South Side takes even bigger and wilder creative swings in Season 2

Indiewire

"Most of South Side still revolves around the employees of Rent-T-Own, a store that loans out everything from end tables to TVs to household appliances. In their downtime at work, Simon (Sultan Salahuddin) and Kareme (Kareme Young) are usually deep into some plan that will be their ticket to a new job, better conditions at their current one, or (as is the case with the show’s triumphantly goofy Season 2 premiere) a few high-quality steak dinners for the rest of the year," says Steve Greene of the HBO Max comedy. "It’s that blend of retail job frustration and the constant presence of the absurd that makes South Side a reliably unpredictable treat. The longer the show has gone, the more the employees, customers, and other neighborhood fixtures have gone from dependable punchline deliverers to vital parts of whatever the Rent-T-Own atmosphere manages to spit out on any particular day. Sometimes it means traveling with Simon and K as they take back items from people late on their payments. It could easily mean following them as they double book their delivery truck as an affordable ambulance. Season 2 takes those possibilities even further, packing an impressive midseason run with episodes that have basic connections to RTO before heading in an entirely different direction. A half-hour alternate take on an iconic ‘80s classic, an episode-long saga of a single piece of furniture, and one very extravagant sendoff to the city’s most beloved party promoter is the best threepeat that Chicago’s had in almost a quarter of a century."

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• South Side is the rare Chicago-set show that feels uniquely "Chicago": "From quirky comedies like Easy and Man Seeking Woman, to gritty dramas like The Chi and Lovecraft Country, Chicago is the city that works… well as a backdrop," says Jill Hopkins. "But the thing about so many of those series, and even the Dick Wolf-created Chicago shows, is that they could be set anywhere. Rom-com situations can and do happen anywhere. Corruption and racism exist everywhere. There are so few shows set in Chicago where the city feels like a character, where the writing lands both because and in spite of its specificity. HBO Max’s South Side is the rare show that meets that criteria ('Chi-teria?')."
• South Side co-creator Diallo Riddle is amazed at the difference between being on Comedy Central vs. HBO Max: "Every now and then you do feel like a cog in the machine, but for real, we can’t be happier to be on HBO Max," says Riddle. "We love Comedy Central. That was the place that made our pilot and made our first season of the show. But it’s incredible, the amount of exposure you get on a streamer these days. When we were on Comedy Central, definitely we were getting some love. The second South Side popped up on HBO Max, it shot up to a whole different level of exposure. And as a creator of a show, we do these shows so that people will watch them. It’s very clear to me, that as a creator, you want your show to be streaming somewhere people will see it. It’s almost wild to me that places, as recently as when we talked two summers ago, would say, 'Hey everybody, this show is going to come on at 10:00 PM, on this one screen in your house.'"