Expanding the universe of South Side

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. South Side was refreshingly different from other dramas that focus on the violence and real disadvantages south-siders face. It demonstrated that while there may be doom, one thing Black people know is how to laugh through the pain. It also captured the essence of how our communities cultivate joy in everyday life.

Bashir Salahuddin from Chicago and Diallo Ried, who hails from Atlanta, created the show. It was highly praised by viewers and was renewed for a second season with ten episodes. The show’s writers’ room was working on season two when the pandemic hit, which unfortunately halted the process and led to major rewrites. South Side has many stories to tell and season 2 features local actors, celebrities, and more well-known Chicago names. 

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 2 premieres on HBO Max streaming service November 11. 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.

JanayaGreene: The theme song for South SideIt’s undoubtedly one of the best parts about the show. It’s one of my favorite things about it. How did you create it?

Diallo Riddle:It was Chandra I believe. [Russell]Sergeant Turner plays Sergeant Turner and really enjoyed a song by Chicago musician Sasha Go Hard. So we reached out to her and were successful in getting her. We asked her how likely it was that she would write a theme song for our show. We were thrilled when she applied. We received two songs from her, but only one. [the words] “south side”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.

That is what I love to hear. 

We are grateful that she was kind enough to sign the cosign for us. I think it’s the most fire theme song since Family Ties.

I agree. You’ve created several shows, including Sherman’s ShowcaseAnd South Side. Did you notice any overlap in the development of these?

The process is very different. Even the things that lead to the ideas are different. South Side is merely drawing from the most funny things that have ever happened to people in real-life, but in a more grounded way. 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. It did get me thinking. “Well, here’s one potential solution that would never happen, because it’s absurd.”I felt 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 here. 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 was born as a show because Bashir would return home to Chicago and hear stories from his childhood friends about the wild things they did, including his friend. [actor Quincy Young]He plays Q on the series. Q was actually a Rent-A-Center employee and would talk about the crazy things they would do, when they would do them. “replevin’,”This is basically repossession. Again, that’s sort of a bad dark place, but the stories themselves are really, really funny. Sometimes the most unexpected places can provide the best comedy. That was what we were like when we were. “This is gonna be a show,”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. We were drawing directly from a life where someone found humor in tragedy. That is what inspired us into creating 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 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. Bashir was astonished that I shared all these wild stories about Atlanta growing up. The show was developed at HBO for four years and never aired. This was a very difficult time in my professional life, but we never gave-up on that 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 was born in the 80s. Kennedy-King [College]He was in his back yard . .  We grew up in very similar circumstances. It’s not the straight-up hood, but it’s also not the area that most working Black families aspire to either. We got to see both sides.

His stories as a child were very similar to mine, and we both admittedly had borrowed some stories from my time living in Atlanta. We have season two about the number one party organizer in Chicago. Something happens to this guy. We had discussed doing an episode about the idea that the number 1 party promoter in a Black city or neighborhood is like a very important head state. He or she is the one who puts up the advertisements on the radio station 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. It was also incorporated with some of Bashir’s wild Chicago stories. 

For example, and I don’t think this gives anything away, he once showed me a flyer for a crazy funeral. First, I thought it was insane that a flyer for funerals existed. There was a flyer advertising a Chicago funeral. 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. We decided to just try it a little bit. It’s really hard to beat real life. 

Our people are very creative, truth to tell. It was hard to believe that this person would actually have a homecoming. South Side is, in some ways, a love letter for Black communities everywhere. We draw from our experiences living in Black communities. All of those experiences help to make the show.

South Side season two is now available HBO Max streaming.

You’ve said everybody in the writers’ room for South Sideis 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. All but one of the Chicagoans are from the south side. One of them is from north side. He’s a very funny writer. Bashir and me both come from large Black families. He’s one of eight, I’m one of six. That feeling you get when you are with a Black family on Thanksgiving or any other 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? We draw on the experiences of our mothers, fathers, uncles, aunts, and sisters, as well as our brothers. 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 fastest way to get rid of 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. Are there any Chicago writers?

There were certainly people. [working]Chicago during the pandemic. Production has been reestablished here and people are back out there, 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. We were close to finishing this season when the pandemic struck in 2020. Everything was just kinda shut down. We were just sitting around. We realized that we might be able to shoot in 2021. So we brought the room back together using Zoom. It 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. 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. 

Along with creating new material on set we also had to rewrite 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 people in so we were very careful with the camera movements. It will make anyone who watches it feel like they have a South Side season. They won’t feel like: “Oh, there’s that weird season where they only have like two characters in each scene.”Some things will look much more packed with modern technology than they used to, I believe.

