It'll unfortunately be another year before we catch up with Insecure [1]'s Issa. How come? Because real-life Issa Rae is busy with other projects these days (it's not a bad problem to have!). HBO Programming Chief Casey Bloys recently confirmed to Vulture that the fourth season of Insecure won't premiere until 2020 [2].
"Well, Issa became a big movie star! We're not the first place to deal with this, but when you're in business with very creative and talented people, there's a lot more opportunities for people to do things," Bloys explained. Rae recently starred in fantasy comedy Little [3] and has been filming The Photograph and The Lovebirds, the latter of which she produced. Bloys added, "Issa, I think, partly wanted a break to come back to it fresh."
There's another good reason for the delay: Insecure has in the past aired in late Summer. By holding off until Spring 2020, there's more time for the show to be marketed for the Emmys, which typically take place in September. Bloys said, "It wasn't exactly random that we ended up [scheduling the show] in the Spring, right before Emmys, so that the show should get the Emmy love that it has deserved."