‘Insecure’ Is Ending After Season 5, Issa Rae Confirms by Cliche Wednesday, January 13, 2021 Published 19 hours ago Insecure is concluding after season 5. Amy Gravitt, the Executive Vice President of HBO Programming, released a statement on Wednesday (January 13) praising the show while announcing the news of its ending. “Issa [Rae] has turned insecurity into an iconic form of comedy,” said Gravitt, according to Deadline. “The show is as incisive as it is heartfelt, and it has resonated strongly with its audience because of the deeply personal work that Issa, Prentice, Melina, the cast and the writers have put into it. This talented team has conceived a brilliant final season for Insecure and we look forward to having many more stories to tell with this singular group of collaborators.”