Dillon is a writer, and a lover of storytelling and creativity across all mediums. He studied Film and Digital Media at UC Santa Cruz, where he became a voracious consumer and ponderer of the creative arts. He has a background in screenwriting, as well as freelance film theory and pop culture journalism. Dillon connected to the inclusive, empowering mission statement of TheHollywood Insider, because of his shared belief in the power of storytelling, and its facility to engender empathy and understanding, as well as entertain. He believes in finding joy and purpose through making, watching, discussing, and dissecting the diverse collection of creative media that inspires him. He has particular interest in stories that come from largely unheard, historically excluded perspectives.
Oct 13, 2022
Table of Contents
Photo: ‘South Side’
‘South Side’is a glorious anomaly within the usually predictable, and the larger landscape of half-hour TV comedies that exists today. Fans of the show rejoiced earlier this year when the news broke that the series was indeed being renewed for a third season. Originally airing on Comedy Central, but making the jump to HBO Max after its first season, the Chicago-based sitcom quickly developed a passionate and steadily growing cult following. The strength of the show’s writing and casting is simply undeniable. A truly homegrown product, ‘South Side’was conceived by two brothers who are native to Englewood, a neighborhood on Chicago’s titular South Side. Bashir and Sultan Salahuddin, along with Bashir’s longtime writing partner Diallo Riddle, write, produce, and act in the series themselves.
The ensemble comedy is centered on the story of Kareme and Simon, two lifelong best friends and recent community college graduates. Because they share one another’s boundless passion for upward financial mobility, much of the humor and the heart of the show is rooted in watching the entrepreneurial duo hatch one hair-brained get-rich scheme after another. But before they can hit the big time, the pair of lovable hustlers are stuck working for Kareme’s brother Quincy (played by his real twin brother) at his furniture repo business, Rent-T-Own. So few original comedies, especially ones that are as uncompromising and authentically funny as this one, are given the chance to grow over multiple seasons. Luckily, it looks like this farcical yet grounded Chi-town sitcom is getting just that.
The show somehow manages to be the most charming, heartfelt comedy currently airing on TV, while still containing a number of the filthiest, most ludicrous gags and comedic set pieces that have ever made their way into the somewhat traditional sitcom format. When asked about the initial creative approach while writing the show, both Salahuddin and Riddle cited Matt Groening’s ‘The Simpsons’ as a major influence, and a kind of tonal touchstone for the comedic DNA of ‘South Side.’ This adherence to some of the classic tropes and character dynamics of TV sitcoms with deep rosters of wonderfully bizarre side characters, like ‘The Simpsons,’ gives the show the ability to follow any number of unexpected storylines in any given episode. One exemplary ‘South Side’ storyline follows a group of characters as they have the south side equivalent of ‘Ferris Bueller’s Day Off.’
Another follows the circuitous journey of a hand-me-down ottoman, and how it traveled across the south side and beyond before inevitably making its way back home to Rent-T-Own. As the audience, we never really know which combination of riotous characters will be interacting at any given time, or what south side-specific location, theme, or topic the comedy will be ingeniously drawn from next. This sense of narrative freedom is more than justified by the show’s seemingly endless supply of cackle-inducing dialogue, absurd but gripping scenarios, and distinctly drawn side characters all of which are perfectly crafted for the show’s stellar cast of comedic players to execute. ‘South Side’ smartly plays by the conventions of other TV sitcoms that it clearly admires from the past, but the writing also simultaneously infuses an extremely modern sense of humor and a series of cultural reference points that keep every episode feeling incredibly fresh at the same time.
At the risk of making the rest of this article solely consist of a lengthy column of actors’ names and the corresponding indelible characters that they portray on the show, here are a handful of cast members who, among the many others, stand out. Watching Bashir Salahuddin’s Officer Sandy Goodnight, (an officer who has been recently transferred from the nicer side of town to the notoriously rough south side), discover new ways to be made apoplectic, uncomfortable, or bewildered by the culture shock that his new jurisdiction provides, truly never gets old. Goodnight’s wisecracking partner in the show, Officer Turner, is played with effervescent sass and irresistible swagger by Chandra Russel, who interestingly, is Salahuddin’s partner in real life. The bitter professional rivalry between Diallo Riddle’s scheming Allen Gayle and ‘Bust Down’ co-creator Langston Kerman’s unctuous Adam Bethune, is a deliciously petty game of political back-and-forth that persists throughout the series.
The list of hysterical side characters goes on from Travis, the absurdly derivative aspiring “generation-defining” struggle rapper, to Bluto the soft-hearted, laconic philosopher thug, to Keisha, a disgruntled Rent-T-Own employee who is dead set on getting her visibly disinterested son into the NBA by the time he graduates, just to name a select few. The show almost exclusively casts performers who were actually born and raised on the south side of Chicago. Whether it be undiscovered first-time performers like Kareme and Quincy Odom, or instantly recognizable comedy stars like Lil Rel Howery, nearly everyone we see on ‘South Side’has a tangible, real-life connection to the place that they are representing and performing in. That’s why each character feels so authentically real and specific in their mannerism, world-view, and interests.
