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South Side proves you can make a great Chicago show that’s also a smart blue-collar comedy

The second season of Bashir Salahuddin and Diallo Riddle’s sitcom debuts on HBO Max with even more love for the Second City

TV Reviews South Side
South Side proves you can make a great Chicago show that’s also a smart blue-collar comedy
Kareme Young and Sultan Salahuddin in South Side Photo: Jean Whiteside/HBO Max

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. 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?”).

The first season of the sitcom, created by Diallo Riddle, Bashir Salahuddin, and Sultan Salahuddin, made its home on Comedy Central, but has moved to the premium streamer for its second go-round. And that new location comes with changes to the overall flow of the show. While the series still focuses on the adventures of Simon and Kareme (played by Sultan Salahuddin and Kareme Young, respectively), two employees of a rent-to-own furniture business, we get to see more of their side hustles in action.

The recent community college grads are street entrepreneurs, and their co-workers have plenty going on while they’re supposed to be working as well. We also get to see more of Officers Turner and Goodnight (real-life married couple Chandra Russell and Bashir Salahuddin) and their on-the-job hobbies. Well, more so Officer Turner’s; Goodnight is almost never involved on purpose.

South Side is filmed in Chicago’s Englewood neighborhood, a part of town that is often used as a dog whistle by people whose idea of Chicago is fully formed by negative attention from bad faith actors in the national mediasphere. Here, Englewood isn’t used as a prop to represent violence. Its portrayal is as realistic as has ever been depicted on television, and even its less-savory aspects are shown through a lens of comedy.

The Salahuddins and most of the cast are actually from the South and West Sides of Chicago, and it’s evident in everything from their choices in exterior locations to the hyper-local references. There’s a moment in episode one, where a woman is being called stuck-up and is asked if it’s because she went to Kenwood or Whitney Young High School. So many confident Chicago women have been asked this question countless times.

The creators’ and writers’ love for Chicago, especially Black Chicago, is made clear in season two. South Side does not treat Blackness as a monolith, nor does it use it as a punchline. This is not a minstrel show made to entertain white audiences with performative Blackness. This is the slice-of-life, blue-collar comedy Chicago Party Aunt only wishes it could be.

South Side’s guest appearances are also very Chicago—it’s clear that the city’s famous and soon-to-be famous folks were paying attention to season one and were eager to join what looks to be a fun day on set. Comedians, rappers, and local actors have always made cameos, but someone finally got Chance on the phone, and that’s as 2021 Chicago as you can get.

Part of the charm of South Side also lies in other ensemble comedies like Cheers and NewsRadio: They’re all workplace-driven, but at their cores are about the different, often super-weird personalities that come together when everyone is forced to assemble for eight hours a day. South Side takes characters that would most likely be painted with a broad brush by a non-Chicago, non-Black writing staff and gives them nuance. Not every Black girl from around the way is the same, and we get to see that. Not every Black police officer is the same, and we get to see that. Hell, the lifestyles of the characters played by Kareme and Quincy Odom prove that not even every identical twin is the same. (Labor versus management can tear a family apart!)

South Side builds upon the rich personalities of the residents of Englewood we were introduced to in the first season, and finds even more to dig into in the second. While the jokes are truly so Chicago, they are also so relatable in their context. The series is a love letter to a city and the parts of it that outsiders have made the rest of the world look down upon. It’s one part middle finger to those people, and two parts really, really funny.

15 Comments

  • StoneMustard-av says:

    Just finished the first season a few days ago and WOW. Better than the hype. Kind of an easy comparison (former Comedy Central series filmed on location in a Midwestern city that is also used as a racial dog whistle) but it reminded me of Detroiters. In that it’s very joke-dense with a lot of hyper-specific references that are also pretty universal somehow. I’m excited for S2 and I’m glad they’re going to do something with Kareem and Q’s whole dynamic (living with your boss who is also your brother sounds like it would be the worst thing imaginable.)

  • DudleySpellington-av says:

    I was impressed by the hyper specificity. There’s a gag about the Northwest suburb where I grew up that even people from Chicago area might not immediately recognize. 

  • elloasty-av says:

    I described this show to someone as “The Wire if it were played for laughs”. Simply because it was difficult to recommend and explain why it was so funny. It really does have concurrent story lines that go between the street, the police, and local level politicians. The characters are all great but it is tied to the identity of the city where it’s set.

