Diallo Riddle, cocreator of South Side Credit: Kevin Scanlon

It’s been over two years since South Side debuted on Comedy Central and made many Black Chicagoans from the city laugh in a way that felt personal. Amongst the many dramas centering the violence and real disadvantages many south-siders face on television, South Side screened with a refreshing perspective that many folks from the south and west sides could appreciate. It reflected the reality that even though there can be doom and gloom, one thing Black people know how to do is laugh through the pain; it captured the essence of how our neighborhoods also cultivate joy in the everyday.

Created by Chicago native Bashir Salahuddin and Diallo Riddle, who is from Atlanta, the show was highly praised by audiences and was renewed for a ten-episode second season the month after the first episode aired in 2019. The show’s writers’ room was working on season two when the pandemic hit, which unfortunately halted the process and led to major rewrites. Fortunately, South Side still has more stories to tell than ever and season two includes local actors, local celebrities, and more well-known names from Chicago. 

This go-round we’ll see friends Simon and Kareme get into even more (fun) trouble at Englewood’s fictional Rent-T-Own (a riff on the insidious Rent-A-Center chain), and other spots on the south side. Season two premieres November 11 on the HBO Max streaming service. The Reader recently caught up with cocreator and co-showrunner Diallo Riddle to discuss what new places and people viewers can expect to see this season, how writing and filming during the pandemic impacted the show, and why Chicago’s Black communities are so relatable to people everywhere.

Janaya Greene: I would say the theme song for South Side is arguably one of the best things about the show. It’s one of my favorite things about it. What was the process in creating it?

Diallo Riddle: I think it was actually Chandra [Russell], who plays Sergeant Turner, who really liked a song by Chicago artist Sasha Go Hard. So we reached out and were able to get her. We asked her what was the likelihood that we could get a theme song from her on our show. She applied and we were really happy about that. She actually sent us two songs, but only one had [the words] “south side” in it. It’s a theme song and I was like, you know, if you have a song that’s tied with the name of the show in the song, that’s the one you gotta go with.

I love to hear that. 

She was nice enough to give us the cosign, so we appreciate it. I think it’s the most fire theme song since Family Ties.

I agree. You’ve created several shows, including Sherman’s Showcase and South Side. Did you feel any overlap in the process of developing these?

The process is really different. And even the things that give birth to the ideas are very different. With South Side, we are really just pulling from some of the funniest things that have happened to people in real life, in a more grounded sense. And I feel like Sherman’s Showcase is really our chance to invent wildly, wholly new things that have almost nothing to do with the real world. Just this morning, I was listening to the news, without going into too much detail, it was about something that’s very sad and dark. But it did get me thinking, “Well, here’s one potential solution that would never happen, because it’s absurd.” And I was immediately like, “Oh, this is a Sherman’s Showcase idea.” 

Whereas with South Side, because it is grounded, you’re really pulling more from your personal experiences. I grew up in Atlanta. My writing partner Bashir grew up in Chicago and all of our writers grew up in Chicago, but really, at the end of the day, whether you’re from, you know, southwest Atlanta, south side Chicago, South Central LA, or West Philadelphia, no matter which of these black neighborhoods you grew up in there’s similar experiences that we all have. So a lot of times we’ll set up a writers’ room with everybody just bringing ideas to the characters, but also talk about their personal experiences, what’s the stuff that happened to them, that was wild and crazy.

South Side came about as a show, because Bashir would go home to Chicago, and he would hear stories from his childhood friends about some of the wild stuff that they got into, including his friend [actor Quincy Young] who now plays Q on the show. Q actually worked at Rent-A-Center and he would talk about the crazy things that would happen, when they would do “replevin’,” which is essentially repossession. Again, that’s sort of a bad dark place, but the stories themselves are really, really funny. Some of the best comedy can actually come from the most unexpected places. So that was when we were like, “This is gonna be a show,” and we pitched it to Comedy Central. They’ve had so many people pitch them workplace comedies, but they’ve never had somebody pitch them a show based around a Rent-A-Center type of place. Honestly I feel like most writers, especially those in Hollywood, they don’t have these sort of life experiences. So we were pulling directly from a life experience where somebody found some humor in the tragedy. That is what led us to do the show.

Speaking of Bashir, what would you say are some of the most memorable things that you’ve learned about Chicago from him directly? As your creative partner, and also friend?

