Putting Regular People on TV: A Q&A with ‘South Side’ Comedy Screenwriter Diallo Riddle

Diallo Riddle was one of the lead writers for the comedy sitcom South Side before it was canceled by HBO Max in February 2023. Riddle is a multi-talented creative who has since done work on the Daily Show during Marlon Wayans run, co-produced the podcast One Song with songwriter and musicologist Luxxury, and has made appearances since 2023 on various podcasts talking about music, creating and writing Emmy-nominated shows, and creating comedy. 

Riddle wrote a large chunk of the episodes of South Side and played the character of Alderman Gayle. He and Bashir Salahuddin, who played Officer Goodnight, have been writing jokes together since their days at Harvard University, where they started creating a medley of different works in the late 2000s. This includes Soul Train-esque Sherman’s Showcase, work on Late Night with Jimmy Fallon, Marlon, Brothers in Atlanta, and a long list of work they did together and separately. 

After the cancellation of South Side was announced, Riddle tweeted, “The show that never lost one fan…” and thanked the fans, cast, and crew.

As I was writing “Chicago Millennials Discuss How The City Has Been Depicted On Screen” for South Side Weekly, I had the opportunity to speak with Riddle about the show that my peers and I appreciated so much and what was his creative process like for creating the characters and characterizing the city.

This interview was edited for length and clarity.

Cordell Longstreath: When creating the character, what was your inspiration for Alderman Gayle? Was it based on working around politicians? 

Diallo Riddle: We did not have an alderman in Atlanta; we have a city councilman. We have a city councilman with the same role, but we don’t have wards. You know, we have zones… The thing about Gayle; he’s not a man of ideology. He sees opportunities that he goes for.

We had always gone into the show hoping to show people on the South Side at various levels of, I don’t want to say power, but to a certain extent, like varying degrees of status. In one of our favorite movies, Coming to America, you had some poor characters, some rich characters, some smart characters, and some dumb characters. And we always wanted to show that the South Side isn’t all one thing, either. 

There are some characters who make a good living, some who are just making it by, and others who actually have a little bit of political or social clout, and what do they do with that bit of clout that they have? So that was one thing we wanted to do. We wanted to show somebody in our show who may not have the brass ring of power, but is not powerless. Secondly, you can only talk about Chicago if you talk about Chicago politics. My character was an avenue to do that.

And when we started doing our work, I would hear the stories from the writers in the room because I’m one of the only people in that room who was not from Chicago. It was me and Michael Blieden, and we were the only interlopers. Everybody else was from Chicago. When you hear the stories about the politicians, specifically about the aldermen, you’re like, oh, this is crazy! You would just be like, how is this real? How does this person get away with it for so long? 

We also did independent research. Some of the stories about the things that various aldermen had been accused and convicted of were almost too crazy to make up. And we put that in the script. It was a little broad, you know, the whole thing about him inserting himself into the collection of parking meters payment so that he could amass a great wealth, that seems like something out of the 1980s Eddie Murphy, Dan Ackroyd [skit]. 

By the way, I feel South Side has been very good at predicting the future. So, for example, we did an episode called DJ Alderman, where he decides more than fixing potholes, which is the unglamorous side of what he does for a living, he’d rather be a DJ. And then I looked at him a couple of months later. In real life, there was an alderman going around his district DJing a fundraiser, so it’s just funny that sometimes we think we’re a pretty absurd comedy, but then life happens. You find out that God is more absurd than us.

Is there any politician you feel he is similar to?

It’s crazy, man. I think that that’s the kind of stuff that can come out in local politics. Once they get to a state and national level, they’re usually a little more polished. Nowadays, who knows, but he’s a local guy. And the fact that he lied about where he’s from is very George Santos. Nothing we did with Alderman Gayle was so broad and ridiculous that it couldn’t be believed. 

The episode on Simon and Kareem graduating from community college was very surreal. It reminded me of my experience of graduating here in Chicago.

That was our first episode. I think we set up the show [thinking] this will be a different kind of show. It’s not going to be, you know, people laughing at the privileged and the elite. I feel like there’s a lot of that out there right now, from Secession to White Lotus. Billions, there are so many shows like this, just like how rich even Game of Thrones is. This is how the rich and powerful live. And this is why we should throw stones at them. 

But we don’t spend enough time just sort of focusing on what’s the life of regular people. This is my background, you know, I didn’t come from… I grew up on the southwest side of Atlanta. I think my father probably topped off at about $38,000 a year, you know what I mean? Like, we lived good because that’s in Atlanta in the 80s, you [could] live on that, but it’s not like I had any clothes with a label on it. I had the same sweater every other day, do you know what I mean? Bashir’s family is the same way. I’m one of six. He’s one of eight. We come from real working-class backgrounds, and we wanted to do a show that reflected that because I feel like that’s what’s not on TV quite a bit. You know, it’s almost like TV thinks that it can only tell the story of the people who are winning, but here’s why they’re so sad or here’s why they’re so terrible. 

