It was just back in 2016 when Issa Rae took her talents over to HBO to adapt her popular web series Awkward Black Girl into Insecure. Now, after four successful seasons and 11 Emmy nominations, the comedy has become a mainstay and the hype around it only rightfully continues to grow. Following a young Black woman in LA named Issa Dee and her (mis) adventures in professional success, friendship, and love, the series co-created by Rae and Larry Wilmore has been hailed for its relatability and earnest laughs—and has drawn seriously divided lines between fans about their eye candy of choice.
As we cry tears of joy that Issa is moving onto bigger endeavours, a collective sadness knowing we will no longer have our Sunday night LA, black owned business reppin’ relatable, realest friend (in most of our minds anyway) show. The 10-episode fourth season Emmy-nominated HBO series from Issa Rae and Larry Wilmore will be dearly missed.
Issa is a natural hair icon and the greatest bathroom mirror rapper of our time. She’s awkward, but sensible (except in matters of the heart). Despite being one of the most relatable characters, she dances to the beat of her own drum.
“I think you can expect these individual journeys,” Rae teased. “When you’re used to being friends with someone for so long, so much of your identity gets wrapped up in that,” I think that exists for relationships in general. I think both of them need to take a step back and kind of examine ‘how did we get here? And who am I without this person?’
Here's what we know about the upcoming installment of Issa Rae Insecure Season 5.
For starters I know, it’s heartbreaking .. HBO DID confirm that Issa Rae Insecure will be ending with its fifth season.
“Prentice [Penny] and I are so grateful that HBO believed in our show from the beginning and kept faith in us to see our vision through the end,” she said. “We always planned to tell this story through five seasons, but we couldn’t have made it this far without the tremendous support of our audience. I feel blessed beyond measure to bring our characters’ stories to an end, on-screen at least.”
HBO Max confirmed in a new video that Issa Rae Insecure Season 5 would be arriving in 2021. Issa also teased with a clip , it is clear the filming has begun
Issa and Molly's friendship won't be the same.
We'll have to wait and see whether Lawrence and Issa are still together.
In the final moments of the Season 4 finale—spoiler alert!—Issa and Molly finally meet up for a long-overdue sit-down, one that came after weeks of high tensions and frustrating arguments. But that doesn’t mean their broken friendship will be completely mended come next season. The writers “don’t want them to go back to where they were,” showrunner and director Prentice Penny told Entertainment Weekly about crafting Season 5.
When asked whether Issa and Lawrence’s final joint scene—after he reveals that his ex, Condola, is pregnant with his child—was supposed to be read as a breakup scene, Penny played coy. “I mean, you have to wait until season 5. Where’s the fun in that?” He also explained that that scene was intentionally vague and up for interpretation.
There could be more of Issa and Nathan.
“I think we’re trying one of the questions that’s still sort of hanging from this: The Issa-Lawrence Issa-Nathan [relationships],” Penny teased of Season 5 to EW. He added that other potential themes include whether Issa finds professional success, where her friendship with Molly stands, and whether Molly can find love.
“Really, the thing we’re playing with is, again: If life doesn’t look like how you imagined it, does that mean it’s a success or a failure?” Penny.
Who in the cast is returning?
Insecure wouldn’t be the same without its core cast, so you can assume that all of the main leads will be back. Issa Rae will reprise her role as Issa Dee, Yvonne Orji will be back as Molly, as well as Natasha Rothwell as Kelli, Jay Ellis as Lawrence, and Amanda Seales as Tiffany.
Now that Andrew (Alexander Hodge) and Molly broke up, though, it’s hard to say if we’ll be seeing any more of Asian bae. But as for Condola (Christina Elmore), it seems like she’ll definitely be sticking around, given the news she dropped in the season finale. More on that reveal below, but when you consider the detour that throws in Issa’s relationship with Lawrence, it might be time for Nathan (Kendrick Sampson) hive to shine and for that ex to be back in the picture as well. At the very least, photos caught the actor on set in a scene alongside Issa, so it’s certain he’ll appear at least a bit.
Kerry Washington is returning to direct.
Washington will be directing Insecure’s Season 5, Episode 5, which was written by Laura Kittrell. The Scandal star made the announcement in an Instagram video. The actor-director shared the news with a clip of Rae and Orji discussing the last time she directed an Insecure episode, which was for Season 4.
About Season 5
On top of dealing with all that drama, Rae told Pop-sugar that what she’s really hoping for next season is for her character to start feeling “comfortable.” She said, “I don’t think we’ve ever seen her be that…. We’ve always talked about this show as being a journey to get these characters to a place where they’re secure with their insecurities, and so that’s what I want for her, whether that’s through her man, through her passion. Whatever it is, I just want her to find her footing and be okay—and also not broke.” It’s what we want for her, too.
I’m excited to see what this final season instalment will bring to say the least. With the talent of this writing team and the potential directions they can go, alongside Issa knowing how much the fans have/are invested. I’m confident we can expect nothing but raw, witty, relatable top tier material as we’ve come to already appreciate from Ms. Issa Rae.