Welcome back to the South Side. The Chicago comedy, which originally aired on Comedy Central before migrating to HBO Max, is returning for a third season on December 8, 2022. A new trailer for the series promises the same hijinks you know and love while at the same time going bigger and better than ever.
“Shot on location in Chicago, South Side follows two enterprising best friends, Simon (Sultan Salahuddin) and K (Kareme Young), as they hustle and dream their way through the Windy City–when they’re not too busy working as furniture repo men at the local Rent-T-Own,” reads a synopsis from HBO Max. “Featuring cunning Sergeant Turner (Chandra Russell) and her clueless partner Officer Goodnight (Bashir Salahuddin), questionable local politician Allen Gayle (Diallo Riddle), and an ever-expanding roster of real-life Chicago residents, the series offers a glimpse of the lighter side of life in America’s second city.”
South Side residents have a lot to deal with in the new season, including harboring a fugitive, mysterious pothole liquid, and a bedbug outbreak. They’ll also have to deal with the return of villainous Herbert (Chance The Rapper), who crows in the trailer, “Soon RTO will be RT no more.”
In addition to Chance The Rapper, other local legends appearing in the upcoming season include Lil Rel Howery (returning as Bishop), WGCI “Morning Show” host Leon Rogers, legendary Def Jam comedian Adele Givens, rapper Che “Rhymefest” Smith and WLS-TV personality Val Warner, according to the Chicago Tribune.
“Season 3 is going to be a blockbuster,” co-creator Bashir Salahuddin told the Tribune. “We have everything from an homage to Christopher Nolan movies, we have our very first Kwanzaa holiday special. I’m really proud of it because I celebrate Kwanzaa and it’s super funny, but it also honors the holiday.”
“I do think the biggest moment this season, without giving it away, is that we reached out to the kind folks at a tiny little music festival called Lollapalooza,” he adds. “We were able to shoot an incredible piece there including with [rapper and singer] Cordae who was performing. It’s really one of those things that felt like a pie-in-the-sky fantasy when we pitched it in the writer’s room.”