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‘South Side’ Review: Chicago-Set Comedy Returns for a Season 2 with Dreams Even Bigger than the City

Now an HBO Max original, these new episodes are true to its workplace comedy roots while taking bigger and wilder creative swings than ever before.

South Side Simon K HBO Max

“South Side”

Jean Whiteside/HBO Max

The season finale of the first season of “South Side” closed with a few friends in a basement, floating away into deep space. It would have been a bittersweet ending for the then-Comedy Central show if it had stopped there, a parting reminder of how big this collection of mismatched employees could go. Fortunately, after a two year hiatus, “South Side” is back — this time as an HBO Max original — and it’s not afraid to keep going galactic whenever it decides to.

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.

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.

South Side Allen Gayle HBO Max

“South Side”

Jean Whiteside/HBO Max

Most of that strength comes from zeroing in on what worked best in the show’s first season. CPD officers Turner (Chandra Russell) and Goodnight (Bashir Salahuddin) return in fine form, taking long enough breaks from roasting each other to prove the other reasons their partnership works so well on screen. Local alderman candidate Allen Gayle (Diallo Riddle) finds more convoluted reasons to be on and around the RTO premises. Seeing more of the off-the-clock lives of Stacy (Zuri Salahuddin), Keisha (Nefetari Spencer), and manager Quincy (Quincy Young) gives the show even more leverage to get more and more abstract with each episode setup.

“South Side” is very much of a piece with “Sherman’s Showcase,” another show with writing partners Riddle and Bashir Salahuddin serving in various on- and off-screen roles. (Eagle-eyed fans of either show might spot an extra cast member crossover or two here in Season 2.) It has the same blend of slipped-in asides (Goodnight and Turner, especially, have dozens of them), where-did-that-come-from one-liners (“Who’s the first person to be fired from Ruth’s Chris for being too creative?”), and meticulous converging plot points. There’s a blend of the spontaneous and the carefully sharpened kinds of comedy that keep any viewer on alert. For season-long looks at a single collection of characters, the fact that many of the central on-screen “South Side” players are also writers gives the show a connected, communal sketch show troupe feel.

With that much vignette-y DNA, some of these setups feel the stretch when filled out to half-hour length. But even when the jokes don’t land quite as hard, “South Side” is a show that always commits. Look away for a few minutes and you might come back to a show that suddenly has a handful of wild animals or a comically grisly eye injury or a group of vengeful clowns, perfectly at home in a show that knows how to accommodate any and all of them.

Just because the show ventures a little further from RTO than in the first season, Season 2 isn’t ignoring the area-specific details that set those episodes apart. No one is more than a few degrees of separation away from anyone else, and “South Side” has fun coming up with ways for all these people’s circles to intersect, at dance competitions or citywide elections or at their kids’ swimming lessons. A late-season episode focuses on work breaks, but this show mainly uses its time inside RTO as a reminder of all the reasons why these employees value their time outside their jobs. You could call “South Side” a workplace comedy, but like the place it’s set, if you’re only looking in one place, you’re missing so many of the things that make it stand out.

Grade: B+

The first three episodes of “South Side” Season 2 are now available to stream on HBO Max. New episodes will be available the following two Thursdays. 

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