Diallo Riddle makes ‘South Side’ both funny and real

In the first episode of South Side, Comedy Central’s all-too-funny, all-too-real series set in Chicago’s Englewood neighborhood, the show’s humanizing message is made clear from the start. “Sad news from the city’s South Side, where yet another senseless act of violence has authorities baffled,” says an anchor on the fictional local 22 News show. But when she hands off to a white television reporter talking to residents at the scene of a tragic shooting, the story takes a left turn. Rather than wallow in the bleakness of it all, best friends Simon (Sultan Salahuddin) and Kareme (Kareme Young) are busy celebrating their graduation from Kennedy-King College. “We did it!” Simon proclaims, taking over the broadcast, degree proudly in hand. “Business administration, ya dig? Got that piece of paper, ya dig?”

Chicago has seen too many deaths and too many funerals. But there is always hope. There’s always laughter. “That was absolutely intentional,” says Diallo Riddle, who co-created South Side with friend and writing partner Bashir Salahuddin (Sultan’s younger brother). “We wanted to start the episode with the news because the news can paint a certain picture of the city. There is a negative way that Chicago is portrayed too often, not only by the media but by politicians. When you meet people from Chicago they are not ashamed of it. They know that they have some challenges, but they love their city.”

Indeed, the characters on South Side are never dragged down by lazy, one-dimensional tropes. Lovable knuckleheads Simon and Kareme are seemingly stuck in dead-end jobs at a rent-to-own store, but they show plenty of heart and ambition, albeit with often comical, harebrained results. The pair’s boss at Rent-T-Own, Q (Quincy Young) delivers deadpan one-liners with ease. There’s tightly wound Officer Goodnight (Bashir) and his delightfully shady partner Sgt. Turner (played by Salahuddin’s real-life wife, Chandra Russell). Riddle himself shows up as above-it-all, cynical lawyer Allen Gayle. “But I’m the only one on the show who is not from Chicago,” the Atlanta native jokes.

Riddle’s pen game is stout. After graduating from Harvard University, he took on various projects with Bashir Salahuddin, eventually writing for Late Night With Jimmy Fallon, which earned them Emmy nominations. Riddle co-starred on the short-lived NBC sitcom Marlon and has writing credits on The Last O.G. and The Maya Rudolph Show. His most oddball project may be IFC’s Sherman’s Showcase, a musical sketch comedy (conceived with Salahuddin) that’s part Soul Train, part Documentary Now! and part In Living Color.

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This interview has been edited for length and clarity.

Who came up with the idea to make the appliance and furniture store a primary part of the show?

It was pulled from real life. Q, who manages RTO on our show, used to work for Rent-A-Center for years, and while working at Rent-A-Center he would always tell me these really messed-up stories about people not being able to make the payment on their couch. They would go to the house and try to take the couch away and the person would be like, ‘I’m not getting off this couch.’ They ended up carrying out the couch with the dude sitting on it.

But as funny as that is, let’s not sleep on the fact that a lot of those rent-to-own businesses are basically a predatory lending scheme. There’s a lot that goes into our show, from highlighting the city’s entrepreneurialism to just trying to get people to be smart. My mom was a social activist and a painter. Bashir and I want to inspire people to make wise decisions while we make them laugh.

What would you say is the most Chicago thing about South Side?

Just the fact that we can have a whole conversation not only about Harold’s [Chicken] but also about the mild sauce. I also have to give a shoutout to Nefetari Spencer. There’s a scene where her character, Keisha, who is at her first day at Rent-T-O, makes a speech and apologizes for going to Kenwood Academy (laughs). You have to be from Chicago to even understand what that means.

How important was it to hire Chicago-based actors and writers?

I mean, my writing partner [Bashir] is from Chicago. All of the other writers on the show, all the series regulars on the show … everybody is from Chicago except me. We went out of our way to cast almost all actors from Chicago. We hired writers from the South Side, even if it was their first writing credit. But there is one writer from the North Side who always gets s—.

I’m a Cubs fan who grew up on the South Side, so I know.

So you get it! Kareme, who is known as K on the show, is a South Sider who is also a Cubs fan. People on the show are like, ‘How could that even be possible?’

There’s a lot happening on South Side. I see traces of Friday, Seinfeld and the goofy, over-the-top essence of The Simpsons.

You named three of our favorite things. We love Friday and The Simpsons. We didn’t know what a marble rye was, but we still loved Seinfeld. It’s a little bit how we see our characters chasing after those Jordans in episode four. We always go out of our way to make South Side very specific to Chicago. But you still will get the joke even if you aren’t from Chicago, the same way that you don’t have to be white and living in New York to appreciate Seinfeld.

You met Bashir in college. Who was funnier?

Ha! That was the wonderful thing. We were never competing to be the same kind of funny. Our energies are completely different. We’ve been friends for 20 years now. Bashir and I originally met as part of an a cappella group. We would go to any coffee shop that would allow five black guys in matching sweaters to sing.

Do you still have those sweaters?

Ha! And our whole purpose was to [be in the same lane] as Jodeci, Shai, Silk and all of those R&B groups! That was our goal.

So what’s your go-to ’90s-era R&B album?

My personal favorite was Tony! Toni! Toné!’s House of Music. That’s a masterpiece that did not blow up like their other albums. For me, House of Music ushered in the era of neo soul. People slept on that album.

Let’s get into Sherman’s Showcase. There’s one skit called “Now That’s What I Call White Music,” which is a spoof commercial for a collection of songs from white artists who made records that “Black people f— with,” like Queen’s “Another One Bites the Dust” and Hall & Oates’ “I Can’t Go for That.” What’s your ultimate white “black” song?

I always start with Bobby Caldwell’s “What You Won’t Do for Love.” There are still black folks every day discovering that he’s white. By the way, this is exactly how we came up with Sherman’s Showcase. Bashir, myself and Questlove were having a conversation about music. We were having a funny discussion about all the songs Rihanna said no to first (laughs).

Absolutely! Bashir and I have been writing songs going all the way back to college. We wanted to write the music for all of Sherman’s Showcase because it’s a fictional show and there are going to be live performances. We immediately got with John Legend because we wanted every single song to be great. And John was like, ‘I can help with that.’ We also got the chance to work with Ne-Yo and Phonte (formerly of Little Brother).

Those are some serious songwriting credits.

I have to say this series has been great because it has sort of given us our own TV studio and our own recording studio. Those fake movie trailers on Sherman’s Showcase? We kind of want to make those into actual movies. I get to work with all my favorite musicians and comedians. We were shooting on the Sherman’s Showcase set and I posted on social media, and I got a text from Lil Rel [Howery] and he’s like, ‘Yo … y’all shooting right next my neighborhood. Can I come on down?’ We wrote something for him on the spot. I think it’s one of the funniest things we have ever done.