ‘hey, man. The only thing missing is me!’”
So I’m from the West Side of Chicago. Even in watching “South Side,” I relate so much to so many of the narratives. In episode 1 of this season, where Rent-T-Own employee Stacy says, ‘you could’ve just rode the Red Line all day.’ People do just ride the Red Line or the Blue Line all day. Even the hotel in episode 2, the West Side has its own version of that seedy hotel.
Diallo: The very first time we went to Chicago to try and build this show was in the summer of 2016. There was a hotel near where Bashir grew up. We actually went looking for that establishing shot just because we were, like, that hotel looks so gross.
Bashir: You talking about the New Halsted [Motel]?
Sultan: Wasn’t nothing new about it.
Diallo: It was almost like they knew we were coming because they tore that thing down. So we had to find another hotel and actually the hotel we found was not that bad, but we dressed it up. Do you remember the name of the restaurant that’s in the bottom floor of the hotel we ended up using? It’s a famous place.
Was it Pearl’s Place?
Diallo: Yeah, yeah, yeah!
When I was watching the episode, I said to myself, that looks like Pearl’s…
Diallo: Let me tell you something. Pearl’s is fantastic. I always say I’m the interloper because I’m the one person attached to the show who did not grow up in Chicago. I was actually fascinated with the history of Pearl’s and all the people who came through there and ate southern food when they were on tour. So shout out to Pearl’s. I ordered from them on Postmates a lot.
Everything this season is a continuation of what we started off with so many summers ago, which is to show the authentic Chicago. That hotel left — well, that motel I should say — an impression on us.
[everyone laughs].
Bashir: Use the -M, brotha. Use the -M.
Diallo: We wanted to go back and use it but they couldn’t stay in business just long enough; so we had to use another motel.
Being Black in Chicago, there are so many stories. The story of “muff'ing” in episode 2, for example, how do you choose what to include and how to include it?
Bashir: First off, the thing that you’re seeing is, in any comedy, what you’re hopefully watching is the best of the best ideas that have been sort of stitched together and put into a story. So somebody goes, ‘hey, I have a funny idea about bed bugs.’ Somebody goes, ‘hey, I have a funny idea about Kareem keeps muff’ing Simon and Simon keeps falling for it.’ All of these things we laugh at and we talk about it, but we don’t know where they go. Then it’s, ‘oh, episode 2 could use a runner.’ And that runner is how we get into the story because he muffs him and he messes the kid’s egg up. I think Sultan, in your little mini group, were originally the ones who thought of that idea.
So for us, it’s really the writers. The answer is the writers. We really got lucky and have had some amazing writers, mostly from Chicago and mostly from the South Side — although, we do have the West Side, North Side and the south suburbs representing. We always say that our show loves the South Side, but our show really wants to represent all of Chicago. We don’t really want to play too much favorites because frankly, we as writers and creatives love all parts of Chicago.
Sultan: That’s right.
Bashir: I love going to Wrigleyville. I love the West Side, my mother’s from there. For us, once you have all these funny people in the room, the hardest part is trying to figure out how to make all of these different ideas come together but it starts with people who are really funny and who come with a wealth of ideas to share.
I love that. As a West Sider, it feels like the South Side always gets a lot of shine.
Diallo: [Comedian] Lil Rel is from the West Side. He’s just one of the many people who technically are from the West Side but they know that we got love for all parts of the city.
I love Lil Rel. I’ve been following him since I was in high school back around 2006.
Diallo: Can I give a shout out to his cousin, who is an amazing writer, named Rashida. And Rashida is a great writer in the room but also I was just recently reminded of [episode 7] that she pops up in, where I think she did a killer job going head-to-head with Sgt. Turner, which not many characters can do. She did a great job.
No spoilers but we’ll just say she’s a hip-hop authority who gets tested.
There are times on the show where you all seem to expand outside of the world of the South Side. We venture down into Lower Wacker, which I love the way y’all introduce that.
