Two summers ago, actor-writer Diallo Riddle was at the helm of two new series, Comedy Central’s South Side and IFC’s Sherman’s Showcase. In that timeframe, Sherman’s dropped a hilarious Black History Month Spectacular and South Side became an HBO Max Original. Really dope when you can see a comedy rooted in the Black experience in the south side of Chicago getting put on this kind of platform early into its run.

After taking in a number of episodes from Season 2 of South Side, which premiered on HBO Max on Nov. 11, Complex got to hop on the phone with Riddle about what he’s gotten into since owning all Summer ‘19. From the increase of exposure given to South Side the moment it touched HBO Max to how they worked (and reworked) the season due to the pandemic to some of the insane moments you can find in the first three episodes of the season to teases of what’s still in store. Riddle also spoke on his guest appearances on Curb Your Enthusiasm and Insecure, as well as an update on the long-awaited second season of Sherman’s Showcase. Here’s everything you need to know about the second season of one of the funniest shows you better be watching.