New season of Issa Rae’s ‘Insecure’ feels trapped on a merry-go-round

After a long hiatus, Insecure is finally back for its fourth season. But this time, not only do the characters have problems, the show does, too.

The issues are neatly summarized by an episode from the second season of another HBO comedy: Sex and the City. During brunch, Miranda (Cynthia Nixon) stages a one-woman protest and storms out on her friends. The reason? Their conversations are all focused on one subject.

“How does it happen that four smart women have nothing to talk about but boyfriends? It’s like seventh grade but with bank accounts,” Miranda says in Take Me Out to the Ball Game. “What about us? What we think, we feel, we know — Christ! Does it always have to be about them? Just give me a call when you’re ready to talk about something besides men.”

Though season four is ostensibly about the deepening rift between Molly (Yvonne Orji) and Issa (Issa Rae), it’s men who are at the heart of their constant sniping. Issa’s convinced that Molly is continually sabotaging her own happiness, this time with Andrew (Alexander Hodge). And Molly keeps anticipating that Issa will make a terrible choice to blow up her own life — again — by making another bad decision about Lawrence (Jay Ellis).

Meanwhile, Issa’s become fast friends with Condola (Christina Elmore), the public relations professional she met at Tiffany’s (Amanda Seales) baby shower. Condola is instrumental in helping Issa execute the Inglewood, California, block party she’s organizing to support black businesses. She’s also dating Lawrence.

I’ve seen the first five episodes of season four, and the show, instead of broadening its scope or deepening its exploration of existing relationships, has become repetitive, relitigating the same triangulated conflicts between Issa, Molly and whichever man happens to be in the third corner. At the same time, Tiffany and Kelli (Natasha Rothwell) are too thinly drawn. Tiffany might have a touch of postpartum depression, but it’s unclear, and Kelli’s personality consists entirely of trying to get laid.

There are plenty of possibilities to mine with two women struggling to maintain a longtime best friendship, especially as Issa and Molly drift apart and each phone call or text becomes more awkward and labored. There’s simply not enough in the show to bolster it. Without the assortment of socially maladroit weirdos who populated Issa’s former job at We Got Y’all, Rae and Orji are left to do more of the heavy lifting. Paradoxically, what they’re lifting is largely skeletal. Scenarios such as Molly’s running feud with an associate at her law firm, or the gentrification occurring in Inglewood that spurred Issa to organize the block party in the first place, both need further development. Season four feels as though it came out of a writers room struggling to push beyond what the show established in the three previous seasons. Someone also needs to be brave enough to ax Lawrence for good. As a character, he’s just not interesting enough to merit the continual will-they-or-won’t-they merry-go-round he and Issa keep riding.

Shows get into ruts. It happens. And when it does, it’s worth taking a chance or two, whether it be by rounding out supporting characters or introducing the challenge of a bottle episode. One of my favorite current examples of the former is episode five of the FX comedy Dave, which segues from the main plotline about a Jewish YouTube rapper to focus on his hype man, Gata, who has bipolar disorder. Insecure could easily do this — an arc dedicated to Kelli would pay dividends for the show, and the underused Rothwell certainly possesses the chops.

Perhaps Insecure is suffering from the divided attention of its principals. The success of Insecure’s previous seasons has resulted in a bumper crop of opportunities for Rae, executive producer and director Melina Matsoukas and showrunner Prentice Penny. Matsoukas made her feature film directorial debut with Queen & Slim. Penny did the same with the Netflix film Uncorked, about a Memphis, Tennessee, man struggling between his duty to one day take over his father’s barbecue restaurant and his desire to become a master sommelier. Rae starred opposite LaKeith Stanfield in The Photograph, co-starred with Regina Hall and Marsai Martin in Little and stars with Kumail Nanjiani in the upcoming comedy The Lovebirds, which is scheduled for release on Netflix later this year after its theatrical release was thwarted by the COVID-19 pandemic.

If Rae, Penny and Matsoukas want to maintain their audience, especially one that isn’t held captive by stay-at-home orders, it’s time to trust that viewers will follow them down a rabbit hole or two. Better to experiment now, before the scenery on the merry-go-round becomes boring.