It takes years to become an overnight sensation, and no one knows this better than Diallo Riddle and Bashir Salahuddin. If you’re not familiar with these two prolific writers, actors and producers, you surely know their work, like the now ubiquitous “Slow Jam the News” and “History of Rap” segments, which they wrote for Jimmy Fallon while working on his late-night TV show.

Now the reigning Gamble & Huff of sketch comedy are the melanated minds behind Comedy Central’s irreverent South Side and IFC’s Sherman’s Showcase. Landing two popular shows on TV at the same time is no small fete, and it all started for the two Harvard grads with an online series they created back when George W. Bush had the nuclear codes called “The Message.”

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“That was the first time in our creative history where somebody just gave us money and they said, ‘Go make stuff,’” Bashir says of their fledgling show. His baritone voice, which gives life to both Sherman McDaniel and Officer Goodnight, pierces through an unfriendly cellular signal as the two drive to their next destination. The Message was produced as part of an HBO/ AOL joint venture called “This Just In” and featured skits like “Busters School of Magic Tricks,” where parents were forced to send their kids to a bootleg Hogwarts. If Harry Potter’s school had Mudbloods, Buster had Mudbloods, Crips and Latin Kings.

“We had been making our own videos for nothing and then all of a sudden this company was giving us like $1,000 a week, or a couple thousand a week to make content, and we went crazy. They expected us to make like 30 videos and we made like 75.”

That early show featured a few of their comedy peers, including Robin Thede, Wyatt Cenac and Nefetari Spencer.

“It was a great sketch show. I always say one day we’re going to pull that band together and do a one-off reunion show and probably never speak to each other again,” Diallo jokes before adding. “It’s a very special time in sketch comedy. Everybody’s doing the work in their own voice, and there’s a lot of good stuff to watch.”

Part of Diallo and Bashir’s winning formula is maintaining key relationships that allow for consistency in their work without it becoming repetitive.

“We tend to dig into family and friends for a lot of our work,” says Bashir. “You’re going to see people from The Message who are on Sherman’s Showcase, similarly with Southside; Diallo’s on it, I’m on it, my wife is on it, my brother is on it, two of my boys from high school are on it, our costume designers are on the same shows. Our director for Southside is a guy we met way back in the day when we worked on Jimmy Fallon. We met Matt Piedmont about five or six years before that. When you work with family and people that you’re close to, there’s a whole different vibe on set. It really feels less like people collecting a paycheck.”

One of their early and frequent collaborators is polymath Phonte Coleman of Little Brother. He met the comedy duo back in 2006 through Craig Bowers, “Count Craig” from Sherman. After brainstorming a Keith Sweat biopic that was a spoof of Jamie Foxx in Ray, Diallo and Bashir invited Coleman and his partner, Zo!, to work on an HBO show called Brothers in Atlanta.

“Them brothers, they been through the fire and back, bro,” says Coleman, who is a regular on Sherman as a songwriter and also appears as soul singer Jackie Redmond. “They got the HBO pilot in like 2014/2015. I had a role in the show and me and Zo! did a bunch of music. We got picked up and were like, ‘Hell, yeah!’ And then a month later it was nothing. We got picked up and cancelled.” It was a teaching moment for both Diallo and Bashir.

“We opened up a writers room and we wrote a whole season of the show and we did all that work,” Diallo recalls. “Then some of the same people who said we like you then called us and said, ‘Ah, we don’t get it.’ And then it was over. That’s what made it hurt. We had already written a whole season, and it was kind of nightmarish. We had never developed a show before. So the big takeaway was be careful who you sell your ideas to.”

“For us, we learned how to keep pushing,” Bashir adds optimistically. “But more than anything we learned to defend our ideas more strongly than anybody else could. Nobody is gonna be able to see your vision and get your baby the way you can.”

In a previous interview with BET, Diallo Riddle described South Side as his “own Springfield” referencing the popular fictional town from The Simpsons. The Chicago-based comedy about Rent-A-Center employees trying to reclaim overdue goods along with their sanity is filled with personalities inspired by real life, designed to reflect the humanity of Bashir's hometown.

