Insecure Gets a Joyous Swan Song

Five years into its run, it’s hard not to feel like the world did Insecure dirty. Issa Rae’s HBO comedy has received near-universal critical acclaim and boasts a legion of adoring fans, but since its debut in 2016, it has received just 11 Emmy nominations, and only one for Outstanding Comedy Series. No shade to Ted Lasso, but the feel-good, predominantly-white sitcom earned 20 Primetime Emmy nods for its first season. Where’s the love for Insecure, a series that has continued to innovate and raise the stakes, year in and year out?

That said, if Issa Rae and co-creator Larry Wilmore feel in any way slighted by Ted Lasso and its “heartwarming sitcom” ilk, you wouldn’t know it from Insecure Season 5, a joyous affair that serves as a fitting swan song for the series. In its final season, Insecure’s characters attempt to finally move forward in their personal and professional lives, an endeavor that the show handles with the utmost care and respect. As young, Black people living in South L.A., “moving forward” looks different for each character, but Insecure never fails to find humor in the everyday situations that lead to their larger journeys of self-discovery.

Insecure’s remarkable ability to walk the fine line between absurdity and reality is on full display in Sunday's Season 5 premiere, which sees Issa (Rae), Molly (Yvonne Orji), Kelli (Natasha Rothwell), Tiffany (Amanda Seales), and Derek (Wade Allain-Marcus) travel to Stanford University for their ten-year college reunion. While Issa and Molly took small steps to repair their rift at the end last season — their beef formed the backbone of Season 4 — they still remain on rocky footing two months later, and they’re hesitant to spend an entire weekend tip-toeing around their issues.

Meanwhile, Issa, fresh off the success of her block party, is asked to participate in a panel for alumni entrepreneurs, but she finds herself dealing with a serious case of imposter syndrome. Is she truly on the right path, or has she spent the past year on a fruitless endeavor? What does “growth” really mean, and how its it measured? Insecure has never been afraid to ask big questions, and Rae and Wilmore do so more quickly and more confidently than ever in the premiere, as if to say, “This is who we are, and what we’ll be dealing with this season. Either you’re in or you’re out.”

Intertwined with all this heaviness is the first great Kelli-ism of 2021. Due to a clerical error, Kelli has been written off as dead by the Stanford Alumni Association, and the mistake triggers something of an existential crisis for our favorite horndog accountant. Kelli’s reaction is (unsurprisingly) wholly ridiculous, but it also gives Rothwell, ever the scene-stealer, a chance to mine her character’s more serious side. Yes, everyone on Insecure is glowing up and growing up, including Kelli, who embraces her inner goop (but without the Gwyneth Paltrow toxicity) over the course of Season 5.

While last season reasserted that Issa and Molly’s friendship is Insecure’s main focus, their romances remain a major subplot. Without divulging any spoilers, Issa’s self-reflection extends to her relationship with Lawrence (Jay Ellis), particularly in the wake of Condola’s (Christina Elmore) pregnancy bombshell. Meanwhile, Molly is ready to get back into the game after her breakup with Andrew (Alexander Hodge), but first she'll need to address the hangups that have led her to push away great guys in the past.

It should go without saying that Insecure’s final season is every bit as funny, well-soundtracked, and vibrant as seasons prior (the standout Episode 4 features a beachside party set to Renni Rucci’s “Show Me Something”), but it may also be the comedy’s most unapologetically joyful outing. After years of internal and external pressure, Issa, Molly & Co. can finally just be. Feeling comfortable in your own skin is perhaps the greatest benefit of maturity, and it’s one Insecure has come by honestly, through its many big swings and messy entanglements. How’s that for heartwarming?

Insecure's fifth and final season premieres Sunday, October 24 at 10:00 PM ET on HBO.

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Claire Spellberg Lustig is the Senior Editor at Primetimer and a scholar of The View. Follow her on Twitter at @c_spellberg.