Issa Rae’s Insecure has been one of HBO’s biggest success stories over the last decade. Adapted, in part, from Rae’s web series Awkward Black Girl, Insecure premiered in 2016 and soon went from cult hit to network powerhouse, earning 10 Emmy nominations, with Rae, who has become one of TV’s biggest stars, garnering six. But all good things must come to an end, and so must Insecure, which wraps up this October. The fifth and final season of Insecure premieres on October 24. Those last 10 episodes now have a teaser trailer, too, featuring Issa, once again, going to war with herself.
Insecure hasn’t really suffered in terms of quality over its first four seasons. Season four, which ended in June 2020, was met with praise from critics. F0r the A.V. Club, Ashley Ray-Harris called the season four finale “daring” and “audaicous,” writing:
Insecure is asking viewers to move on too. That Prentice Penny chose to use the very fan theories that have dominated Twitter to force us to accept Issa and Lawrence’s new reality is brilliant storytelling. It’s also the perfect end to a season that gave Insecure more time and space to tell the story it wanted to tell. Even though Twitter fans called these possibilities out, they still didn’t feel like things Insecure would actually do. Penny’s script doesn’t just call our bluff, it makes sense of everything too.
By the sounds of things, Insecure has been priming fans for the ending for a while now. If the previous seasons are any indication, it’ll be a treat to see if they can stick the landing. Thankfully, Rae doesn’t have to say goodbye alone. The rest of the series regulars, including Yvonne Orji, Jay Ellis, Natasha Rothwell, Amanda Seales, and Courtney Taylor, will also be returning.