I’ve known Bashir since 1994. We met at Harvard and there’s honestly not any stories that I haven’t heard at this point, but it’s hard to pull one or two from any of them. I mean, he’s heard my experiences growing up in southwest Atlanta, which ironically, that’s why our first show that we ever pitched and sold to anybody was a show (that eventually went by the name Brothers in Atlanta). This is before Donald Glover’s Atlanta. I told Bashir all these crazy wild stories about growing up in Atlanta, we developed that at HBO for four years, and it never made it to air. So that was a really hard time in my career, but we never gave up on that kind of idea. 

With four years of working on the show about Atlanta under our belt, we decided to say well, let’s do a show about Chicago. So then we just started writing episodes that were based in Chicago about Bashir’s life experiences. He went to Whitney Young High School. He grew up in the 80s. Kennedy-King [College] was in his backyard . . .  we grew up in very similar environments. It’s not the straight-up hood, but it’s also not the area that most working Black families aspire to either. So we got to see both sides of it.

His stories growing up were a lot like my stories, and we admittedly had taken some stories from my time in Atlanta. In season two, we have this whole thing about the number one party promoter in Chicago and something happens to this dude. We had been talking about doing an episode based around the idea that the number one party promoter in a Black neighborhood or city is like, a very important head of state. He or she is the person with the ads on the radio station late at night . . . so, going back to our Atlanta pilot days, we’d wanted to do something like that that we’ve actually sort of outlined; something that we never got to do until now. Now that we’re on HBO Max we finally got to do that storyline. What was crazy was that it also blended in with some of the wild Chicago stories Bashir had. 

For example, and I don’t think this gives anything away, he once showed me a flyer for a crazy funeral. First off, I was like, a flyer for a funeral is insane. There was a flyer for a funeral for somebody in Chicago. Even though it’s sad that somebody died, the flyer itself is pure comedy. Some person has decided at some point that they wanted this for this person’s homecoming. It was insane. So we decided that we would just take it up just a little bit. It’s really hard to beat real life. 

You know, truth be told, our people are very creative. It was hard to top, in our story, what this person was actually going to have at their homecoming. I think that in some ways South Side is a love letter to Black communities everywhere, because we pull from our experiences in living in Black communities. We pull from all those experiences to make the show.

South Side season two is available to stream on HBO Max.

You’ve said everybody in the writers’ room for South Side is from Chicago or grew up in Chicago. What does the writers’ room look like?

Me, and one other writer who grew up in Detroit—we’re the only people who didn’t grow up directly in Chicago. Of the Chicago people, all of them but one is from the south side. One of them is from the north side. He’s a very funny writer. Bashir and I both came from large Black families. He’s one of eight, I’m one of six. You know, that feeling that you get when you sit around a Black family come Thanksgiving, or, really, every night of the week? When everybody’s trying to be the funniest person and everybody’s got jokes? That’s what we tried to duplicate when we put together our writers’ room. 

We have two white writers there, but it’s primarily Black folks sitting around, making each other laugh, talking about the strange, the wonderful, the hilarious. That’s really what we’ve been able to accomplish with both South Side and Sherman’s Showcase. Sherman’s Showcase is basically like Soul Train if you could go back and watch them now but with original music, what would that be like? Pulling on the experiences of our fathers, our mothers, uncles and aunts, sisters and brothers and all that. A few of us have got kids now so we’re even watching what they’re into. I think for both shows it’s very important that we maintain a sort of a contemporary point of view. We’re not trying to do retro humor, we’re not here to do any humor that’s been done before. The quickest way to shoot down something is to be like, “Oh, that would be how a 1980s sitcom would handle it.” We don’t ever want to do something tired. 

Speaking of the contemporary point of view, I’m wondering: with the pandemic, some writers’ rooms went virtual. For the new season, are there any writers currently living in Chicago?

There were definitely people [working] in Chicago during the pandemic. Because production kicked back up out here, people are back out here, people are working. Since there’s so much production right now, it would be hard to pull together the room that we pulled together for season two, right now. I’m glad that we got it done when we got it done. When we were writing this season, we were almost done, then the pandemic hit in 2020. And so everything just kind of got shut down, we were just sitting around. And then when we figured out that we would probably be able to shoot in 2021, we got the room back together on Zoom, which was not great. 

