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With Insecure, Issa Rae Broke Down Doors for Black Creatives—And She’s Keeping Them Open

In the world of creative storytelling, Issa Rae is an icon. Over the last five years, she’s catapulted her Awkward Black Girl image to prominence and created a home for herself among Hollywood’s heavyweights. In Insecure’s final season, the evidence of that growth is clear. And with the multihyphenate stepping into a new chapter, so are the characters fans have come to adore.

Issa Dee and her circle of friends are no longer the insecure men and women we met in season one. They’re now parents, business owners—successful in their careers and navigating a world that requires their presence. But above all else, they are working their hardest to find themselves in a good space, shedding the relationships and preconceived notions that kept them bound to emerge their authentic selves.  

For Rae, this is the perfect note to end on. She’s not necessarily saying goodbye to the Insecure world she’s created, simply moving on. Skillfully crafting this coming-of-age story as she has lived it has been a gift, but she tells Glamour that its reception has been the greatest reward. The success of this show has allowed her to magnify other creatives and create a universe of Black talent that was previously undiscovered. 

“That was the mission,” Rae says. “Because I think when there are more of us—one, it is more fun. But also, the richness of stories as well, as a fan, is just absolutely a good feeling for me. I get to work with people I’m a fan of. By leaving the door open, it allows us more opportunities for everyone to win.” 

Rae knows what it’s like to be a creative who wants to be given a chance; she remembers those times when an HBO deal was a vision board fixture. “I didn’t know I would kill it, but I just needed an opportunity,” she says. Fast-forward five years, and Rae has killed it. Sunday nights will feel different once the last episode of Insecure airs, but Rae is confident the show will stand the test of time. She spoke to Glamour about what she’ll miss the most, her anxieties going into the show’s final chapter, and more. Read on. 

Glamour: You have been with this character, Issa Dee, for a very long time. What does it feel like to say goodbye to her?

Issa Rae: I don’t even feel like I’m saying goodbye to her because she is so much of me, and especially in the last season, we merged. But I am going to be sad to say goodbye to the other characters and her friendships with these characters and this specific world of Insecure in L.A.

This season the cast is grown, with serious responsibilities and having very real conversations. Why was it important for you to make sure you showed the full progression of these characters this season?

That was the journey of the series—a journey from insecurity to security and watching these characters grow up and come of age during a different phase of their lives. When we think about coming-of-age stories, we often think about youth—the fall from innocence. And I think there are so many different phases of coming of age. This particular journey into our 30s was something that was interesting to explore while I was going through it. 

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