'South Side' Co-Creator Diallo Riddle Talks Season 2 and Appearances on 'Insecure' and 'Curb Your Enthusiasm'

'South Side' co-creator Diallo Riddle talks about the move to HBO Max, Season 2, and recent appearances on 'Curb Your Enthusiasm' and 'Insecure'.

Diallo Riddle 'South Side' HBO Max Original Season 2 Interview

Image via Kevin Scanlon

Diallo Riddle 'South Side' HBO Max Original Season 2 Interview

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.

'South Side' Becoming a Max Original

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It’s been dope to see see the series make that transition from Comedy Central to becoming a Max Original. Can you talk a little bit about that process and transition from one network to not just a new network, but this big emerging network?

Well, the funny news, khal, is that I got a phone call one day and heard it was happening. [Laughs]

I figured. [Laughs]

Every now and then you do feel like a cog in the machine, but for real, we can’t be happier to be on HBO Max. We love Comedy Central. That was the place that made our pilot and made our first season of the show. But it’s incredible, the amount of exposure you get on a streamer these days. When we were on Comedy Central, definitely we were getting some love. The second South Side popped up on HBO Max, it shot up to a whole different level of exposure. And as a creator of a show, we do these shows so that people will watch them. It’s very clear to me, that as a creator, you want your show to be streaming somewhere people will see it. It’s almost wild to me that places, as recently as when we talked two summers ago, would say, “Hey everybody, this show is going to come on at 10:00 PM, on this one screen in your house.”


That’s wild to me. I’m mean people watch television shows on their phone, in bed at 3:00 in the morning. The idea that we should control when people view the content, is just really old school. I understand why it exists, but it definitely felt good when we debuted on HBO Max, and when HBO Max said, “In Season 2, you’re going to be a Max Original.” We were really excited because we feel like this is the platform for our comedy, to get it out to people all over the planet. HBO Max is expanding. It’s an exciting time. I think Max, Netflix, and Disney+ are some of the best streamers with some of the soundest business models out there. So we’re happy to be a part of that.

Working on 'South Side' Season 2

South Side Season 2, Episode 3
Kareme Young, Sultan Salahuddin, 'South Side' Season 2, Episode 3

Appearing on 'Curb Your Enthusiasm' and 'Insecure'

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South Side moves to HBO Max last year, and I remembered that right at the beginning of the quarantine, you were in the last episode of Curb Your Enthusiasm, last season?

It was the last episode, last season. Yeah, that sounds right to me. Look, man, I haven’t ever said this to anybody, but I’ll go out and share with you, because it’s something I think about any time I watch or someone says they love Curb Your Enthusiasm.

Thank you.

I grew up as a comedy writer, so to speak. I grew up idolizing Larry David. He’s one of my heroes. Seinfeld was such a big thing in my family, and Curb Your Enthusiasm was such a big thing. Just Larry’s style of humor is such a big thing, so imagine my excitement when my agent calls is like, “Hey, I got you a part on Curb Your Enthusiasm. You’re going to play a fireman.”


I was like, “You’re lying. This is one of the happiest days of my life.” I actually did research on firemen, so I could actually throw out some firemen lingo. One of the things that I found out is that believe it or not, firemen in almost every district, in every jurisdiction, or whatever you want to call it, they don’t have beards. They don’t have beards because it doesn’t allow the seal to completely close off the mouth area when they have to go into the fire. I know that I have a beard. I wasn’t going to cut my beard for one day of shooting. I was a little bit like, “Oh man, the second I show up in this fireman outfit with a beard, people are going to know that I’m inaccurate.” It might have been a little bit in my head.

I knew what the scene was supposed to be about. It was supposed to be about Larry opening up the spite coffee store, next door to Java Joe’s. Again, this is my hero. It made me a little bit nervous. We shot the scene, but I can honestly say nothing funny came. Nothing funny came to me. I feel like Larry was standing around trying to figure out what’s funny about this scene again. We were going to do this whole riff about, “Why are there no Black presidents on the wall? You got Jefferson and Washington.” We did it. It was okay, but you could tell it wasn’t hilarious. 

Then the scene aired, and I was like, “Man, I was on Curb Your Enthusiasm, but I don’t even get to be a part of a classic Curb moment.” It’s haunted me ever since that day. It’s just one of those actor things, especially when there’s not a script. People may not know this, but there’s never a script for Curb Your Enthusiasm. You’re just supposed to go in and riff with Larry, and they would just save the funniest stuff. There was just nothing funny that really happened that day between us, and I was crushed. I’m driving home from the set that day, just dead inside. Just that crushing feeling, “Man, I had a chance to do a see with Larry David and nothing. Nothing.”

Fast forward, about two years later, I get another call from my agent, “Yo, you’ve known Issa for years. She wants you to do Insecure.” I go to that set and granted, this time there’s a script, so it’s already a little bit different. I sit down on set, and we rehearse the scene, and it’s already kind of funny, and expertly written by my friend, Amy Aniobi. But let me just say this, by the third take, me and Issa were cracking up. You could tell what I was giving her, what she was giving me, there was a chemistry there. By the time I left that set, it was such an opposite feeling, driving home. Wow. From the ad-libs to the improv, to the lines that were written. It was getting funnier as we did more and more times. It was just the complete opposite.

Here are two HBO shows that I love, Curb Your Enthusiasm and Insecure, could not have had a different experience shooting both. I still kind of want to run into Larry one day, and just be like, “Yo, I don’t know what was up that day.” Because I don’t think he would fault me. I actually think that he was just in a quiet, sort of subdued mood that day, too. We want to think that we can always control these things, but especially when there’s no script involved, and no real roadmap, I just feel you’re going to have some on days, you’re going to have some off days. I’m learning how to not beat myself up about that Curb appearance, but I think the Curb appearance has helped me a lot.

Maybe you can hit up Larry. Maybe there’s another fire. [Laughs]

Absolutely. I know the head showrunner of that show, and I’ll just be like, “Hey, maybe the fireman shows back up. Come on Larry. Hey, the fireman’s back.” [Laughs] Seriously, I am just a huge fan of that show. I have a million Curb Your Enthusiasm ideas. Maybe one day I could just pitch him an idea, and say, “And then at the end, the fireman shows back up.” [Laughs]

The Future of 'Sherman's Showcase'

Sherman's Showcase

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