There’s a very different vibe on Zoom than when you’re actually physically in a room with a person. [The experience] was instructive enough that when we were writing season two of Sherman’s Showcase after that, we actually set up in a parking lot with a tent over it, and everybody was mad spaced out. It’s just not fun to try and do a writers’ room on Zoom. I think that we learned that lesson. 

But the other cool thing about South Side is that once we were actually shooting in Chicago this spring, just to see people, you know, just to be in the same presence of them even if you’re wearing a mask, it felt different. And we were able to come up with some jokes while we’re shooting on set that I think we would have not come up with if we just continued to maintain everything on Zoom. 

In addition to coming up with new material on set, we had to do some significant rewriting on some of the existing scripts. We had a whole scene that took place at the Bud Billiken parade  but we didn’t want to do anything where it was obvious, “Oh they must’ve shot this season in COVID.” We like to bring the community in and so we got very tricky with the camera movements in scenes. I think that anybody watching it will feel like they got a season of South Side. They won’t feel like: “Oh, there’s that weird season where they only have like two characters in each scene.” Through the use of modern technology, some things will look a lot more packed I think than maybe they were.

So the Bud Billiken scene, that’s still happening? It’s just looking different than what you planned?

No, that’s going to have to wait until season three. We have a scene that takes place in an auditorium, we have a scene that takes place in a convention center. I actually pop up as an actor in the season five premiere of Insecure and what was cool about that was I got to observe firsthand how people are able to panel the image of a crowd so that it looks like a lot of people are there when they’re not. We made the decision early on with South Side that we didn’t want to do anything related to the pandemic. We thought it’s just a bummer of a subject and we didn’t want to do something that was going to remind people. Especially when we were shooting it because we had no idea how long it was going to go on. We wanted to give people at least one more season of South Side as they know it. We’ll see later on if we have to do anything about that. At the end of the day we do want a show that people will find entertaining. It’ll be interesting as TV creators whether we’ll start incorporating that more into shows as masks and all the other stuff becomes more a function of daily life.

How long did you film season two?

We started filming mid-April and I think we finished at the top of July.

You’re from Atlanta and I don’t know if you know, but I feel like now Atlanta is kind of being considered Black Chicago 2.0 because so many Chicagoans are moving to Atlanta. Black Chicagoans, a lot from the south side, are leaving in general for the suburbs due to affordability, and other places for more opportunity. 

In some ways it’s a heavenly place, right? I noticed that a lot when I was leaving Atlanta, going to college, all these people from LA were moving to Atlanta. At that time in the 90s they were all like, “LA is expensive.” It’s really wild. People like Atlanta because of its Black mayor, Black police chief. There’s a whole group of my friends from high school who call Atlanta “Wakanda.” The city is expanding so quickly and so fast that every time I go back, where there were trees, now there’ll be a grocery store. It’s expanding fast so there’s a part of me that wishes that Atlanta was a little more cool and calm, but I get it if you want to go to a city with a huge pool of single young Black people, everybody kind of having fun. 

Once you step off the plane at Hartsfield-Jackson Atlanta International Airport, you sort of have this vibe of like, “Whoa, there’s a ton of Black people here.” That’s just the thing that Atlanta has going for it that a lot of other places don’t. You can go there and find an Atlanta that suits you. You can go there and find The Real Housewives of Atlanta, the Donald Glover artistic Atlanta. You can go there and find old Black neighborhoods, new Black neighborhoods, wealthy Black neighborhoods. You can definitely find the hood, and you can find all parts of Atlanta that suits you. 

You can find an Atlanta that avoids Black people entirely . . . you know, areas of pockets inside and outside of the city that you know, there’s not a lot of Black people. I don’t know why you’d be doing that. But that’s an option as well. I just find that Atlanta has that appeal. There’s a lot of money to be made there, a lot of jobs, the houses are cheap—I get the appeal.

Do you see any similarities between Atlanta and Chicago?

So many. I know people who grew up in the projects in New York never understood how some places have trees in the hood. That’s one thing. When you’re flying to Chicago or Atlanta, one thing that immediately jumps out more than in New York, LA, Philly, or even Detroit, is just the sheer number of trees. We have our own version of the Dan Ryan Woods in Atlanta. You can just go and be in nature and they’re right there in the city. 

