Everything We Know About 'Insecure' Season 5

The final season of Issa Rae's HBO comedy is coming soon.

issa rae in insecure season 5
Issa Rae in 'Insecure' Season 5 | Merie Wallace/HBO
Issa Rae in 'Insecure' Season 5 | Merie 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.

Yvonne Orji and issa rae in insecure season 4
Yvonne Orji and Issa Rae | Merie W. Wallace/HBO

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 per 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.

Luckily, 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 Insecure, Central Park, and Black Monday, will be the showrunner.

When will Insecure Season 5 premiere?

The final season is coming soon. When HBO dropped a teaser for Season 5, the network announced it was set to premiere on October 24. If you're already getting emotional about having to say goodbye to the series, you can prepare for the tears that are bound to come by checking out Rae's farewell to the show she posted on Instagram when filming wrapped in June 2021. 

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Is there a trailer for Insecure Season 5?

Yes! HBO released the first official look at the upcoming final season in early September, sharing a brief teaser. Like teaser trailers for other seasons before it, this one features another clip of Issa looking at her reflection in the mirror (including shots of her doing the same from seasons prior). Instead of another classic mirror rap, though, it takes a more somber approach as Issa says she wants to be "drama free" but is "terrified" about what's next for her. Of course, there's a playful moment at the end where she's joking with her reflection—but it looks like we're in for an emotional whirlwind of a season!

jay ellis and christina ellmore in insecure season 4
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.

It also would make sense for Condola (Christina Elmore) to stick around, given the news she dropped in the Season 4 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?

No official episode count has been announced yet, but according to IMDb, it looks like we're in for eight more installments. That's how many Seasons 1-3 went with, and then Season 4 was upped to 10 installments, so we'll take what we can get as the show wraps up everybody's stories.

issa rae and jay ellis in insecure season 4
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.

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