Issa Rae Finds Her Voice In The Promising New HBO Comedy ‘Insecure’

Midway through the debut episode of the new HBO comedy Insecure, the show’s heroine Issa Dee (played by co-creator Issa Rae) stands in front of her bathroom mirror, prepping for a night out with best friend Molly (Yvonne Orji), trying on different shades of lipstick, and affecting a new personality to go with each one: Valley girl, tough girl, seductive white woman, etc.

This isn’t an unusual moment for either Issa, who often feels most comfortable with her own reflection, or Insecure, which at its core is about the ways that a college-educated young black woman like Issa is constantly being forced to adopt new roles depending on the situation and people around her. As she moves from her job at an educational non-profit called We Got Y’All where most of her co-workers are smugly oblivious white people, to interacting with the inner-city school kids We Got Y’All allegedly helps, to life at home with unemployed boyfriend Lawrence (Jay Ellis), to get-togethers with sorority sisters, to flirting with her record producer friend Daniel (Y’lan Daniel), Issa is in a near-constant state of code-switching, often saving what she truly feels — and the tone and language in which she wants to express herself — until she’s alone with that mirror. She never quite fits in anywhere — a school kid asks, “Why you talk like a white girl?,” her co-workers view her as a walking Urban Dictionary (or else try to act woker-than-thou and quote Kenyan proverbs at her) — except with Molly, and even Molly often loses patience with her friend’s inability to decide exactly who she wants to be — and whom she wants to be with.

But if Issa Dee struggles to properly express herself to the people around her, Issa Rae — a former web comedy star who teamed with Larry Wilmore to create Insecure — has it pretty much nailed. The show (which premieres Sunday night at 10:30, though the first episode is already available digitally and On Demand) still needs some help graduating out of the Comedy In Theory subgenre, but it displays instant command of its own voice, and tone, and feel for who the fictionalized Issa is and how to make her most appealing.

The series (I’ve seen the first six episodes) is a dry mix of social commentary and relationship dramedy. Issa is torn between Lawrence, a good guy who’s been trapped in an unemployed rut since his app failed to materialize, and Daniel, a high school pal who’s long been the one who got away, and the show smartly lets both men be plausible romantic interests, suggesting different routes Issa might want to travel in life. Molly, a successful third-year associate at a posh Los Angeles law firm, begins the series in the midst of a long sexual dry spell — the comic highlight of the premiere is Issa and Molly discussing the diminished state of a key piece of Molly’s anatomy — and though she and her friends like to complain that black women with degrees have a harder time landing men, more often than not she tends to sabotage herself by pushing too far too fast, or holding potential boyfriends to the same impossible standards she decries when she’s on the receiving end. (At times, she can be even worse than the men in that way; a later episode deals with the double-standard where a woman who once did something sexual with another woman is viewed as just experimenting, while any man who fooled around with a man even one time must be gay.)

If the romantic misadventures provide the familiar narrative hook, the sociology, and how well-drawn both Issa and Molly are as characters, is what makes Insecure stand out. Though a few of Issa’s co-workers come across as caricatures, the show is less interested in exploring them than in showing the ways in which Issa struggles to succeed in a job where she should be a natural, or in giving us Molly’s conflicted reaction to a new associate at the firm who has no interest in code-switching to appease the white partners. (Issa suggests that Molly is like the Will Smith of corporate law — equally beloved by white and black people — but that status obviously wears on her; when an internet date with another black attorney seems to be going awry, Molly finds common ground with the guy by talking about how often they’re asked to play “the black translator.”)

Insecure is less inherently dramatic than some of the other Comedies In Theory, which makes the infrequency of laugh-out-loud moments a bigger issue than on, say, Casual, but Rae is a really engaging writer and performer, and the series is charming and compulsively watchable.

Issa Dee has very little figured out at this stage, at one point lamenting, “How different would my life be if I actually went after what I wanted?” Issa Rae has already done that in her career, and the results so far are very promising.

Alan Sepinwall may be reached at sepinwall@hitfix.com