On Dec. 8, South Side returns to HBO Max for season 3, bringing more antics from Simon (Sultan Salahuddin), Kareme (Kareme Odom), police officers Turner (Chandra Russell) and Goodnight (Bashir Salahuddin) and the rest of the team at Rent-T-Own in Chicago’s Englewood neighborhood.
“We really wanted to deepen the audience's sense of who our more regular folks are,” co-creator Bashir Salahuddin tells LA Confidential over Zoom. “And I think for us, we ended up having so much fun on set… We spend more time with the characters who have been there since day one.”
“One thing our show does is you might meet a character at their workplace in one episode, but then the next time you see them, they're out with their family,” co-creator Diallo Riddle adds. “We populate the show with these characters. And by the way, we have very strenuous debates and conversations about, ‘Well can that character be this person in this scene?’ Like, ‘Yeah,, maybe they were a cop in that scene, but we never said that they weren't a single mom.’ And then we'll put them in another scene. So we've built out the South Side… as our Springfield.”
The new season is South Side’s biggest yet. Across the 10 episodes, you’ll find guest stars like Chance the Rapper, Vic Mensa, Cordae, Chicago Bulls player Ayo Dosunmu, Lahmard Tate and Adele Givens. They also went high concept with an episode that pays homage to The Dark Knight trilogy, a Kwanzaa holiday special and an episode set at Lollapalooza.
Still, comedy is always at the center of the show.
“One of the episodes this season is just about our character Officer Turner, played by Chandra Russell, just trying to go to a birthday dinner with her family,” Salahuddin says. “We challenged ourselves: ‘Can we write an episode of South Side that is as funny as usual and mostly takes place in a room around the table?’”
Read more from our conversation with Salahuddin and Riddle below.
Bashir, you’ve said season 3 is some of the best work of your career. Why is that?
Bashir Salahuddin: I think that we are in a space where between Diallo Riddle and Michael Blieden and myself and our other writers, we're looking at probably over 50 years of experience collectively with television making. When we first started in this business, we would work with Lorne Michaels, and he would always say the interesting thing is that it's a shame that shows are only given one season or so to really find themselves. Because in his experience, he feels like it takes a couple years for a TV show to really figure itself out. Certainly one of the shows we model ourselves after is The Simpsons, and I would argue that once they hit season 3, that's really where they found that other gear that made them an international phenomenon. I think for us, we're feeling so much confidence about our stories and our characters and about the world, we really are figuring out what are the funniest pieces to put forward for each character.
Our cast and crew, they all came back so excited and eager to be a part of getting to do this again. And for us, it's so much wish fulfillment. So we put everything in the kitchen sink in the season, and I think fans are gonna be better for it.
Especially with comedy shows, you have to rely on process. The process of a comedy show can be a little scary because you have to start every season knowing nothing. All you have is a bunch of folks sitting in a room, throwing story ideas at each other, filling up a wall full of pieces of paper with tidbits and words and things that could be funny. Not to compare us to the 1990 Chicago Bulls, but I do feel like our team has played together for so long that we're starting to know, if I throw this out, this person is going to catch this rebound. I give it to this person, this writer is going to shoot a great jump shot.
You have an episode set at Lollapalooza. What was it like filming at the actual festival?
Diallo Riddle: We said it was controlled chaos.
BS: I loved it. I just looked at this picture the other day. There is a photograph of all of our cast and crew gathered under the expressway like a mile from Lollapalooza. We had all this stuff we got to stage and we can't do it on the grounds. I just want to, again, thank Lollapalooza. They were so generous and so cool. They said we had all access. They said, “Look, the fans are here to hear music, so you have to be aware of that.” But the fans were cool. We didn't block anybody's view. And in fact, one of my favorite things is the South Side thing—we always cast people off the street.
There are folks who just showed up at Lollapalooza that morning as concert goers who are now going to be prominently featured on our show. We couldn't be happier. And then also Cordae the rapper, he and his whole team chose to dive in headfirst of this idea we had. And so he actually plays a major part in the episode and he actually kept going during his set, which was incredible and more than we could have asked for. So Lollapalooza was insane. It was crazy. It was very hard, but that's something that our show really embraces. We love the challenge. Anytime something looks daunting, we're all up for it. And I think the audience is gonna love that Lollapalooza episode. I think it's a love letter to Chicago too because the whole thing is right in the middle of downtown. So there’s all this beautiful photography where you see this gorgeous Chicago architecture framing everything. I think that's one for the ages.
You also have a Kwanzaa episode. Is there a special approach you have to take when it comes to developing an episode that's a holiday special?
BS: I was born and raised in a Muslim family and I remember that there were times when I wanted to use like an Islamic term or a Muslim name. And when we were at Comedy Central, we'd get a phone call: “Woah, woah woah. Hey, guys. What's this about?” And I'm like, “This is my cousin's name. Calm down.” It's our experience. And so with Kwanzaa, I celebrate Kwanzaa. For us, it was a joyful thing to have this thing, which we already celebrate, and then have fun within it. And I think fans are going to be surprised that we don't really make any jokes about Kwanzaa itself. It's more this really fun, festive series of crazy events that happen in and around the celebration and so forth. But also you learn about celebration too because we actually have this one cool storyline that actually teaches you the principles of Kwanzaa and it's literally the silliest way possible.
DR: My family knew the founder of Kwanzaa. I would say our relationship with Kwanzaa is a little bit complicated because it's like if you grew up friends with L. Ron Hubbard or anybody else who started a religion recently.
Kwanzaa has been used many times as just sort of a punchline. But we're like, “What if we actually did a holiday special around Kwanzaa that actually taught you what Kwanzaa is actually about and is not just a throwaway joke?” I feel like we've more than accomplished that. And actually even to somebody like me who thought I knew a lot about the principles, it’s actually really inventive, not even just from a principle point of view, but visually, I think we pulled off some things that I would have never thought we could pull off on our show about the South Side of Chicago, including an extended music video with a pretty amazing Kwanzaa visual at the end of it.
Do you have an episode you’re most proud of this season?
DR: Michael Blieden has done an amazing job. He's directed all but maybe four episodes of the show. But I am pretty proud of an episode that Bashir and I directed. It's not a parody of The Dark Knight by Christopher Nolan, but it is a little bit like “What if Christopher Nolan directed an episode of South Side?” That was our mission statement going in. And I think that we just got an amazing story, sort of a heightened version of the world of South Side with some great performances. We check in with almost all of our cast members on our show, which is not something we do every episode, but everybody pops in, even briefly, in that episode. It's just a lot of fun. We got to shoot in Lower Wacker, which is where your car gets towed when you park almost anywhere on the street here in Chicago. We shot some action scenes on a bridge with a character jumping off of a bridge. It was our chance to live out our action comedy dreams, growing up as kids in the ‘80s. We just got to try some things that really were inventive and stunt coordinator-centered, and that was just so much fun.
This interview has been edited for length and clarity.
Photography by: Courtesy of HBO Max