This Will Probably Be The Last New ‘Insecure’ Trailer You’ll Ever See

The fifth and final season of Insecure will premiere on October 24th.

Issa Rae’s groundbreaking TV show Insecure is coming to an end. Season 5, which will premiere on HBO and HBO Max on October 24th, will see Issa, Molly, Lawrence, and more wrap up their respective journeys. 

HBO has just released a new trailer for the show. In it we see Issa admiring how far she’s come along since season 1. But, she is also acknowledging that she’s at a crossroads, with her relationship with Lawrence and Molly very much still in flux. 

Earlier this year, Issa announced that Insecure was coming to an end. 

“We always planned to tell this story through five seasons,” Issa told Deadline. “But we couldn’t have made it without the tremendous support of our audience.”

Issa Rae and Insecure showrunner Prentice Penny based the comedy off of Rae’s Awkward Black Girl YouTube sketches. In 2020, the show earned eight Primetime Emmy Award nominations for its fourth season. For her portrayal of the show’s protagonist, Issa, Rae earned two Golden Globe Award nominations in 2017 and 2018: one each year for Best Actress in a Television Series, Musical, or Comedy.

Although Insecure is coming to an end, Issa’s relationship with HBO is continuing to blossom. In March, it was announced that Rae inked a new five-year overall deal with HBO. The deal is worth a reported $40 million and Issa’s media company, Hoorae, has numerous cool shows in the works, including Rap Sh*t and The Vanishing Half.

Check out the latest Insecure trailer below.

Dimas Sanfiorenzo

Dimas Sanfiorenzo is the Managing Editor for Okayplayer. He specializes in coverage centered around music, pop culture, and politics. Email:

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Dimas Sanfiorenzo

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