The fifth and final season of “Insecure” begins with Issa (played by series co-creator Issa Rae) looking back: Her character chats with a college-era version of herself in the mirror, with young Issa wondering what the future will hold.
It’s a clever way to recap how far the character has come since the show began. Her conversation with herself takes place during a visit to her alma mater, Stanford, to speak on a panel of accomplished young alums. She now runs a multimedia company whose name she can never precisely remember and whose mission is connecting talented Black artists with resources. The fact of “accomplished alumnus” being a credible label for Issa — for all that she may feel, well, insecure — indicates forward momentum.
That makes the fifth season gratifying both for those who have rooted for the Issa character and for Rae, who has herself risen to a new level of stardom over the series’ run — but it also cuts off some of what made the show shine. In arriving at what had seemed to be the show’s destination, Issa faces new questions, while old ones have been discarded. Last season’s creative engine, the rift between Issa and Molly (Yvonne Orji), has been resolved, but the relationship between the two has been back-burnered now. Something has shifted, in the way relationships change, and in the way shows change their priorities. There’s time to explore this dynamic, but the early going of Season 5 suggests that Issa’s career breakthrough is the story “Insecure” was telling — which curtails how much we can explore subjects previously examined so richly and rewardingly.
It’s understandable; fans want to see Issa win, and her blooming career opens up new conflicts and contrasts. Still, the first four episodes of this final season feel strangely remote; the professional issues are a touch too procedural. We’ve watched Issa fight to get where she is, yet her work now lacks passion — a character beat, but one that means we’re spending a lot of limited remaining time on stories about which even those on-screen appear ambivalent.
Meanwhile, an episode featuring Issa’s ex, Lawrence (Jay Ellis), attempting to co-parent with his own ex-partner, Condola (Christina Elmore), makes clear the show’s adeptness at probing the complicated terrain of relationships. There’s reason to hope that the second half of the season will be a corrective — that Issa and Molly’s detente is building to an exploration of how friendships evolve, that Issa’s detachment from her work will result in a shift in focus. But right now, “Insecure” seems illustrative of how hard it can be to depict growth: A show designed to comment, hilariously and wrenchingly, on the precarious moments of one’s 20s is struggling to find ways to keep up the big and rousing emotions while depicting a period that’s more secure.
“Insecure’s” fifth season premieres on HBO on Sunday, Oct. 24, at 10 p.m. ET.