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

Issa Rae in Insecure.
(Image credit: HBO)

We are down to the final few episodes of Insecure, the Issa Rae created HBO comedy  that has run for five seasons. 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 ‘Insecure’ season 5 on?

Insecure’s final season airs on HBO on Sundays at 10 p.m. ET/PT. The series finale is set to premiere on Dec. 26.

In addition to the finale episodes, a documentary on Insecure, Insecure: The End, will premiere on HBO Max on Dec. 26 and then will air on HBO Monday, Dec. 27, at 10 p.m. ET/PT.

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. 

Also, here is the trailer for the documentary, Insecure: The End.

Are there 'Insecure' season 5 reviews?

Ahead of its premiere on Oct. 24, reviews for Insecure's fifth and final season started to come in. Variety in its review calls where the final 10 episodes seem to be heading as gratifying, if at the same time a little disappointing that some of the elements that helped make the show work so well have to be eschewed as a result of Issa's natural and earned growth. Though The Hollywood Reporter found the show to continue to "move with its signature confidence and aesthetic elegance."

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 DC-based entertainment and assistant managing editor for What to Watch, who has previously written about the TV and movies with TV Technology, Awards Circuit and regional publications. Spending most of his time watching new movies at the theater or classics on TCM, some of Michael's favorite movies include Casablanca, Moulin Rouge!, Silence of the Lambs, Children of Men, One Flew Over the Cuckoos Nest and Star Wars. On the TV side he enjoys Only Murders in the Building, Yellowstone, The Boys, Game of Thrones and is always up for a Seinfeld rerun. Follow on Letterboxd.