After attending Harvard University, Riddle and his writing partner Bashir Salahuddin, started a sketch comedy group called Cleo's Apartment.

The group's members included Robin Thede, Thomas Fraser, Wyatt Cenac, Nika King and Nefetari Spencer.

Riddle, alongside his creative partner Bashir Salahuddin, have launched multiple projects over the years through their production company, J30 Studios.

[1][9][10] Among his sketches on the show, Riddle co-wrote Slow Jam The News with Barack Obama and three editions of A History of Rap with Jimmy Fallon and Justin Timberlake.

[14] On May 3, 2018, it was announced that IFC picked up to series Sherman's Showcase, a scripted musical variety sketch comedy show which Riddle wrote with his writing partner Bashir Salahuddin.

[33] In 2011, Riddle was nominated for the Primetime Emmy Award for Outstanding Writing for a Variety, Music or Comedy Series through his work on Late Night.

[36] In 2022, Riddle was nominated for the NAACP Image Award for Outstanding Directing in a Comedy Series for the “Tornado” episode of South Side.