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‘Insecure’ Review: Season 5 Stays True to Itself in an Enriching, Intimate Final Year

HBO's acclaimed sitcom comes to an end in Season 5, with creator and star Issa Rae making the best of her sitcom structure.

Insecure Season 5 HBO Issa Rae

Issa Rae in “Insecure”

Glen Wilson / HBO

Across its five seasons, Issa Rae’s shrewd sitcom about the millennial goose chase for love and success against the backdrop of LA’s indifference has gradually moved in the direction of urban fantasy. Paychecks stay the same, but the clothes grow more sumptuous. Apartments sprout accent walls and lamps from West Elm. “Insecure” has always afforded its characters hefty insulation from the real world, but its newest season, filmed earlier this year, feels set in an alternate universe where people never stopped going out to eat and putting on real pants. How you respond to “Insecure” Season 5 compared to Season 4 will correlate with how you’ve welcomed the series’ subtle key change. The more in love you are with its well-worn circle of friends, the more relieved you’ll be to discover that nothing, not even a pandemic, can infiltrate their deliberately constrained world. I, for one, was delighted.

When “Insecure” premiered on HBO in 2016, it was the only show on TV created by and starring a Black woman. (Well, the only show created by and starring the same Black woman — Ava DuVernay’s “Queen Sugar” premiered a month earlier with Rutina Wesley and Dawn-Lyen Gardner, among its all-Black cast.) Based on her award-winning web series, Rae devised a chummy, sharp comedy about “regular Black people living life” in the California sunshine. Race is far from incidental (“Insecure” conspicuously highlights LA’s historically Black neighborhoods, for example), but it’s never been the show’s deep well of conflict. The problems of Issa Dee, played by Rae, are as boring as they are visceral. Regular life is an argument with your friend that stems from a slight so specific you’d be embarrassed to explain it to a stranger. Regular life is not knowing what to say next and regretting what you said last. “Are we going to be OK?” Issa’s best friend, Molly (Yvonne Orji), asks her early on in the series’ final season. “You talking about the world or you talking about us?” Issa responds, though the answer is obvious. “Insecure” is at its most indelible when walking the emotional warren of its female friendships.

Insecure Season 5 HBO Issa Rae Natasha Rothwell Stanford

“Insecure”

Raymond Liu / HBO

Which is why Issa, Kelli, Tiffany, and Molly’s 10-year Stanford reunion makes a rich setting for Sunday’s premiere. Season 4 was factious, especially between Molly and Issa, but here they roam the palm tree dotted Palo Alto campus and let reminiscing wash it all away. It’s a mode of reconciliation as cheap as it is honest, but this is how long friendships sometimes persist: not by working through every issue, but by mutually avoiding the tripwires.

The conflict on “Insecure” isn’t novel — impostor syndrome, friendships strained by jealousy and neglect, the bruising search for love. But the series has long excelled at braiding together what other shows merely stack. In the Season 1 pilot as in the Season 5 premiere, career frustration elliptically compels a reckoning in Issa’s love life. And how things are going for Molly on the dating apps can affect her patience for Issa. Occasionally, the show’s conflict escalates past the point of sitcom to soap opera, like Condola’s unexpected pregnancy, but mostly what’s hard about life is the accretion of small disappointments. How high the stakes feel depends on which dyads you’re rooting for most: Tiff and Kelli, Issa and Molly; Issa and Nathan, or Lawrence and Issa.

The four episodes of Season 5 that screened for critics made for discontinuous viewing; there are jumps in time and geography and perspective that belie how far some of the characters have drifted. New faces are scarce, though a beefed up role for Issa’s intern-turned-employee Quoia, played by Courtney Taylor, is a hilariously welcome exception. It never thrills like a series racing toward crescendo, but that’s OK. “Insecure” has always fit the mold of a sitcom rather than subverted it. There’s a gratifying rhythm to its recurring shot-list: beautiful food, vibrant murals, Issa in the mirror. The finite dynamics of the same half-dozen characters falling in and out with each other deepens storylines even as it limits them.

“If you knew the end was coming, how would you make the most of your time left?” Kelli asks in the premiere episode, winkingly. In Season 5, “Insecure” leans into its legacy for awkward small talk in place of punch lines and tensions that roil between the lines of every text message. Its charismatic characters progress, inch by inch, in pursuit of grand romantic love and career clout while taking for granted what’s already aspirational about their lives: to be entrenched with people who you know so well. And to be doing it all in Lotusland.

Rae’s desire to show off her hometown is as well-documented as her desire to stay mired in regular life. “Insecure” captures something of what the long, strange stretch of an LA day feels like. How you can leave for the beach at noon and Uber from place to place to place until suddenly you’re in the Hollywood Hills in a bathing suit at 10PM, 15 miles and, somehow, an hour from home.

Sitcoms, with their reliance on tropes and archetypes, generally can’t support much personal growth for their protagonists. Who would Issa be without her pep talks? What would the show be about if Molly actually let things go? “Insecure” has been careful not to romanticize its leads’ insecurities even as it feeds on them. Self-improvement is the imaginary line that recedes as you approach it. But now that “Insecure” is ending there’s narrative space to let these women make meaningful change. Personally, I hope they don’t take it, at least not very far. I want to imagine Molly and Issa as I’ve always loved them: flawed and messy, loving and ambitious, in expensive restaurants and exquisite clothes, irrevocably knitted together in imperfect friendship.

Grade: A

“Insecure” Season 5 premieres Sunday, October 24 at 10 p.m. ET on HBO.

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