I didn’t know it at the time that we became friends in college, but me and Bashir grew up in very similar environments. We don’t have Hyde Park [in Atlanta], but we have Misty Lake: a neighborhood Black people aspire to live in. 

A thriving hip-hop scene. Drill music versus trap music. Sadly, the violence is there, but I think one cool thing about South Side or any show we eventually do in Atlanta, or South Central LA, or Philadelphia, or what have you, we try to de-emphasize the violence because I feel like there are enough other places in the media to find that getting emphasized. We try to emphasize the human stories, because there’s people who grew up in these neighborhoods. You know, I didn’t wake up every day thinking like “Oh, shit, imma die,” like no, not like that. I think it’s important to point out to people who only see the bad news reported to them to know that there’s still plenty of people living their whole lives down there.

With South Side moving to HBO Max, do you think it will impact who is watching? 

I think it’s a great home. I think streaming is a much better platform for our show. No diss to Comedy Central because they’re the ones who originally said yes to the show. Even just when season one of South Side went to HBO Max, I got so many more DMs, e-mails, texts, from people who you could tell were seeing it for the first time. These are actually people who I thought would probably watch it when it was on Comedy Central. 

It’s hard to tell people in 2021 that you want them to watch this show at 9 PM. That’s a really old school way. Anytime I have to post anything for Sherman’s Showcase, I say, 10 PM Eastern 9 PM Central and I’m like, what year is it? People watch things on their own time and they watch it at 3 in the morning in bed while their spouses are asleep. This is the way that you have to get people to watch. So I thought it was nothing but good news when Comedy Central called and said, “Hey, you guys are basically an HBO Max show now.” We were like, that’s great, because I would say Netflix and HBO Max are the coolest streaming services. No diss to Hulu or Amazon but I don’t really know what their brands are. I know that HBO Max has a brand. And I’ve been watching everything on it right now.

The official trailer for season two of <i>South Side</i>.

Was there anything that you wanted to accomplish with season two of South Side that you weren’t able to communicate in season one?

No, it wasn’t a matter of not being able to communicate anything in season one. I think for our purposes, we wanted to expand the universe of South Side in season two. So if you think of South Side as Westeros in Game of Thrones, or Springfield on The Simpsons, all we wanted to do is say, OK, you met those characters. Now let’s meet more people who live on the south side. So we get to see more of who Officer Turner is, we get to see more who the character Kareme is, and in finding out more about these characters, you find out more about the people that they know and meet in the city and I think that’s really positive. If anything, we’re just trying to expand the universe. 

Here’s a fun fact: the pandemic actually had the unintended coincidence of having us return to a lot of the actors we had in season one who we just loved. And we find out more about some of their characters too. So for example there’s a dude who is a pizza delivery guy in season one, we find out, he had like three or four more jobs that we just didn’t even know about in season two. And that’s because in the pandemic, you couldn’t really do auditions in person. This is a little bit sad for all the wonderful actors who we haven’t had on the show yet and we’ll fix that in season three, because I think by the time we’re shooting season three, we should probably be able to audition in person again. But because we couldn’t audition in person and auditioning over Zoom is weird, we went back to some of the actors, even if they didn’t have a big part, who we knew had delivered funny lines the first season. We went back to those actors and actresses and were like, “Yo, this time you’re gonna play this person, you’re gonna play this.” So you’ll see a lot of familiar faces from completely different contexts. I feel like what’s cool about that is it builds out those characters and makes you say, “Oh, that’s just another character on the show.”

One of the things I love most about the show is that we have almost 200 speaking roles in season two. Some of those roles might only be like a couple of lines, but they’re really funny lines delivered by really funny Chicago-based actors. I also want to point out that we went out of our way to do almost 100 percent of our casting out of Chicago. I can’t think of anybody we flew in for season two. There have been some really good actors, by the way, who auditioned for both seasons and for whatever reason, they haven’t been chosen yet, but I’m still thinking about parts for them in season three, if we get a season three, because I think they’re really funny and Chicago’s just got a lot of really good actors.

We’ve seen a lot of the characters all over Chicago in the show. I saw you post a photo on 95th and Ashland, where I grew up. Are there any notable places we can expect to see this season?

