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Issa Rae Is Booked and Busy! See What's Next For Her After Insecure 4 Shares Insecure is ending after its upcoming fifth season. While it pains us to say goodbye to the show, it's definitely not the last we'll see of Issa Rae. In fact, the 36-year-old media mogul already has several projects lined up through her massive five-year deal with WarnerMedia, which is valued at $40 million. The partnership gives HBO, HBO Max, and Warner Bros. television exclusive rights to Rae's television work and a first-look film deal that spans WarnerMedia brands. "They wifed me up," Rae said to Variety about ...

HBO's 'Insecure' to end with Season 5 By (0) Issa Rae will make the fifth season of "Insecure" the show's last. File Photo by John Angelillo/UPI | License Photo Jan. 13 (UPI) -- HBO announced Wednesday that the upcoming fifth season of Insecure would be its last. HBO previously announced the Season 5 renewal in May 2020, while the fourth season was still airing. Season 5 of Insecure begins production in January and will air later in 2021 with director/executive producers Prentice Penny and Melina Matsoukas returning. Advertisement Issa Rae co-created Insecure with Larry Wilmore. In the h...