Conversely, Bashir likens the sketch-based Sherman’s Showcase to more of an amusement park, with music, dance and science fiction combining to make one wild ride. Where Soul Train was the “hippest trip in America,” Sherman’s Showcase is just plain trippy.

Diallo, who is also a professional DJ, brings his curation skills to Sherman’s off-beat opinions and inside-baseball nature of sketches like “Temptations 11,” where a legion of Motown soul singers plot to rob Berry Gordy’s house for unpaid royalties.

“One of my favorite things about Sherman’s Showcase is that it feels like a conversation between Diallo and [The Roots drummer] Questlove about which drummer is James Brown’s best drummer,” says Bashir. “’Which Prince off-shoot group put the best song out? Was it The Time or Vanity 6?’ It’s in the weeds, but I think people like to watch something where they feel like their intelligence is being respected.”

And, of course, there is Sherman, the quixotic, opinionated host of this funky time-bending variety show who just wants to keep the party going.    

“It’s fun to play him because again, many actors love to inhabit a character who represents things they don’t personally believe in... He’s always wrong, over the top and really untrustworthy. But he definitely wants to have a good time.”

In its first season, Sherman’s Showcase has boasted an enviable collection of guests from John Legend and Ney-Yo to Tiffany Haddish and Quincy Jones. But one of their biggest viral moments, “Drop It Low for Jesus,” was performed by Bashir’s sister, Azuri, and written by Phonte and Zo!. It’s the kind of ridiculous juxtaposition of the carnal and religious that Kanye West has just now caught onto for his Sunday Service “remixes” of secular music.

“The comedy is accessible to anybody, but I think if you really know the background of the music, then you get an extra level of appreciation,” says Diallo. “That thing that you think is a reference to that other thing is definitely intentional.”

Sometimes the references are inspired by real time events. In one sketch Bashir plays a scooter-bound singer named Big Freddy Payne, who performs a new song called “Runnin” (“That is 100% my voice”) and the entire idea was born out of a class trip to Las Vegas.

“We took the writers to multiple Vegas shows so we could bring some of that pomp and circumstance and glitz to Sherman,” Diallo shares. “And we saw a guy named Fat Elvis. He was about 300 pounds. He needed help getting into his chair, but he was great! He sounded just like Elvis. I stared at Bashir and said, ‘What if this IS Elvis and he’s just ashamed that he’s gained weight in the last 30 or 40 years?’ We thought that was so funny that we wrote it into the show. That’s why Big Freddy Payne is pretending to not be himself, because he doesn’t want the world to know what happened to him.”

Whether it’s an overweight, scooter-bound soul singer or a sucker-punching Frederick Douglass, writing comedy comes with a lot of risk, especially in 2019. But Bashir and Diallo feel they have a formula for funny that won’t leave them on the wrong side of a Twitter mob.

“We’re in a period where you gotta be able to stand behind your work,” says Bashir. “You can’t just say something nowadays and then disappear. There are things on both shows where one or two people in the writers room will say, ‘I dunno.’ Both of our writer rooms are predominantly Black — almost all Black — and we go forward with a consensus of people [with] comedy opinions. So we feel if we can make it out of those writer rooms with approvals, then we’re happy to back up anything that comes out of it.”

With the first season wrapped, the two are hopeful for a second season and already have some ideas for what they’d like to do, including a live Las Vegas style review.

“I spoke to Phonte and I said I want to see Percy Miracles on the show,” Diallo says of Coleman’s near legendary spoof of soul legend Ron Isley. “That’s one of our big goals for season two. In addition to Percy, I’d love to do something with Anderson .Paak. I listen to his podcast. I think he’s hilarious and he also does fake songs that are really good. So we’d love to get him in Season 2, as well as Questlove, we didn’t get him this season. Snoop has reached out. So, I think Season 2 will be an amazing fete.”

While it’s pretty much a lock that Sherman will be back on IFC, if the duo is looking for a new network for their show, we have one great suggestion. 

“Sherman’s Showcase would be the number-one show on UBN,” Phonte says referencing the fictional TV network made popular on his group Little Brother’s albums. “We’d put it on right after Deyana Changed My Life.” 

Blackness!