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South Side is back on HBO Max with a hilarious season 3

The Chicago-set blue-collar comedy expands its scope while staying true to its jokes-a-minute roots

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Bashir Salahuddin
Bashir Salahuddin
Photo: Courtesy of HBO Max

This year has already seen several great shows with integral settings (see The Bear and The White Lotus, to name two), but there’s a case to be made that HBO Max’s hidden gem South Side might deserve the crown. In its third season, the series (created by Bashir Salahuddin, Sultan Salahuddin, and Diallo Riddle) amps up its ambition, while still putting the residents of Englewood into uproarious situations.

This season’s premiere hits the ground running, reintroducing us to the show’s signature frenetic pace. It opens in the middle of Officer Goodnight’s (Bashir Salahuddin) umpteenth public embarrassment at the hands of a South Side resident, as he’s gotten into some mess when his partner Turner (Chandra Russell) leaves him alone for five minutes. Meanwhile, Simon (Sultan Salahuddin) and K (Kareme Young) are at work repossessing everything in a family’s house, down to the plants and a kid’s graphing calculator. These first six minutes of the season showcase its strengths with mile-a-minute jokes and hints of social commentary, such as a father explaining credit scores as “dark magic.”

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As always, the show populates its episodes with a supporting cast of South Side residents, including both amateur actors and cameos from famous non-actor Chicago natives. The series is a love letter to the city and the everyday workers and hustlers who live in its Englewood neighborhood. And as such, it’s detailed and realistic, poking fun at the mechanics of the city and the different power structures within the community. Bootlicking cop Goodnight and clout-chasing city alderman Allen Gayle (Diallo Riddle) are often the butt of jokes, sure, but just about everyone (even the corny out-of-towners) is treated with some compassion.

Season three still runs in parallel, sometimes-converging plots split between the officers and the workers at Rent-T-Own, but the storylines evolve beyond the show’s traditional formula of R-T-O repossessions and Simon- or Turner-led schemes. Both of the show’s main hustlers are steered toward plots that emphasize their relationships. In the first four episodes made available to critics, Simon steps into situations that bring up existential questions about success and whether the white-collar life would be any different than his current one. Meanwhile, Turner’s exasperating yet fiercely loyal partnership with Goodnight skews further toward the personal with a plot involving his marital strife with his delightfully weird wife Kitty (Rashawn Nadine Scott).

South Side: Season 3 | Official Trailer | HBO Max

This season is also the show’s most ambitious, showcasing absurdist adventures like during its surprising third episode, when a supervillain begins plaguing the South Side during a well-executed homage. The ep recalls season two’s “Life Of An Ottoman,” another outing that drives home how deftly characters can be woven together in the show’s ecosystem. Even though a series taking such big swings could fall into danger of forgetting what made it special to begin with, South Side doesn’t. Many of season three’s surprises are grounded in that they’re referencing films based in Chicago. Even with all of the comedy, the show thankfully remains focused on the city, rewarding viewers who want to stay immersed in the intricacies of that particular neighborhood.

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South Side can be tough to categorize. It’s at once a dual-workplace comedy, an ensemble comedy, and an example of utilizing a setting as an integral character. Now three years removed from its Comedy Central debut, South Side has expanded its reach while still staying true to its roots. R-T-O is still the epicenter (as is the show’s main foursome), but with this latest batch, the series is clearly more comfortable straying out beyond those lines to create something special.


South Side season three premieres December 8 on HBO Max.