‘Insecure’ Season 3 Review: Issa’s Pain Is Our Gain

In the HBO comedy’s return, creator Issa Rae’s heroine is struggling more than ever — but the show has hit its stride

TV series protagonists generally get smarter and better at what they do the longer they’re around. Not Issa Dee, the alter ego of Insecure co-creator and star Issa Rae. The HBO comedy introduced Issa two years ago as a woman uncertain of what she wanted out of both her work and personal life. If anything, she’s slid backwards since then.

As the third season begins, Issa is effectively homeless and crashing with old friend and sometime lover Daniel (Y’lan Noel). She’s been demoted at her job and seems more exhausted than ever at being the one black person working at a non-profit focusing on inner city schools, and by the oblivious, patronizing attitudes of so many of her co-workers. Her credit score is an embarrassment and her attempt to raise rent money as a Lyft driver mostly results in bad things happening in and to the back seat of her car. She and best friend Molly (Yvonne Orji) are getting on well after some ugliness earlier in the series, but Molly also seems to be moving in reverse, shifting to an all-black law firm in hopes of finally feeling valued, only to feel even less comfortable there than at her old place.

But if the characters on Insecure can never quite translate their desires into reality, the show sure can. The first four episodes of Season Three (it premieres Sunday) are more relaxed and confident than anything it’s done to date, and it already felt like one of TV’s most self-assured hangouts.

As Issa, Molly and Daniel (whose own career as a music producer is hitting a wall) find their lives ranging from disappointing to outright mortifying, Insecure feels as comfortable and rejuvenating as slipping into a warm bath. Rae (who wrote the season premiere), showrunner Prentice Penny (who directed it) and the rest of the creative team have complete command of the tone, the look and the language(*) of Issa’s world. That feeling — of being in the hands of talented people who know exactly what their show is — is palpable (and rarer than it should be in the prestige TV world).

(*) Early episodes of the series made a bigger deal of Issa and Molly having to code-switch as they moved from predominantly white workplaces to predominantly black personal lives. At this point, it’s an understood fact of their lives. But it’s still clear that the version of herself that Issa presents to her superficially woke colleagues at We Got Y’All is a well-studied performance that she’s increasingly tired of maintaining.

The show has always been modest in scope and knows how to track the subtle gradations in each character’s life and relationships to make those small moments feel as big to us as they do to Issa and friends. Issa and Daniel, for instance, are already fraught with shared history, and there are a lot of subtle yet clearly complicated shades to how they negotiate sharing an apartment while he’s dating someone else. Rae and company also favor long, relatively plot-free stretches where we’re simply at the club with Issa and Daniel, or following Issa as she conducts an impromptu walking tour of her old neighborhood for a handsome stranger. Issa’s such a well-drawn character at this point that she doesn’t have to be doing much for it to be appealing(*).

(*) It’s here that I confess to finding Molly-centric stories less exciting. She’s a great foil for Issa — Insecure is most lively comically when the two are together — but her own self-destructive tendencies feel more predictable. This feels relatable — we occasionally see her talking to a therapist who looks ready to cry over how hard it is to get Molly to hear the same basic advice — even as it’s trickier to pull off dramatically.

Even when moments get bigger, they’re tethered to the low-key realities of Issa’s life. The night out at the club is disrupted by a violent act, but it’s used less a shock than an excuse for Issa and Daniel to reassess who they are and how they came to this underwhelming point. Insecure has prepped us for this moment of self-examination by carefully and vibrantly following each small step these two took to get there. It’s the kind of scene Issa Rae and friends have become increasingly great at, even as Issa Dee only occasionally knows what she’s doing.