Diallo Riddle and Bashir Salahuddin know that having their own show is an opportunity that neither of them can waste.
The latest proof of their longtime comedic partnership is Season 3 of “South Side,” the hilarious workplace-adjacent comedy that began its life on Comedy Central and now resides on HBO Max. The show follows RTO, an Englewood-area rent-to-own store, as their employees travel through the greater Chicago area, repossessing furniture and getting caught in the wildest, weirdest corners of the city. When Salahuddin’s Officer Goodnight isn’t somehow wrapped up in those same schemes and scuffles, he’s one of the many characters on the show who gets a full (and sometimes very confusing) life away from their job.
One way to juggle all these different people and ideas is to throw as much into the mix as possible. Over the course of a single conversation, Salahuddin and Riddle mentioned all of the following as touchstones, comedies they admire, or work that their shows share at least some DNA with: “The Pink Panther,” “The Simpsons,” Mel Brooks, “So I Married an Axe Murderer,” “Bill and Ted’s Excellent Adventure,” Ben Stiller, “Star Trek,” “My Dinner with Andre,” the Austin Powers movies, “Trailer Park Boys,” and in Riddle’s words, “whatever weird song or weird science fiction book or TV series that we’ve been into lately.”
And there are plenty of jokes that exist on their own and don’t have an obvious line to connect them to an influence. (Though, some of the best episodes of “South Side” have been longform riffs on beloved movies.) The result is a series that has always had an unmistakable, welcome, go-for-broke attitude about each new episode. The same is true for “Sherman’s Showcase,” the wildly funny IFC sketch show that Riddle and Salahuddin head up and co-star in. You get the feeling that, from the instincts of Salahuddin, Riddle, and their many comedic partners on “South Side,” there’s a constant effort to pack in as much as an episode can hold.
“When we first started working, we were in this writer room. And every day at six o’clock, one of the showrunners was like, ‘Alright, guys, come on. Let’s just wrap this up. We’re gonna be here all night.’ And we were thinking, ‘Well, isn’t the goal to make this as funny as possible?’ The funniest thing might be something we discover two hours after the room is over,” Salahuddin said. “We want fans to laugh so hard that the show moves fast and they kind of look up and go, ‘Wait, that’s it. It’s over?’ We love to have people just be breathless.”
With that as a guide, Riddle and Salahuddin are steering the ships on two of the pound-for-pound funniest shows anywhere on TV. Naturally, that’s a process that doesn’t happen without a lot of work and some strong collaborations along the way. The pair of stars/writers/showrunners talked with IndieWire about harnessing some of that “South Side” Season 3 magic.
IndieWire: There are some “South Side” episodes where I can imagine the starting point was something simple: “Kitty joins a cult” or “Greg goes AWOL.” But Episode 3 of Season 3 is one where I’m not sure how that would have started.
Bashir Salahuddin: The rule is that every single episode must be able to stand on its own and be enjoyable. If you have never seen any other episodes, you can watch the first episode this season and enjoy it. But there are things we put in there for ourselves, little easter eggs, little moments. Last season, we painted a mural of Diallo’s character in the basement. That mural is still at play when Greg is down there doing push ups. It just becomes our way of decorating and fulfilling the sense of lore around the show, that the things we do actually do matter.
Last season, we did an episode about fear where Simon and K are repo-ing from this dude. He’s telling Simon all this stuff about how to deal with his own problems. Simon leaves and the guy looks in the mirror and goes, “I used to be afraid of clowns. And now I am the laughter.” And he smears white paint on his face. At the time, we had no idea what that meant. It just made us laugh that this dude was waiting until everybody left, talking in the mirror and starting to make himself up. But then we started to think, “Well, maybe the Laughter is like an organization.” We love the movies of Christopher Nolan. Chicago is often Gotham for the Batman universe. And so for us, we began to put two and two together. There’s an unseen, over-the-top bad guy who everybody’s hunting. Why don’t we do our version of a Batman movie? So it really wasn’t anything that anybody came in the room with fully baked. At some point, you step back and go, “Holy shit, this actually all fits together. This is a really cool puzzle.”
Diallo Riddle: We got to direct Episode 3. From a directing point of view, there are two scenes that really jumped out to me. One is the scene where, no spoilers, a certain character jumps off a bridge into the Chicago River. From the time that scene was written. I was like, “Bashir, we have to direct this episode.” We grew up in the ’80s and that genre of action comedy. I just wanted to shoot something where Goodnight chases a man, he gets to a bridge, and he decides to jump off the bridge. Both of us were reveling in every fine detail. After our art department figured out how we would shoot that scene, it was exciting to discuss how we were going to do the graphics package part of the scenes. It looks so real.
BS: They killed it. I’m very impressed.
DR: And it’s a beautiful part of the Chicago skyline! The other scene I always think about has me Bashir, and Quincy at a counter. We do this shot over the shoulders of two of the characters and find a woman in the background and she does this amazing thing. Full disclosure, I had just recently watched the horror movie “It Follows.” That movie is full of those weird ’70s zoom-ins on a character the background, but when you find them in the background it’s terrifying. Those two moments, they were so much fun, and I get happy every time I watch that episode.
Bashir Salahuddin in “South Side”
Adrian S. Burrows Sr./HBO Max
How sad are you that the giant Simon head had to be destroyed in that episode and that you couldn’t hold onto it?
BS: Well, let me tell you something you don’t know, brother. There are three of those heads. I’m wondering where they are because somebody has access to that head. And whoever does, I hope it ends up being something in somebody’s house one day, and they never explain it. People just look at it and go, “What the hell is that?” “It’s complicated. Don’t worry about it.”