I wanted to tell a story about ambition, and those people who are basically trying to make it out of the hoods, but also not trying to leave with it. They want to make a better life for them and for their families. And sometimes we just don’t see much of that on TV. And it’s funny, like, that’s how more people live than not, but yet, it’s hard to get it across that development rubric. Sometimes it’s hard to tell network executives who are usually driving a premium luxury car, “Hey, here’s a story about real people.”

What role do you think comedy has in terms of humanizing our experience of life? What role do you think it has on people’s self-image in their perception of where they are from?

I’d say as much as I love those old Warner Brothers Bugs Bunny cartoons, that’s where we get a lot of, you know, most racist stereotypes. I mean, they’ve been cleansed. But I’m old enough to remember when there were episodes where a bomb would explode and Bugs Bunny’s face… Suddenly, he’s in blackface, and you start singing Manny. I mean, when you think about characters, like Slowpoke Rodriguez, you know, a Mexican mouse who is friends with Speedy Gonzales, but Slowpoke Rodriguez, he’s lazy.  the joke about that character. TV and film, whatever comes next, I don’t know if it’s streaming or just web-based video, whatever comes across on our phones—these are our reflections. We look at our phones, which are essentially black mirrors, and we see a reflection of ourselves. 

I think that the good news is that there are now more people of color who are creating their shows, not worrying about acting, but writing shows, directing shows, doing makeup on shows, roles with no visibility [because they’re behind the cameras], working behind the scenes on shows, all that leads to diversity. I know that people like to slam diversity, but the reason why we’re demanding diversity is that we are a voice that has not been at the table, we have not been able to define ourselves too often. And I think that that’s hopefully changing. 

I hope it doesn’t change and then go back to the way it was like in the 90s. I feel like we had a lot of Black TV shows. We had Martin, we had the whole WB for a little bit, and we had a whole network, UPN. They always came to us when they wanted to start their networks, but then, when those networks went away, we went through another period where there was just not a whole lot of color on TV. Then, thankfully, there was another generation that came along, and I am proud of that generation: Issa Rae, Donald Glover, Lena Waithe, and so many others. Right now there is a new generation of people who are creating a better, more accurate depiction. It’s not even that we’re trying to paint a rosy picture. It’s just a more accurate picture of our community. 

Thankfully, it’s not just Black men. I always say South Side wouldn’t exist as it does without the active input and driving force, quite frankly, of Black women, since we have more Black female writers on the show than Black male writers. I think that’s why our female characters ring. They are some of our most popular characters because you don’t have a roomful of non-Black women writing those characters. So I think the diversity is real; self-image is only helpful when you allow people to sort of, at the very least, control their own image. That doesn’t mean that, as a Black writer, you can’t write now. I’m here. But I think we’ve had so much experience over our lifetime with characters who aren’t Black that I think it’s easier for us to write them sometimes than it is for them to write us.

What was your goal for characterizing Chicago in your show?

We wanted it to be [like] Seinfeld. We didn’t want the show to be like, “Oh, by the way, that takes place in [Chicago].” No, we wanted it to be like they were there. They were name-checking Daley’s, they were name-checking Cottage Grove, you know, and going down to Daley’s, which we couldn’t use their name, so I think we had to call it Washington’s on the show.

Speak on the hustler spirit.

One thing we like about our show is that even though it’s set in Chicago, and the jokes are very Chicago-specific, people from Atlanta to Philly to LA to, you know, Montgomery, Alabama love the show because they see their own cities in our depiction of Chicago. So, yeah, I think to a certain extent, if you go to Atlanta, you will meet a barber who’s got a hot young rapper he’s trying to produce. And by the way, he can also tell you, he can sell you some spray paint, you know… So, yeah, that’s just the hustler spirit that thrives in communities where people want something better for themselves, they want something better for their children and their families.

How did your team respond when you were notified that South Side was canceled? Was it something that you expected?

It’s safe to say we were all disappointed. I personally felt our insanely large and talented ensemble cast could have gone the same distance as It’s Always Sunny In Philadelphia. But Bashir, Sultan and I also felt that we ended the third season of the show having never delivered a wack episode. We felt every single scene of every story we told could stand on its own, and we were proud of that.

So nowadays, we’re focused on delivering more shows like South Side, and whether these new shows are huge hits or not, we are having a great time over here, because we simply enjoy creating comedy, telling stories, and breathing life into characters we love.

Cordell Longstreath is an Army veteran, writer, community advocate and activist, and teacher. He last wrote about how Chicago has been depicted on screen.