  • eatmorepez-av says:

    My Top Five complaints most Chicago movies and TV shows not called South Side, get wrong about the city. 1. “DA’s Office.” There is no DA or District Attorney anywhere in Illinois. Each county has a State’s Attorney that prosecutes crimes.2. “License and registration” Police in Illinois ask motorists for their license and proof of insurance during traffic stops, not the vehicle registration.3. Not every Chicagoan lives in an apartment building across the street from Wrigley Field4. The worship of Deep Dish pizza. The vast majority of Chicagoans eat thin crust pizza on a regular basis. Some never eat deep dish or only when people from out of town come to visit.5 Hot dog carts. There are NO FUCKING HOT DOG CARTS on the streets of Chicago! This is an NYC trope. For the love of God, please stop doing this in Chicago movies and TV shows already!

    • frankwalkerbarr-av says:

      Yeah, I think Chicagoans (and Chicago-adjacent people) defend deep dish mostly as a reaction against New Yorkers who constantly claim that “it isn’t pizza” or some such nonsense. In practice, thin crust pizza is more common everywhere.

    • nicktaylor63-av says:

      Your point related to the thin crust vs deep dish debate resonates with me as I am a Chicagoan who lives in Asia, so I need to explain the truth about our pizza preference at least once per month. I even show them photos on the web of how we cut our pizza into squares rather than into hulking triangular pieces. I am rewatching season 1 of the show and it still cracks me up. The jokes are so specific that it seems like a Chicago version of Desus and Mero wrote them. Season 2 is a strong follow up to season 1. One of the other commenters referenced Detroiters and I have to agree that the two shows have similar DNA. However, I do hope South Side will get a third or fourth season.As someone who has a ton of family in Chatham, South Shore, Roseland, Englewood it was amazing to see these neighborhoods (and others) represented in the show in a way that highlights the people and spaces rather than other stuff that tends to get publicized in news stories. On a side note, I stumbled across this companion web series which I decided to share here:Lastly, it is ALWAYS time for the percolator. 

  • amessagetorudy-av says:

    From the moment I watched the first few episodes of the first season, I realized I found the rare Chicago show that “got it.” It’s the Chicago show I’ve been looking for… one that acknowledges the trouble, sure, but also the humor, heart and the things that make it Chicago. And it shows the part of Chicago I spent most of my time in – the non-descript neighborhoods that don’t contain local identifiers (“Hey, look, a deep-dish pizza joint run by a guy wearing a Cubs jersey…”) but that I can recognize instantly (even though I grew up in Morgan Park and not Englewood). Shit isn’t perfect, but real people live there and – surprise – get up and go to work everyday just like everybody else. I’ve introduced it to friends in my new city (I moved away about 10 years ago but grew up there and lived there for more than 40 years.) and even they think its hilarious. I actually get homesick watching it.And I made it through the first 10 minutes of Chicago Party Aunt before turning it off. It’s the “Chicago” that people not from Chicago think is Chicago. And I don’t care WHO created that show and why.

  • disqusdrew-av says:

    Glad its got a 2nd season somewhere, but its still annoying Comedy Central keeps jettisoning its original programming elsewhere (this, The Other Two, etc) so they can be a 24 hour rerun channel

  • taumpytearrs-av says:

    They definitely made a show that feels specific but is still broadly appealing, because I am a white guy who has never been to Chicago and I think its hilarious. And as someone who has spent their whole adult life grinding at shitty jobs with other struggling people who are still funny and weird in the face of life’s difficulties, it feels more real and relatable than so many other shows. My brother-in-law even worked for Rent-a-center for a few years! Favorite first season eps, everyone? The episode with Officer Turner and the TV cop’s weave was one of the funniest things I watched this year.

    • dennycrane49-av says:

      The courtroom episode with testimony about counterfeit Bill Cartwright jerseys was the season one highlight for me.

  • grant8418-av says:

    S2 is just as great as S1

    Now I just need more Sherman’s Showcase

  • almightyajax-av says:

    “Man, fuck Kanye! I don’t mean that. Yeah I do!”

  • pinkiefisticuffs-av says:

    Have not watched this and may never get around to it, but I’m curious about the rent-to-own furniture business aspect.  Is it presented as a way to horrifically gouge poor people, or does it get white-washed?

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