HBO Max comedy series gets canceled after three seasons

Plenty of films and shows are set in Chicago. The city has a certain aesthetic that filmmakers and creatives are drawn to. In 2008, fans were thrilled to see “The Dark Knight” present the streets of downtown on the big screen — even if the setting was based in Gotham. 

Directors and filmmakers have been using the streets of Chicago as a setting since 1896, but how many of these films and shows felt like an actual representation of the city and the culture? Chicago is on the big screen, but often the story is only told from a downtown point of view. 

“South Side” was a show that gave viewers a taste of the city beyond the Bean, Millennium Park or State Street. The creators of the show made it their mission to showcase the South Side of the city.

“South Side” started off on Comedy Central, but after a cancellation, HBO Max picked it up for season two in November 2021. After three seasons, the network announced they will not be picking up the show for a fourth season — regardless of its popularity. 

“This is one of the most hilarious shows I ever watched. I feel like I am getting a window view inside Chicago the way I thought ‘Insecure’ gave the world a look into L.A. and the little things our culture does day to day,” Trevon Williams said. 

Williams — a resident of Los Angeles — became a fan of the show after his Chicago native friends spoke highly about the show’s comedy and premise. His first impression of the series was so captivating that he binged the entire show, but he has nothing to look forward to beyond the third season. 

“I was distraught. It was hands down the funniest show on TV with the best collection of characters,” Williams said. 

The creators of the show, Bashir Salahuddin and Diallo Riddle, based the show on the running thread of what goes on at the Rent-T-Own store. Aside from a look at the employees at the store, the show also follows the tales of two police officers and a comedic view inside Chicago politics. 

Part of the reason creativity and accuracy were never an issue for this cast is that two of the creators were born and raised on the South Side. They used first-hand knowledge to give viewers an honest and original perspective of the city. They wanted everything to be authentic from the writing to the setting, and even the actors and extras. 

“I’ve always been interested in acting … I like the show. It’s about the South Side of Chicago. I have a very particular look, I’m a rapper. So, I figured it’s a Black show, I have a way better chance of getting picked up than I do on a white show. Because I don’t look like an extra for a white show,” Deem Beamon said. 

Beamon – also known by his stage name Cantbuydeem – tried out to be an extra on the show and appeared in a scene in season three, episode two. Although he only had a brief role as an extra, he still felt the camaraderie of everyone on set. 

“Everybody who was working on the show was really cool … the people who worked for the show, the people that were actually on camera, they were always really cool … and very welcoming. And they seem like they were just happy to be here,” Beamon said. 

Beamon even got a chance to bump into one of the creators, Bashir Salahuddin, during some downtime and engaged in traditional Chicago “roasting season.” Coming back to the set the next day, Salahuddin remembered him and said it was “good to have him back and good to see him.” Beamon couldn’t believe that one of the stars actually recognized him. 

Aside from feeling like a family member on the set, Beamon appreciated the show for what it represented and stood for. 

“They captured the funny side of the hood … and it was a little outrageous because it’s a comedy. But it just was very authentic. It felt like they spent time with the people, like they really went through the neighborhoods,” Beamon said. 

Chicago viewers and West Coast fans had high hopes for future seasons. Viewers like Sean Barker even hope the show will eventually resurface. 

“I was pumped for a fourth season. Knowing that the show has jumped networks before keeps me in good spirits. Too much talent on the table … I think networks know how loved the show is, it’s just a question if the next network will let the crew keep the creative freedom they had so far,” Barker said. 

The show didn’t try to conform the South Side to what they thought people wanted to see. It let the neighborhood speak for itself. Chicago will continue to be a popular city and hopefully future creators will try and follow the example “South Side” set. 

Header illustration by Julia Hester