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A Writer So Nice They Gave Him A Show Twice – An Interview with Diallo Riddle

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Chicago, USA; home of The Windy City, deep dish pizza and once The Oprah Winfrey Show. As great and unique Chicago is with its die-hard attitude, hustling mentality, jazz music and the gangsta spirit of Al Capone; over the years the media has not been too kind with its portrayal of the city.

Just when TV shows set in Chicago couldn’t get any bleaker, presidential attacks couldn’t get anymore darker or Jussie Smollett couldn’t get anymore Smolletter, it seemed the city couldn’t shake its negative reputation.

Something had to change.

Enter Diallo Riddle, named one of “Variety’s Top 10 Scribes to Watch, Diallo got his start in television as a writer on Chocolate News for Comedy Central. He went on to write and perform for Late Night with Jimmy Fallon from 2008-2012, arriving three months before the show premiered and as one of only 5 writers. Some of the stand-out segments he wrote included Slow Jam the News featuring Barack Obama, and the first three editions of A History of Rap with Fallon and Justin Timberlake.

Armed with his writing skills, his passion for music and his famous friends he set out to create shows that represent the beauty, uniqueness and hilarity that is Chicago. While most writers are lucky if they find success with one show, Diallo has two upcoming shows airing this summer that’ll make the residents of Chicago proud and viewers entertained.

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The first is the upcoming Comedy Central series South Side about a rent to own business on the south side of Chicago. South Side is an aspirational, scripted comedy set in and around the working class neighborhood of Englewood on the South Side of Chicago. The show follows two friends who just graduated community college … so now they’re ready to take over the world! But until they do they’re stuck at Rent-T-Own, a retail-rental crossroads where the South Side’s vast ensemble of characters come together. Despite the obstacles of inner-city life, these friends and their co-workers all strive to achieve their entrepreneurial dreams. Brought to life by local Chicagoans, both in front of and behind the camera, this show gives viewers an authentic portrayal of what life on the South Side is all about. It’s evidence that what you see on the news is only a small piece of the city.

The series was created by and stars Diallo and his writing partner Bashir Salahuddin (GLOW). The comedy, which was shot on location in Chicago’s Englewood neighborhood, gives an authentic look into what life on the South Side is all about.

South Side is set to premiere on July 10 on Comedy Central.

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Diallo and his writing partner also created and star in a scripted musical variety sketchy comedy, titled Sherman’s Showcase. The eight-episode series has it all: music, comedy, games, and dancing (executive produced by John Legend’s Get Lifted Film Co). Guest stars include Marlon Wayans, Tiffany Hadish, Common, Quincy Jones, and Ne-Yo, to name a few.

The series will premiere July 31 on IFC.

Diallo is truly a fascinating man, which is why The Koalition had to speak with him about his shows, his views on comedy, his failed Atlanta show and more.

Check out our interview below.

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