The World is Sketchy
A Conversation w/Diallo Riddle
“We go out of our way to make sure the music is real music, and the comedy is real comedy.” - Diallo Riddle
With the explosion of streaming apps, also has come an explosion of opportunities for unique creators from various backgrounds. Never before have we seen such a diversity of content and perspectives in the mediasphere. Add a pandemic that pushed most of us in the house, binge watching various content and you have the influx of new audiences to new content. One of the benefactors of this is writing and producing duo Diallo Riddle and Bashir Salahuddin, the masterminds behind Sherman’s Showcase (IFC), Southside (HBO Max) and some of the hip hop bits on Late Night with Jimmy Fallon (NBC). Sherman’s Showcase and Southside premiered before the shut downs of 2020 but if you’re like me, you didn’t discover them until you were forced to scramble for new content. Also if you're like me you were waiting for what felt like too long for the new seasons. I got to sit down with writer, producer, actor, showrunner, director, DJ, husband, dad, etc etc etc Diallo Riddle, just off the Sherman Showcase premier party, to learn more about how they joked and sang their way into the industry, and what to expect from the two shows!
The two met at Harvard of all places pursuing Pre-med and Economics degrees. To me it seems like art and entertainment is something they were always interested in. References to Oscar Micheux and other niche specific jokes made me think the creators were definitely film school students. Instead they actually had no plans of being professional artists. Bashir was on his way to be a doctor and Diallo was going to be “the funny guy on Wall Street.” Diallo jokes “we had to come out to our parents.. It’s like, hey Mom and Dad you know how you sent your kid to Harvard and you were so happy, well we want to go into the arts! And they go into their bedroom and quietly cry.” As a child of artists he never saw himself going into the arts and choosing poverty but it all worked out. They ended up moving to LA, taking some small jobs, putting together a sketch team that included then newcomers Robin Thede, Nika King and Nefatari Spencer who plays in both Southside and Sherman’s Showcase.
With both shows they have kept that same energy, giving space and opportunity to newcomers and personal family and friends. Diallo’s wife and children have been a part of the work, and many of Bashir’s family members including his sister Zuri who sang crowd favorite “Drop It Low For Jesus.”
Many of the special guests like Lil Rel, Bresha Webb and Marlon Wayans were people that they had worked with on other projects and invited to be involved. He tells a story of being in Vegas and running into a guy working at the bakery at the Walmart Supercenter who was hilarious and so he invited him to be a part of the show as a Reynard the Security Guard. If you’re a big fan of stand up comedy, many of the players will be familiar, including up and comer Rob Haze.
““We put a big emphasis on these talented young writers that the industry knows, but the public doesn’t.. We want to give them their shot.””
His advice to creators is to create good content with the good people alongside of you versus being “discovered” by the people that are already doing it. The approach to these shows has almost been just as random and hilarious as the show themselves. If you’ve watched either, you also know music is a big part of the work. Behind the scenes, legendary hip hop producer Phonte is responsible for a large percentage of the show’s music this season and “Lord EGOT” John Legend is a producer and player on the show.
Sherman’s Showcase is a spoof of shows like Soul Train and the Flip Wilson Show. It both celebrates and makes fun of (mostly) Black music and media from the last 40+ years. It’s complete with musical performances, film spoofs, classic commercial re-enactments and mock interviews. One bit in Season 1 that tripped me out were the commercials featuring Frederick Douglass, selling everything from Stacey Adams shoes to bonnets just to be revealed later he wasn’t really Frederick Douglass but a time traveler seeking to increase product sales for future stock options. I had no idea that these were directly inspired by an old AfroSheen commercial.
Diallo shares that the inspiration for the sketches are from the things that inspire them and that they like. Also in season 1, rapper Vic Mensa plays “Charade” , a quietly flamboyant multi talented music artist inspired by Prince. “He absolutely killed it. We were able to reach out to the real Morris Day, show him a clip and Morris was like, ‘oh I understand what this is’, and was able to get him to come on the show.” This was definitely one of my favorite episodes of the first season as I couldn’t believe that was Vic Mensa and how well he did.
Morris Day makes an appearance as himself, but he is also played by comedian Rob Haze in a Fresh Prince inspired series called “Day In Day Out”. We see Bresha Webb play Mary J Blige in multiple sketches as well as an Anita Baker inspired singer with an afro-futuristic ballad. Neyo joined with “Time Loop”, which won an HMMA Award for Best Original Song in a TV Series. We see references from the jazz age to contemporary hip hop. “We go out of our way to make sure the music is real music, and the comedy is real comedy.” Diallo reveals that in season 2 we even get a sketch inspired by the INFAMOUS Source Awards where they sought out to write a really offensive rap song. “What’s funny about contemporary hip hop, there’s a certain violence and triflingness in some of the music that comes out today, like some of these diss tracks… we always say Sherman should be totally offended by our rap song because, we always say, Sherman doesn't ‘get rap’, his barometer for anything cool turned off by 1988… but then we tried to write a song that would be a hip hop song that would offend Sherman and I’ll tell you, it’s really hard to write anything that really like compares to anything on the radio right now.” Real life has become so crazy that it’s really hard to do satire and sketch comedy because the lines between exaggerated humor to make a point, and real life have become somewhat blurred and almost unattainable. Diallo jokes “I hate to say it but it really did sound great on the club speakers. It’s a tricky bag to say ‘we’re going to make something so offensive, that’s going to offend people, oh people are dancing! Now we gotta make another one.”
Somehow Diallo and Bashir continue to do it. As they are also in development of two new shows, and the new season of Southside, they continue to make relatable and otherworldly content. Diallo couldn’t share too much about what to expect from Season 3 of Southside as HBO loves to make everything a moment but he was able to tell us that it will be back very soon. “We got some serious Chicago people on the show again this season, some from previous seasons, some we haven’t seen before.. It’s not a secret Chance [the Rapper] is going to come back, I don’t think it’s a secret that we shot some stuff at Lollapalooza.” Apparently some of the incidents happened at Lollapalooza with some special guests that ended up on the Shade Room so fans of the show and fans of celebrity drama alike will enjoy the reveals. “The city shows us so much love and I think people will really love this season.” Unfortunately there will only be 8 episodes instead of 10 due to how COVID impacted production. Even still Diallo is confident that fans will be more than satisfied with the final product, calling it a “full meal”. It was just announced that it would return in December!
Until then we can enjoy the first 2 seasons of Southside on HBO Max, the first season of Sherman’s Showcase on AMC+ and Hulu. The new season of Sherman’s Showcase premiered on Wednesday Oct 26th on IFC, you can catch it on the AMC+ app, and can be seen Wednesdays 10:30pm EST. I would say my favorite episode from this season so far was the live in Nigeria episode. A sketch I found hilarious was “Not Passing”. You can also get the vinyl or mp3 of the soundtrack for both seasons on Mad Decent.
After you’ve caught up, let me know which ones you love the most!
Listen to full audio interview below
