Everything We Know About 'Insecure' Season 5

The Issa Rae comedy is coming back for one final season.

Yvonne Orji and Issa Rae | Merie W. Wallace/HBO
Yvonne Orji and Issa Rae | Merie W. Wallace/HBO

It was just back in 2016 that 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. 

While Season 4 saw Issa and her BFF Molly (Yvonne Orji) trying to "level-up" in their personal lives, it seems like the two still have a long way to go on their own, and as a duo. Considering the season finale seemingly left many things unsaid and dropped a handful of bombshells, it's definitely fair to start looking toward the next installment to see how everything gets patched up. While we'll have to kill time with some mirror raps of our own as we wait for more of Issa's, here's everything we know about Season 5 of Insecure so far. 

Will there be a Season 5 of Insecure

Insecure is definitely coming back for a fifth season. The renewal was confirmed before Season 4 was even over, back in May 2020, as reported by Deadline. They shared that showrunners "Issa Rae, Prentice [Penny], and the whole Insecure team will be getting back together," so it should be another round of laughs and tears as usual. 

A bit of freaking out is in order, though: Season 5 will be the final season of Insecure. Variety reported in January 2021 that the show was coming to an end. It doesn't sound like the series was canceled, but rather the showrunners decided it was time to wrap things up appropriately, as executive vice president of HBO Programming Amy Gravitt told Variety "this talented team has conceived a brilliant final season." At least we'll be getting to say our goodbyes to Issa, Molly, and co. as the show intended.

Plus, it won't be long till we get the next comedy project from Rae: HBO announced that she'll be starring in and writing a new eight-episode, half-hour series called Rap Sh*t, about two erstwhile high school friends teaming up to form a rap group in Miami. Syreeta Singleton, who has written for InsecureCentral Park, and Black Monday, will be the showrunner.

When will Insecure Season 5 premiere? 

Issa Rae shared on social media that filming began in late January 2021 with the tweet, "First day of Season Bye-ve." (Okay, sad). Then, in late February she posted that filming was still underway and appeared to be going well—so if the series isn't done shooting yet, it should be wrapping up soon. Since Insecure isn't one of HBO's heavy lift productions, it seems likely that the post-production process should fly by, hopefully making for new episodes sometime this summer/early fall. Regardless, HBO has confirmed the upcoming, final episodes will hit the air sometime this year, so the wait shouldn't be too much longer now.

condola insecure
Jay Ellis and Christina Ellmore | Merie W. Wallace/HBO

Who in the cast is returning?

Insecure wouldn't be the same without its core cast, so all of the main leads will be back. Issa Rae will reprise her role as Issa Dee, Yvonne Orji will return 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. And although nothing's confirmed, it seems like Condola (Christina Elmore) will 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. 

How many episodes are in Insecure Season 5?

While an official episode count hasn't been announced, Rae mentioned to People that there will be "more than eight episodes" in the final season. That's how many Seasons 1-3 went with, and then Season 4 was upped to 10 installments, so it seems as though that's what things are looking at for the final go of the series. 

insecure issa rae jay ellis
Issa Rae and Jay Ellis | Merie W. Wallace/HBO

What will Season 5 be about? 

According to showrunner Prentice Penny, the final season hinges on one question: "If life doesn't look like how you imagined it, does that mean it's a success or a failure?" He spoke to Entertainment Weekly about what that means and how it should carry into Season 5, and it builds upon just about every one of the developments from that jaw-dropping finale. 

While Issa and Molly attempted to talk things out after their relationship took a hit when they each tried to focus on their own lives, their friendship isn't necessarily going to be back to normal. Penny said, "We don’t want them to go back to where they were. They’re going to be forever changed by this, forever humbled by this, and hopefully, forever close by this." He explained that the new episodes will explore what the road back to their close friendship, and ultimately the "2.0 version" of it, will look like. 

Where their relationship stands isn't the only unpredictable wrench thrown into Issa's life that'll be explored going forward. Penny explained to EW that it was intentionally left uncertain whether or not Issa and Lawrence are still an item, but now that Condola is pregnant with his child, Issa will have to reevaluate whether or not she still wants a life with him even if it's not the ideal one she imagined. Could that send her back onto the Nathan train? It's hard to say, but it'll certainly affect Lawrence individually, and whatever relationship remains between the two of them. 

On top of dealing with all that drama, Rae told Popsugar 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.

Continue to check back, as we'll continue to update this post as more information regarding what's up with our favorite L.A. friends is announced.

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Sadie Bell is the entertainment editorial assistant at Thrillist. She's on Twitter at @mssadiebell.
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