Our production designer probably has a treasure trove of cool props. But also a lot of stuff goes into storage and then it just waits to see if we’re gonna have another season. Last season, we ended it with this Pyramid. And our art department is so nice. Our production designer Natalie Groce, she made baby Pyramids for a lot of people, so I actually have a little baby Pyramid made of leather.
DR: I thought you were going to say you had The Pyramid. Turn it into a man cave.
BS: The idea is it’s a pyramid, but it’s the perfect four-person couch. It just happens to be a pyramid shape. Which makes no sense, but we were just laughing at it. Diallo, me, and [director/writer] Michael Blieden, we’re lucky in that all of us have spent time in rooms where we were told, “Oh, that’s too silly. That’s too weird.” Now it’s us looking at each other going, “Oh, that’s not silly enough. It’s not weird enough. Go further.”
With “South Side,” I feel like there’s an effort to not only go further and fit in a bunch of jokes, but really go for a lot of different kinds of jokes. There are a few that fly by before you really even have time to register them.
BS: It’s really a testament to the writers. We have writers who have different sort of strengths. There’s somebody who’s really good at punchlines, somebody who’s really good at scenarios, somebody’s really good at making dialogue funnier. You have all these different people come together and then we form like Voltron. You really feel lucky to go to work with them every day because you know they’re going to be giving you stuff that you never would have thought of yourself. One of our writers came up with one in the scene in Episode 1 where the guys go to the motel for the first time. The guy at the front desk goes, “Hey, this is Helen. She used to be my sister,” and he just blows right past that. I was watching it with some people yesterday, they were like, “Wait a second, ‘She used to be my sister.’ What does that mean?” And I’m just laughing at it because that’s how I felt about it. I have no idea what the hell a used-to-be sister is. I don’t even know how that works.
DR: I’m thinking about two writers in particular. Will [Miles] is amazing just coming up with a hard joke. It doesn’t even need much setup, but he just comes in with it. And then Rashida [Olayiwola], I feel like sometimes, she’ll just come up with a funny way to say something. It’s not that the line is a joke so much as it’s funny the way that it’s articulated. And I think that that is one of the things I really appreciated about the room. Bashir and I have been in enough rooms at this point, that we don’t always have to say the most. But when we say something, it usually has some impact.
BS: I think I’m really good at knowing how to keep the comedy coming in and not cut it off, and not saying something that will make somebody feel shy about pitching. You can have rooms that have really strong personalities in them. And in some writer rooms, those personalities tend to do more stuff. But it doesn’t mean that the super quiet writer at the end of the table isn’t funny, right? What I love about our room is that the people who are loud and pitching all the time, they get their stuff in. But we also really encourage the folks who are only gonna say one funny thing all hour, but it’s the funniest thing anybody said all hour.
You mentioned always wanting to go weirder. “South Side” is great at suggesting or only showing a little slice of something. I feel like that’s what Episode 4 does. Seeing that one little scene in the basement like tells you everything you need to know about this new rich family.
BS: I have more questions than anybody about who they are. What’s interesting is one of the guys in the family who played the son-in-law, we love that actor. But he was actually in an episode in Season 1 where he was a head of a frat. In the lore of “South Side,” anytime you see somebody on screen, it’s the same person. We never use anybody as one character in this season and they’re a different character in another season.
Here’s the craziest part. Pat [Reidy], the guy who played his Jerry Scottadalehauser in Season 1, he ends up getting kidnapped at the end of Season 1. The woman who plays his wife is the same actress who’s sitting at the reception desk at the frosting place in Season 3 Episode 2, right? Then she shows up again in Season 3, Episode 3 with Jerry.
DR: Trying to buy a couch, of all things!
BS: We’re comic book nerds. It’s nice to have a little toy box where we can create our own lore. We’re really serious about comedy. And then we’re really serious about lore. We’ll make very small changes to a piece of set decorating if it’s not quite right and consistent with something we said three seasons ago.
Do you let yourself think about what the show would look like in future seasons? Or are the two of you primarily focused on what you’re working on in the present?
BS: I think we definitely want both shows to get another season, we would love to do more. One of my favorite things is when I run into somebody in Chicago or wherever and they say that “South Side” or “Sherman’s Showcase” got them through the pandemic. The idea that we have these shows that are bingeable and are fun, that people can watch and love, that’s really special. But I also think that Diallo and I really want to make sure that we can keep making comedy.
DR: I’ve been thinking a lot about Robert Townsend lately because I go back and I watch a lot of those things. Everybody remembers the cast of Saturday Night Live that they love so much. But I didn’t realize until recently just how much the comedy of Robert Townsend, and his “Partners in Crime” series when I was a kid, really informed my comedy. It’s not just “Hollywood Shuffle.” I clearly watched a lot of episodes of “Partners in Crime.” I feel like he’s like Nic Cage, one of these people who was great and appreciated by people at the time, but his name doesn’t get brought up enough.
BS: I’ll go further. I feel like Robert Townsend is definitely the unsung hero of Black comedy. You know, he’s definitely the guy who informed a lot of us. “Hollywood Shuffle,” by the way, is still way too damn relevant, sadly. Like he would think, “Oh, it’s an old movie. It doesn’t really have any relevance nowadays.” And then you watch it and you go, “Oh, crap. It’s so poignant.”
DR: I feel like you and I are so good at finding talent before maybe even the city of Hollywood knows who they are. When I watch any of those old things, I’m like, “Oh, there’s a 16-year-old Marlon Wayans talking to Robin Harris.” It’s not even just the stars alongside Robert Townsend. It’s all the people in between the pockets. 10 years from that time, you wouldn’t be able to afford to shoot this, because everybody’s price point went up. But at that time, he was working with so many funny comedians. I feel like that’s one thing that we’re really good at, is finding who might be big in the next three to five years.
New episodes of “South Side” Season 3 premiere Thursdays on HBO Max.
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