We shot a scene with Chance the Rapper there. We’re excited to grow. We were on 95th and Ashland. We were all over. We finally got to shoot—I still want to call it Comiskey—at Guaranteed Rate field. We got to shoot in the Shedd Aquarium. We were shooting all over the city. There’s one Chicago reference that I’m not going to give away that we’re happy that we were able to work in. 

They allowed me to shoot the first pitch of the game so it’s definitely a second home to me now.

At a White Sox game?

Yeah, actually they allowed me, Bashir, and his brother Sultan, who plays Simon, and we gave it to Simon because he actually really wanted to play baseball as a kid. We allowed him to physically throw it, but I was on the mound.

That’s cool. You mentioned Chance. Can you mention any other potential notable people who may be in this season?

We got Chance the Rapper because he actually texted a mutual friend, Lil Rel, and was like, “Yo, I really want to drop in on South Side.” We actually offered Chance another part but he read that script and he was like yo, please let me be this character and I gotta say I can’t imagine that character that he chose to be being anybody else. I think Chance brought his complete comedic actor A-game and it was so funny. We had to actually edit down the stuff he was saying to fit the time of the show, but you’re going to see Chance being hilarious. Lil Rel is back and you’re going to find out what’s happened to his character Bishop in the time in between seasons. We got Vic Mensa, we got Money Maha from Power 92 92.3 FM. She comes through, does something. We got my man Tone Kapone from WGCI 107.5 FM who comes through. We’ve got Dreezy. She was great. 

Oh, [the comedian] Deon Cole, you know, one of Chicago’s finest, pops onto an episode. The thing that’s lovely about South Side is that we never feel like we need a famous face for an episode but if a famous person reaches out, and is like, “I’m a huge fan of this show, could I please come on and do something?” then we’ll play ball and it never takes away from our main character. 

Are there any Chicago-based musicians that you’re enjoying right now?

Actually this is one of the things that Chicago has in common with Atlanta. I love the radio stations out there. Because in LA and New York, it’s the same artists all day, and you can’t get any new music on the radio. But Chicago radio stations with their love of Lil Durk, and all the people who are coming up there, I was actually really enjoying it because I feel like all that music I was ingesting, it was just like on my drive into work and my drive out of work. Like I was just like, “I wish LA radio could get this.” It’s not like LA doesn’t have local artists. I just love feeling like I’m the first cat on some new stuff. I like to hear the fresh hot new stuff and so I appreciate Chicago radio in the same way I appreciate Atlanta radio. Atlanta at one point had like five hip-hop stations. How do you stand out? You gotta play some new stuff. In Chicago I found my station, it was 92.3, and I was comfortable with it. I still actually check the playlist because I need new music.

It’s weird because as a house music fan and as a fan of electronic music, you wouldn’t think. I’ve actually DJed for a station there.

I was gonna ask you about your DJing.

I’m a huge house fan. In fact, when I was in Chicago, me and Deon Cole DJed one Saturday at Soho House, all house music. I did a couple of nights at a place called Arbella and you know like there were a couple of DJs in town I liked; shout-out to my man Quicktastic, he’s a great DJ. But what I would say about when I was out there is that I don’t find that I’m like listening to any of the college house music shows. I’m really just listening to what’s hot on the streets because there’s just something vibrant coming out of the music of Chicago right now and you know that’s what I was really getting into. We threw a rap party, by the way, and I was playing all the hot new stuff and then somebody came over and requested a Chief Keef song I’ve never heard; I’ve never heard this song in my entire life and I listen to a lot of Chief Keef, especially when he was like all over everybody’s radio. I think the song is from 2015 or somewhere around there. The room exploded, like everybody knew every single word.

The discography. Chicagoans will know every Chief Keef song.

They were yelling it like their life depended on it. I was with it. I was like, “This is exactly what I love.” I’ll never forget the first time I went back home to Atlanta from college and the very first time I was at a billiard hall. First time that I ever heard “Bricks” by Gucci Mane. Everybody in Atlanta knew every word from the second that track started. It was crazy. But I love it. I love it when I get musically stumped; when everybody is on something. It’s not on the radio, but everybody’s already loving it and knows every word, you know what I’m saying. To me that’s like the greatest. The best way that I know music is not dead. People are still getting their music and still reacting to it. The hip-hop in Chicago is my favorite thing.