Filmed and set in the Englewood area of Chicago, it follows two friends (portrayed by Sultan Salahuddin and Kareme Young) who recently graduated from community college and are seeking business success while working at a rent-to-own shop.

[7] South Side centers on "a pair of newly minted community college graduates and small-time hustlers who are always cooking up some petty scheme from black market Viagra to street corner popcorn — with an eye toward upward mobility".

[8] On October 17, 2017, it was announced that Comedy Central had ordered the pilot for South Side from creators Bashir Salahuddin and Diallo Riddle, writing alums from Late Night with Jimmy Fallon.

[31] Other cast members and guest stars include Chicago natives Lil Rel Howery, Nathaniel "Earthquake" Stroman, LisaRaye McCoy, Chance the Rapper, and Kel Mitchell.

"[31] Tambay Obenson wrote in a review for IndieWire, "The creators and cast know this world intimately, and instead of turning their camera on the usual crime and poverty, they find the humor that exists within the mayhem.

[35] On September 4, 2019, Comedy Central and WBEZ Chicago launched South Side Stories, a podcast collaboration that centers the real-life people and places that inspired the series.