In addition to the incredibly varied mural of humorous characterization that it paints, the show also engages in some legitimately astute social commentary. The writers cleverly parody numerous trending topics and controversies that are currently happening in Chicago’s south side and across pop culture, with remarkable insight and aplomb. The “Litcoin” episode, where a local self-described bitcoin czar, gets some major traction on his breakout crypto-currency hilariously named Litcoin, only before he is kidnapped and held for ransom by LaRoyce Owens’ heady neighborhood drug dealer, and mercilessly interrogated on what his ethos will be as a “the next Zuckerberg-type,” stands out in this respect.
The episode entitled, “The Day the Jordans Drop,” where the very foundations of the neighborhood threaten to crack over who will receive the final pair of Air Jordans that are being released in an exclusive drop at the local sneaker shop, stands out as well. In a way, one can think of ‘South Side’as a much sillier, crosstown sister show to Hulu’s ‘The Bear.’ The two shows echo each other less in tone, and more in their respective ability to paint a portrait of a culturally-specific community of people who live and often work together, and showing the inherent drama and comedy that comes from a group of people trying to coexist in the windy city.
So go ahead and catch up on the first two seasons of ‘South Side’ if you happen to be an HBO Max subscriber. And whenever the third season of this gem of a comedic ensemble premieres, make sure to give it a shot for all the reasons stated above. But most of all, you should tune in simply because original comedy series that contain this combination of sheer comedic firepower, and a completely distinct perspective, do not come around very often. So when they do, they deserve to be seen.
By Dillon Goss-Carpenter
Click here to read The Hollywood Insider’s CEO Pritan Ambroase’s love letter to Cinema, TV and Media. An excerpt from the love letter: The Hollywood Insider’s CEO/editor-in-chief Pritan Ambroase affirms, “We have the space and time for all your stories, no matter who/what/where you are. Media/Cinema/TV have a responsibility to better the world and The Hollywood Insider will continue to do so. Talent, diversity and authenticity matter in Cinema/TV, media and storytelling. In fact, I reckon that we should announce “talent-diversity-authenticity-storytelling-Cinema-Oscars-Academy-Awards” as synonyms of each other. We show respect to talent and stories regardless of their skin color, race, gender, sexuality, religion, nationality, etc., thus allowing authenticity into this system just by something as simple as accepting and showing respect to the human species’ factual diversity. We become greater just by respecting and appreciating talent in all its shapes, sizes, and forms. Award winners, which includes nominees, must be chosen on the greatness of their talent ALONE.
I am sure I am speaking for a multitude of Cinema lovers all over the world when I speak of the following sentiments that this medium of art has blessed me with. Cinema taught me about our world, at times in English and at times through the beautiful one-inch bar of subtitles. I learned from the stories in the global movies that we are all alike across all borders. Remember that one of the best symbols of many great civilizations and their prosperity has been the art they have left behind. This art can be in the form of paintings, sculptures, architecture, writings, inventions, etc. For our modern society, Cinema happens to be one of them. Cinema is more than just a form of entertainment, it is an integral part of society. I love the world uniting, be it for Cinema, TV, media, art, fashion, sport, etc. Please keep this going full speed.”
south side, south side, south side, south side, south side, south side, south side, south side, south side, south side, south side, south side, south side, south side, south side, south side, south side, south side, south side, south side, south side
Dillon is a writer, and a lover of storytelling and creativity across all mediums. He studied Film and Digital Media at UC Santa Cruz, where he became a voracious consumer and ponderer of the creative arts. He has a background in screenwriting, as well as freelance film theory and pop culture journalism. Dillon connected to the inclusive, empowering mission statement of TheHollywood Insider, because of his shared belief in the power of storytelling, and its facility to engender empathy and understanding, as well as entertain. He believes in finding joy and purpose through making, watching, discussing, and dissecting the diverse collection of creative media that inspires him. He has particular interest in stories that come from largely unheard, historically excluded perspectives.
Dillon is a writer, and a lover of storytelling and creativity across all mediums. He studied Film and Digital Media at UC Santa Cruz, where he became a voracious consumer and ponderer of the creative arts. He has a background in screenwriting, as well as freelance film theory and pop culture journalism. Dillon connected to the inclusive, empowering mission statement of TheHollywood Insider, because of his shared belief in the power of storytelling, and its facility to engender empathy and understanding, as well as entertain. He believes in finding joy and purpose through making, watching, discussing, and dissecting the diverse collection of creative media that inspires him. He has particular interest in stories that come from largely unheard, historically excluded perspectives.