Bashir: What’s funny is that actually happened to me. I was visiting somebody downtown. Here’s the thing about Chicago street signs. You almost need a degree to know where to park, and if you don’t really pay attention, you think, ‘ah, my car got stolen.’ Yeah, it got stolen by the city.
So I went outside and I was like, damn! And somebody was like, ‘aye, they got you, bruh.’ And I was like, thanks. Thanks for letting me know that, kind citizen.
[everyone laughs].
Bashir: So when I went down there to the Central Tow Lot under Lower Wacker, it really felt almost mystical. It was, like, we gotta shoot something down here. It’s so crazy. And lucky for us, much like Lollapalooza in our season finale, the City of Chicago was cool. They were, like, ‘y’all wanna shoot down there? No problem.’ So we ended up getting some really fun stuff down there.
Diallo: What’s really crazy is after we shot an episode down in Lower Wacker, about a week later I got towed.
Nooooo.
Diallo: So I was down there and I had, like, a call sheet. I was, like, ‘hey y’all. See. I was actually here last week. Technically, we’re business partners. Give me my car back.’
[everyone laughs].
They do not play down there.
Diallo: I didn’t get my car back for a day. It was terrible.
I have to ask this question about Sgt. Turner and Officer Goodnight. I love the way y’all creatively have them as characters, especially in a city like Chicago where we all have terrible relationships with the police.
Bashir: Yes, of course
How do you find ways to tell the stories of police officers in a place like Chicago and especially in a place like the South Side? Sgt. Turner, to me, is like if my cousin got up and decided to join the force.
[everyone laughs].
Bashir: Sultan and I have police family. Without blowing them up, we had aunties and uncles who were on the force. This is the 1980s now. They would tell us wild ass stories. We would be sitting there going, ‘are y’all on the side of the law or are y’all just people who wear uniforms and get shit done?’
Of course I don’t want to dismiss them because frankly I don’t really have any interest in shining a negative light on anybody. We want to be funny. That’s the most important thing.
Sultan: That’s right
Bashir: So in terms of the approach to Goodnight and Turner, it’s really about us saying what’s the funniest way to make these characters just human beings who have problems. With Turner specifically, I just remember walking down the street and seeing a woman cop and her hair was laaaid. I was, like, only in Chicago. I was, like, I bet she don’t get out that car unless she has to. She don’t want to deal with these people. And that’s an energy that I think all of us, especially Black folks, will understand. I don’t wanna deal with this shit. So that really came from a really personal place, from our family who were cops and we just grew up being, like, ‘yo, that’s crazy what you just told me. I’m gonna pretend like I didn’t hear it.’
Chandra herself, she really brought a lot to that character. I would say she probably created that character and her performance was far more than what we did in the writers room, which she’s also in.
I know we have to wrap up soon. What is the frosting cakes story in episode 2 really about?
[everybody laughs].
Who are y’all exposing? At first, I thought it was the Girl Scouts. But it got too deep and I thought, maybe this isn’t about the Girl Scouts.
Bashir: It’s not the Girl Scouts. And I hope their lawyers don’t think that. When we do anything in the writer room, it really is what’s the funniest story we can tell. We know that Kitty and Goodnight’s relationship is hilarious and problematic. And somebody in the writer’s room said, ‘what if Kitty joined a cult?’ And we tried to think about what kind of cult could she join. I think we were originally thinking about a Mary Kay cosmetics, kind of multilevel marketing thing.
Like, AVON?
Bashir: Very much like an AVON. AVON is probably where we were, like, ‘that’s something that we know.’ We all had them cousins and uncles who would come and say, ‘aye, man, I’m selling knives.’ We all know those people. But I think ultimately we landed on frosting because we had never seen that before. In our storytelling, in our writers room, one of the best ways to have your idea really stand out is for something nobody has ever seen, and nobody has ever seen a story about frosting but it is not for cakes.