The key to a successful comedic partnership? It’s more simple than you might think.
“We make each other laugh,” Diallo Riddle tells LA Confidential of his relationship with Bashir Salahuddin. The comedic duo wrote, created and star in South Side, which has its Season 2 premiere on Nov. 11.
“We met in college,” Riddle adds. “I think that no matter how many times we might debate about a casting decision or we might debate about a joke in a script, at the end of the day, we spend more time coming up with ideas that make each other laugh than not, and I think that that's the basis of our truly healthy, creative relationship.”
First premiering in 2019 on Comedy Central, the new season of South Side dives right back into the lives of best friends Simon (Sultan Salahuddin) and Kareme (Kareme Young), their co-workers at Rent-T-Own and the surrounding community of Chicago’s Englewood neighborhood.
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Riddle and Salahuddin first met as students at Harvard University and bonded over TV shows like The Simpsons. They went on to write for several years at Late Night with Jimmy Fallon and recently closed a multi-year overall deal with Warner Bros. TV.
With the release of South Side, Riddle and Salahuddin finally get to bring a new chapter of their Chicago-set story to TV. As with most productions during the pandemic, there were setbacks. They had finished writing Season 2 not long before March 2020, but ended up having to dive back into the scripts to be able to move forward. Because they couldn’t hold in-person auditions, they decided to bring back minor characters from Season 1.
“It made South Side sort of like our Springfield from the Simpsons,” Riddle says, explaining characters like the principal from Officer Turner’s high school and the pizza delivery guy will pop up again. He also mentioned Season 2 is full of surprise guests, including Chance the Rapper, Dreezy and Deon Cole.
Diallo Riddle as Allen Gayle in South Side Season 2 Episode 3.
In addition to expanding the show's universe, Riddle describes that while some episodes are “really small and very personal,” a few are “really high concept.” Not being able to give away too many details just yet, he says to keep an eye out for Episode Four, which is based on a famous Chicago movie. Meanwhile, Episode 3 explores Chicago politics, while another is entirely dedicated to a piece of furniture. What’s more, the South Side universe will not be affected by COVID-19.
“I think that Bashir and I are both students of the art and the craft, of writing and performing in comedy. But then on top of that, we’re, I think, very aware of what's going on in the world around us,” he says. “I think that as much as we don't want to be this dated time capsule, and hopefully it won't be dated, hopefully it'll be very timeless— it's still gonna say a little bit about where we were.”
Along with giving the series longevity, not incorporating the pandemic invokes their mission to center joy.
“To outsiders, it’s just, ‘Oh, that’s just the ghetto, it’s dangerous, it’s gang violence.’ That's not what it is,” Riddle says. “I think one of the movies that really influenced us was Coming to America because that was a movie where we saw Black people who were rich and Black people were poor, Black people who were classy and Black people were trashy. You saw all the types of humanity in one group of people sort of ruining this myth that the Black community was this monolithic thing. And I think that that's what we attempt to do on South Side.”
Whether scoping in on the team at RTO, Officers Goodnight (Salahuddin) and Turner (Chandra Russell) or attorney Allen Gayle (Riddle), South Side is laugh-out-loud funny even with its dark undertones.
“It's funny that we call it customer service, when some of these businesses have business models that really hurt people. It's just the nature of this company, RTO, that pretty much everybody who comes through the door, they're gonna basically put you into debt so that you can have a toaster or a TV or an appliance," Riddle says. "We're also making a comment about how companies treat their employees. I love the fact that in the trailer, we had that scene where Jay-Mal (Will A. Miles) finds out the thermostat on the wall is fake and Q (Quincy Young) comes in and says it’s a part of a line of products that are meant to give employees a sense of control.”
“We always want to make you laugh,” he continues, “But while we make you laugh, we try to also get you to think about some things that might slip under the radar otherwise.”
South Side Season 2 will be followed up by the second season of Riddle and Salahuddin’s other series, Sherman’s Showcase, next year. Aside from one big project he can’t reveal details about just yet, Riddle says they are close to doing a pilot for a new TV show starring Marlon Wayans. It would be a nice treat for fans of Netflix’s Marlon, but also would show a side of Wayans “that you have rarely seen on TV.”
For now, Riddle is just relieved to finally be able to give fans new episodes of South Side.
“One thing about our show is that we’re not scared to tackle any side of life in Chicago because we think that the more specific we are with the type of humor that we go for, the more that people will see their own city in Chicago,” he reflects. “I think that we're trying to make something that's universally funny by being extremely specific.”
South Side is streaming on HBO Max.
Photography by: Kevin Scanlon; Jean Whiteside/HBO Max