Image via Kevin Scanlon
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
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.”
Right.
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
When did you start production on Season 2?
We started the writer’s room on Season 2 before the pandemic. I remember the first time we were staying late in the writer’s room, and it was actually our director, Michael Blieden, was like, “I think this thing in Iran and Italy”—because that’s where people were talking about it at the time—“I think this thing is going to be a major problem.” I remember the first time we showed up at a Comedy Central core table read of Season 2 was the first time I saw our director wearing a face mask, and I was like, “Oh boy, they’re going to think we’re lunatics.” But it was literally about a week later that everybody was like, “Oh, this is serious.” And I think maybe the week after that, that the NBA, whatever that day was when it was like, “Oh wow, this is really happening.” So we sat on the scripts for a long time, and then it was only when we realized that we were probably going to be able to shoot in April of this year. I’d say maybe it was around January [of 2021], we reconvened the room; it’d been basically a year since we had had the [scripts written]. We opened them up and we knew certain things were going to have to go. We had a whole episode based around the Bud Billiken Parade. We ain’t going to have a parade and hundreds of extras, that’s not happening, so we have to retool the scripts so that you would not realize that we were shooting in a pandemic.
Now, I’ll also say that the pandemic is nothing that we wanted to address in the show. Maybe in one of the future seasons of the show, but we didn’t want to do that [right now]. We wanted to do a season of South Side that didn’t remind you of the pain and the suffering going on in the world right now. So we rewrote the season so that we could still do it, but so that we wouldn’t have to do the pandemic. I feel like a lot of shows were like that. Very few shows want characters walking around in masks.
Right. And if you’re going to do that, it has to be good. I understand the situation, but like you said, people don’t want to watch what they just saw on the news. They want to escape a little bit.
There’s still some escapism, even when you’re dealing with a type of non-escapism, by showing the South Side of Chicago as it really is. It is a funny place that it is in our case. Also, if you’re going to need the mask, we didn’t want to do that show. So we retooled it, and then we got to Chicago in late March, and then we started filming it from mid-April to the top of July. By the time we started filming, most people had started getting vaccines, so we were able to do that whole thing, and we played it very safely. We operated underneath all the safety protocols. I’m happy to say we were never shut down like a lot of shows were. We always made sure that we did everything right. We weren’t shut down. I feel like, for the most part, people didn’t go out and grab drinks after work. We literally played everything safe, so we could deliver the season on time, because it’s been two years since South Side came out, and people on social media made it very clear to me, “Look, I’ve watched the season eight times. You got to give me new episodes to watch.”
When we spoke last time, you mentioned that you and Bashir met while you were singing. That was a big part of the beginning of your friendship. I can’t imagine how much fun you guys had putting together an episode of South Side that is literally a choir competition.
Yeah, man. Bashir and I, we have no problem singing. We couldn’t figure out any reason why Allen Gayle would ever sing, ever, so that wasn’t going to happen. We wanted to come back with something big, and we felt like that was that. Officer Turner and Officer Goodnight, being such important central characters to the show, we were like, “Let’s give him a big episode with lots of Goodnight and Turner, while also maintaining the Simon and Kareem and all.” We also wanted to bring in this great actor, who actually went to high school with Bashir, James Earl Jones II—no relation, but to the eagle-eyed viewers, you’ll notice he’s the same actor who played Berry Gordy on Sherman’s Showcase. He is also in Blockbuster, the musical from Sherman’s Showcase. He’s just a theater-trained savant and he’s really good, and we wanted to play something… You got to have somebody with some singing and acting chops, to go opposite a character as big as Officer Goodnight. We felt like that was really a strong way to go. We also wanted to tackle something that we felt would be a side hustle of Simon, which is the idea that they would try to become sort of ambulance service in their spare time while working for RGL.
Yeah, I was eating while I was watching the first episode. I was not prepared.
I’m not going to say anything about what happens, because some people might read before they watch, but there is some gross stuff in this episode.
Not getting too crazy into this season, but there are moments that felt straight up like, was I watching this comedy set in the south side of Chicago, or am I watching Saw or some darker police procedural? I wonder, are you able to do bigger things like that because you’re now a Max Original? Is the production side bigger?
You know what? No, we didn’t change our process because we were at HBO Max. Obviously, there’s no bleeping going on now. The dialogue is full color, so to speak. But no, we always came into Season 2 wanting to expand the universe of South Side. The same way the first couple of seasons of The Simpsons are all about Bart and Homer and the immediate family. But by Season 8, you’ve gotten to know everybody in Springfield. We’ve wanted to do that with this show. We have whole episodes based around characters, and also non-living characters. We have one episode as an homage to one of our favorite movies of all time. We have another episode that revolves around a non-living character. We have another that takes place at a funeral. I don’t think it’s a spoiler, just saying that we have a funeral episode, and… This is just a tease: We might lose a character. A character from Season 1 may die in Episode 206. I don’t want to give anything away.
We have whole episodes based around people you’ve never seen in Season 1, but we populate every episode with tons of faces that you should recognize from Season 1. One of the fun things that came out of the pandemic is that we had characters who came in just for very minor parts in Season 1. Because of the pandemic, we weren’t able to do in-person auditions, and auditioning over Zoom’s just weird. It’s really hard to get a sense of a person’s energy and their [timing] when they’re just on a Zoom. So what we did was, we did some original casting this season, but we also went back to the actors who we remember did a really good job in Season 1.
Appearing on 'Curb Your Enthusiasm' and 'Insecure'
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.”
Right.
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'
I know that Season 2 of Sherman’s Showcase has been confirmed. Is there any word on when that might be airing?
Yeah, man, I’m very excited to let you know that we are confirmed to shoot in February. We’re shooting Season 2 in February, and we should be able to get it out the door to everybody as early as May or June. Next year we will have Season 2. It always feels like we had a Seaosn 2, but we just did the Black History Month spectacular, which I think is one of the best episodes of Sherman’s, ever.
But yes, absolutely. I’m interviewing members of the crew right now, and we will be back with more mayhem, and I’ve talked with everybody from Fred Armisen to… I want John Legend to perform a song in Season 2. I don’t want to spoil it, but I’ve been in touch with Lil Jon to do a crazy Southern anthem for Season 2 of Sherman’s Showcase. Yeah, we got a lot coming.
I guess Phonte can’t wait to start diving into all those genres, huh?
Man, let me tell you. So Phonte also delivered us a bunch of songs right before the pandemic. Most of them will still be in Season 2. There’s one that I love, that I just feel like SNL kind of beat us to a similar concept, in the year that’s passed since the pandemic. So we might have to retire that song. It kind of breaks my heart. But that’s just the nature of the game. You take a year off and others don’t. Sometimes they might beat you to the punch, but we might be able to repurpose that beat for something else. But let me tell you, we might also record our original idea, and you can decide if it’s better.