"We convinced the networks to help us make these sizzle reels—these proofs of concept," Salahuddin explained to ROCK THE BELLS. "If I give somebody a piece of paper and say 'this character is going to be played by Eddie Murphy.' When you read it, you hear Eddie in your head, so you know how those jokes are going to hit. If I give you a piece of paper and say 'this guy is going to be played by this dude I went to high school with on the Southside of Chicago.' I promise you, a white executive is not going to hear that correctly. I don't know how that sounds in their head! And to be fair, if they gave me a piece of paper and said 'hey, this is my buddy from high school,' I wouldn't know how that shit sounds either!"

IFC became the network home for Sherman's Showcase, a parody musical sketch variety show hosted by the fictional Sherman McDaniel (Salahuddin), taking viewers through the show's lengthy decades-long library of musical and comedic performances. Music is such an integral part of the comedy, and rapper/singer/songwriter Phonte is the architect of Sherman's... brilliantly parodic songs. Moments like "That Ain't Right" and the infamous "Drop It Low For Jesus" were born of his unique brand of humor and musicality. For Phonte, it's like a test for his musical knowledge and motivation to step into the shoes of different eras and different stylistic approaches to recording.

"When you're working on your own music, you just kinda might have your own set of equipment that you use, just different technical tools...to fit what you're doing," he explains. "With Sherman's... it's almost like you're playing dress-up. It forces you to use another set of tools. If Diallo says 'hey, we need a song that's like a 1970s Meters-type joint,' then I actually go and listen to a Meters record. And me and [musician and Phonte's frequent collaborator] Zo! will sit there and look up 'what kinda mic did they use on this?' and 'how did they mic that snare?' Its music nerd shit to the highest power. Working on Sherman's... gives me another skill set to use, so when I come back to my music, I have a whole new set of tools to play with. It sharpens me in a lot of ways."

Riddle and Salahuddin honed their unique comedic sensibility together, first as college collaborators, then as co-writers for Fallon, and now, their projects like Sherman's Showcase and South Side showcase that distinct blend of the duo's idiosyncrasies.

"We usually have the same goal in mind," says Riddle of the two men's working relationship. "To make something the best, the funniest, the most everlasting—that's always the goal that we go for. I think as we've expanded our production company, all we've done is try to make each other's dreams come true. Or to empower those writers' in the South Side room or the Sherman's Showcase room; [to] try and make the ideas that they've been thinking about for years and years come true."

Having spent more than 15 years in writer's rooms for shows like ...Fallon and David Alan Grier's Comedy Central series Chocolate News, Riddle and Salahuddin saw firsthand how collaborative comedy has to be. That spirit of togetherness fuels the comedy on Sherman's Showcase; both the hijinks on-camera and the creative approach behind it.

"I think we understand process," says Salahuddin. "For example, I do feel like successful comedy, in my personal experience, is always a collaborative process. It's always a lot of people putting in. Not too many people, but it's the right people and it's funny people. They're the reason that most successful comedies have writer rooms full of funny people."

The metric is simple: make each other laugh. It's not just about what you may find funny, but how much you can get the room to share in that moment. For Salahuddin, that is imperative to putting a show together. "When you're trying to make strangers laugh—which is what comedy is, you're trying to make a stranger laugh who does not know you and has no incentive—how do you find out what might be funny? When you get funny people together, they kinda make each other laugh. And if funny people can make each other laugh, usually, you're kinda on to something. And I think both Diallo and I understand that. We understand the process. We understand that it takes lots of revisions for something to go from being kinda good to ready to air. And you can't rush that process. And you can't wish it to be faster than it is. You've got to be honest to it."

He recalls a moment in his career when he witnessed fellow writers not reading the room well, and it led to a teachable moment in comedy.

"I was in one writer's room, many, many years ago—almost a lifetime ago—where there were one or two writers who would say a joke and then they would laugh and be like 'I think that's good enough to air.' And I'd say 'I don't think this is gearing to the idea of us looking at each other and making each other laugh.' That is such an important part of the process."

Phonte's sensibility melds perfectly with Diallo and Bashir's; and is a perfect example of the show's collaborative spirit. For the famed musician whose body of work (as a solo artist, and with groups like Little Brother and Foreign Exchange), stands as a testament to being unafraid to try things, there's a creative standard to which he holds these songs. Even if they're designed to make you laugh.

"When I'm making music, whether it's for Sherman's..., whether it's for me, whatever—I want the shit to be jammin,'" he says. "The thing with Sherman's..., the rule that I had going in, when me and Zo! are working on stuff, our North Star is 'it's not good because it's funny, it's funny because it's good.' The joke is the joke, but even beyond the joke, the songs have to jam like real songs. When talking with Diallo and Bashir, I'm just so thankful that they allow me the space and the freedom to go there. A song like 'Drop It Low For Jesus,' you could easily play that for laughs and make it really silly or whatever, but if you make it a real song...people are like 'waitaminute—what am I dancing to?!'"

The cast that Riddle and Salahuddin brought together for Sherman's... features actors, comedians and friends they've collaborated with for years. Performers like Nefetari Spencer, Will Myles, Tiffany Daniels and Devere Rogers all shine in the talented ensemble, and that's the way that the creators prefer it.

"We don't need to get the big joke," Salahuddin says. "We have episodes of our shows where somebody who doesn't look like us is doing the lion's share of the funny because we're laughing at that person, we're rooting for that person, we want that person to shine. I'm thinking specifically of Rob Haze on Sherman's Showcase. He's a writer on our show."

"He has a character this season that's loosely based on Future, and I will say, it is my favorite character of the whole season," he adds with a laugh. "It just was something I'd never seen before, and it's so funny. I'm from the Southside of Chicago, I love ignorant shit."

Both Sherman's... and South Side debuted in July 2019, with the latter landing on Comedy Central before moving to its current home on HBO Max. Networks and Black sketch comedy have an up-and-down history: FOX's 1990s staple In Living Color was groundbreaking, but ultimately fell apart after creator Keenan Ivory Wayans departed the hit show amidst bad blood with the network; the famed Chappelle's Show only lasted 2 1/2 seasons before superstar Dave Chappelle also famously chafed under network discomfort. Riddle and Salahuddin believe they've found a workable formula, but acknowledge that it hasn't been easy to find platforms that "get" their humor.

"I would argue that's been our challenge our entire careers. Being like 'We know this is funny!'; there are just gatekeepers that won't let us get it out to our people, and we don't necessarily just want to give it out for free on YouTube or something like that. At the time that we were coming up, if you put something on YouTube, it was like throwing it into the ocean."

"There's an extra level of vocation that you have to prepare yourself for. How do I get this past the filter, and it's always very difficult."

For Riddle, this is an opportunity to build a lasting legacy in entertainment. Their production company J30 Studios was formed in 2021, and under their multi-year overall production deal with Warner Bros., the brand will be creating TV projects in comedy, drama, animation and limited-run series.

"If anything, we're in here for the long haul," says Riddle. "The same way that you'll see several shows come out from Issa [Rae], and several shows come out from Aaron Spelling and Dick Wolf—we kind of wanna do that, but from the Diallo and Bashir sensibility school. Donald Glover is gonna do his shows and Tyler Perry is gonna do his shows—I love the fact that there are so many Black people developing shows now that represent them. Without admitting that we are quirky, as different as a show like Sherman's Showcase is from South Side, you can kinda understand that both of those are, in their own way, Diallo and Bashir-type shows."