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 which takes place inside an auditorium and a scene which takes place inside 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. It was difficult to shoot it, especially because we didn’t know how long. We wanted to give South Side viewers at least one more season. We’ll see later on if we have to do anything about that. We do want people to find the show 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 2?

We started filming in mid April and finished it at the beginning or middle 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, mostly from the south side of the city, are moving to the suburbs because they can afford it and there are more opportunities. 

In some ways it’s a heavenly place, right? It was something I noticed a lot as I was leaving Atlanta to go to college. All these people from LA were moving to Atlanta. They were all alike in the 90s. “LA is expensive.” It’s really wild. Atlanta is loved by its Black mayor and 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. 

You feel like you’re in a group of people when you get off the plane at Hartsfield-Jackson Atlanta International Airport. “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 find the Atlanta that suits your needs by going there. You can find The Real Housewives of Atlanta or the Donald Glover-designed Atlanta. There are many places you can visit to find Black neighborhoods, new Black communities, and wealthy Black neighborhoods. You can find the right hood and all parts of Atlanta. 

Atlanta can be found that does not tolerate Black people. . . 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. Atlanta just has that appeal to me. 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 in Atlanta and Chicago?

There are many. People who grew up in New York’s projects didn’t understand why certain areas 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. Atlanta has its Dan Ryan Woods. 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 long to live in. 

A vibrant hip-hop scene. Drill music is different from trap music. The violence is real. But, I think South Side, or any show we eventually do, in Atlanta, South Central LA, Philadelphia or whatever, tries to de-emphasize violence because I feel there are enough places in the media to find it 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 as such. 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 SideDo you think that moving to HBO Max will have an impact on who is watching it? 

I think it’s a great home. I believe streaming is a better platform for our show. No diss to Comedy Central because they’re the ones who originally said yes to the show. I received so many more DMs. e-mails. and texts from people who had never seen South Side before. These are the people who I believed would have seen it 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 at their own time. They watch it in bed at three in the morning while their spouses sleep. This is how to get people to view. When Comedy Central called me and said, “It was nothing but good news!” I was so happy. “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 HBO Max has its own brand. And I’ve been watching everything on it right now.

The official trailer to season two South Side.

Was there anything you wanted to do with season two? 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 believe that season two was necessary to expand the universe of South Side. South Side can be compared to Springfield on The Simpsons or Westeros in Game of Thrones. All we wanted was to 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. We also learn more about some of their characters. 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 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 best things about the show, aside from the fact that there are almost 200 speaking parts in season 2, is the fact that they have so many. 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 would also like to mention that nearly 100 percent of our casting was done 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 upload a photo at 95th and Ashland. This is where I grew-up. Is there any place we can expect to see this year?

There, we shot a scene together with Chance the Rapper. We’re excited to grow. We were at Ashland and 95th. We were done. We finally got to shoot—I still want to call it Comiskey—at Guaranteed Rate field. We were able to shoot in the Shedd Aquarium. We shot all around 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.

What is it like to be at a White Sox Game?

Actually, they allowed me, Bashir, and Sultan, his brother who plays Simon. Simon was allowed to take it because he wanted to play baseball as an adult. He was allowed to throw it, but I was there to take the ball.

That’s cool. Chance was mentioned. You mentioned Chance.

Chance the Rapper was actually a friend of ours, Lil Rel. He 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. Chance brought his whole comedic act to the show and it was great. 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, and we got Money Maha from Power 92 92.3FM. She is a force of nature, and she does great things. Tone Kapone, WGCI 107.5FM, was our man. We’ve got Dreezy. She was amazing. 

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?

This is actually what Chicago shares with Atlanta. I love the radio stations. Because in LA and New York, it’s the same artists all day, and you can’t get any new music on the radio. Chicago radio stations, with their love for Lil Durk, as well as all the people who are coming to Chicago, were actually really enjoying it. I felt like all that music was on my way to work and back home. It was like I was there. “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 new music and I enjoy Chicago radio just as much as Atlanta radio. Atlanta had five hip-hop stations at one time. How can you stand apart? You need to try new things. I was able to find my station in Chicago, 92.3. I still check the playlist for 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 going to ask about your DJing.

I’m a huge house fan. Deon Cole and I DJed at Soho House on Saturday, which was all house music, while I was in Chicago. 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. The song is probably from 2015 or something similar. Everyone knew every word. The room burst into life.

The discography. Chicagoans will be able to identify every Chief Keef song.

They were screaming it like their lives depended on. It was all I could do. I felt 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 I ever heard of billiards. “Bricks”Gucci Mane. Atlanta knew every word right from the moment that the track began. It was insane. It was crazy, but it is what I love. It’s great when I get musically confused; it’s great when everyone is on the same page. 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. Music isn’t dead. That’s how I know it best. People still listen to their music and react to it. My favorite thing about hip-hop is Chicago.

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