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‘Insecure’ season 5: Trailer, release date and everything we know about the Issa Rae HBO comedy

Issa Rae in Insecure.
(Image credit: HBO)

The broadcast TV networks took care of most of their fall season premieres in the last two weeks of September (with some exceptions), but it seems like HBO is claiming October 2021 as its premiere month. We already knew that we were getting Succession season 3 and the return of Larry David in Curb Your Enthusiasm, but October will also bring the fifth and final season of the Issa Rae-led comedy series Insecure.

In addition to starring, Rae created Insecure along with Larry Wilmore (she’s also an executive producer). The Emmy-winning series was last on HBO in June 2020, so the more than year-long wait for its return is sure to be welcomed by its fans.

Here is everything you need to know about Insecure season 5.

What is the plot of ‘Insecure’?

Throughout the first four seasons of Insecure, audiences have followed Issa Dee, who struggles to navigate the tricky professional and personal terrain as a modern-day African-American woman living in Los Angeles.

One of the main plot points of Insecure season 4 was the fractured relationship between Issa and her best friend Molly. The two remove each other from their lives about halfway through the season, but ultimately reconcile in the finale. However, that doesn’t mean that everything is back to normal.

While no plot information is available on season 5 just yet, the trailer released by HBO shows that Issa and Molly are still trying to figure out how to keep their newly reformed friendship from breaking again. Beyond that, love, both personal and in a romantic sense, will certainly be a part of the storyline for the main characters.

Who is in the ‘Insecure’ cast?

Insecure has been the breakout role for Issa Rae, who plays Issa Dee in the series. Rae has been nominated twice by the Emmys for her performance in the show, while it has also seen her land movie roles with the likes of Lovebirds, The Photograph and Little.

Molly is the second most important character on Insecure behind Issa, and she is played by Yvonne Orji. She has also been nominated for an Emmy for the show (Outstanding Supporting Actress in a Comedy) and recently starred in the Hulu original movie Vacation Friends.

Other recurring cast members include Jay Ellis as Lawrence, Natasha Rothwell as Kelli, Amanda Seales as Tiffany and Courtney Taylor as Sequoia. A full cast breakdown is available on IMDb

When is the ‘Insecure’ season 5 release date?

Insecure’s final season will debut on HBO on Oct. 24 at 10 p.m. ET. It will follow Succession, which is premiering on Oct. 17 and will then air weekly at 9 p.m. ET. Curb Your Enthusiasm will also be part of HBO’s Sunday night lineup, airing at 10:30 p.m. ET.

In addition to airing on HBO’s TV channel, Insecure will be available to stream as well via HBO Max. Of course you will need an HBO Max subscription for this (something HBO TV subscribers automatically get), which you can sign up for with either the $14.99 ad-free plan or the $9.99 ad-supported plan.

Is there an ‘Insecure’ season 5 trailer?

There is a trailer for Insecure season 5, and it starts off with another one of Issa’s mirror conversations with a version of herself, this time a younger Issa. We also see that Issa will return to her alma mater, Stanford, during the season. Take a look at the trailer below. 

How to watch ‘Insecure’

An HBO account is a must, either for the traditional TV channel or for HBO Max. With an HBO Max account, you also get access to all of the previous seasons of Insecure as well. 

HBO Max is available as either a standalone app, or can be an add-on to other services, including  HuluSling TV and YouTube TV. You can also purchase individual episodes or full seasons of HBO shows via Amazon Prime Video.

For U.K. viewers, there’s actually a potential hiccup in watching the latest season of Insecure. It’s been reported that Sky and Now TV, which had aired previous seasons of Insecure, no longer have older episodes, with viewers only able to purchase them through Amazon Prime UK, Google Play and Sky Store. It is not confirmed where Insecure season 5 episodes will be available for U.K. viewers.

Michael Balderston

Michael Balderston is a D.C.-based entertainment writer and content producer for What to Watch. He previously has written for TV Technology and Awards Circuit.