How Casual Complexity Built to a Gripping Emotional Arc in the First Season of Issa Rae’s ‘Insecure’


We’re pretty big fans of Issa Rae’s so-real series, Insecure. So to celebrate season 2, we’re taking a look back at the acclaimed first season, and recapping the highly anticipated new episodes. Don’t miss the return of Insecure on Sunday, July 23 at 10:30pm, only on HBO.

The penultimate episode of Insecure‘s first season builds to Hitchkock-level (it’s scary, emotionally!) tensions with the collision of everything creator/star Issa Rae’s character Issa Dee has been working towards, or self-destructively working against, throughout the season. In these first eight episodes of the series, Issa began to thrive at her work, “We Got Y’all” —the nonprofit whose logo of a giant white hand benevolently cupping three miniature silhouetted black children figures, speaks volumes to how the organization sees itself. By Episode 7, despite obstacles stemming from the cattiness and obliviousness of some of her more insufferable “altruistic” white colleagues, Issa has managed to assert herself and partially actualize her vision for a fundraiser meant both to butter up potential donors and truly honor the students. That evening, unfortunately, also becomes host to a meeting she’d hoped would never occur: that of her boyfriend, Lawrence (Jay Ellis), and the man with whom she very recently had an affair, Daniel (Y’lan Noel). After presenting us with one of the more complex female friendships television has to offer, the show has also grounded Issa’s relationship with Molly (Yvonne Orji) in enough layered history to allow them to truly tear into each other’s insecurities in the ways only best friends can. And somehow, this also happens on that emotionally boiling evening of the We Got Y’All fundraiser gala in Episode 7 (“Real as F**k.”)

And so a bold dramatic framework emerges from Insecure‘s confident nonchalance: these everyday lives, and everyday insecurities, become so comfortable and familiar that when they escalate to something as gut-wrenching as the confrontation between Issa and Lawrence — and Issa and Molly, and Issa and Daniel, for that matter — you’ll be surprised by what’s hit you. In Season 1, the nuance, discomfort, beauty, and hilarity of isolated small moments truly build to something — and the existence of that casual setup wherein we simply get to live with the characters ensures that the cheating/losing it all narrative doesn’t seem trite, but rather weighted in real stakes. Sure, this is a comedy — and a very, very funny one — but Insecure is another example of television that leaves old notions of what comedy can and can’t do, what ground comedy can and can’t cover, at the door. How did the show so effortlessly build up to the sheer rawness of its final episodes?

The series employs a tactic of casual immersion that ultimately goes quite deep: immersion into Issa, Molly, and Lawrence’s work, sex, and social lives. While many series focus disproportionately on one or the other, Insecure understands how they each bleed into one another, and gives them all equal time to develop and provide insight into the ways these characters move throughout their days. In this, it affords itself the room to meticulously examine the nuances of race and performance, delving into what’s spoken and unspoken as these characters traverse different racialized/economic planes from their time work to hanging to dating.

Molly, for example, is a corporate lawyer and the only black woman working in her office — until a new hire, a summer associate named Rashida, shows up. Rashida, as Molly perceives, doesn’t understand the necessity of code switching in order to function as a black woman within a sphere dominated by bourgeois white social expectations — and, of course, sheer racism. The show’s multilayers are on full display when Molly attempts to impose her advice for how to act less “black” on Rashida, and Rashida rightfully rebukes Molly’s wisdom-sharing as condescension and stereotyping. It becomes even more uncomfortable and disheartening when it’s also made clear that Molly’s urge wasn’t unsubstantiated: she’s worked here long enough to know what her colleagues tacitly won’t accept. Eventually, her colleague asks her to “have a talk” with Rashida, sub-textually demanding Molly act as a bridge between Rashida and their perception of acceptability tied to whiteness and class.

Issa’s work experience similarly explores the unspoken, but using a different (and more comical) tactic: often, when one of her mostly-white coworkers attempt to undermine her or override her, we see Issa speaking her mind —— but then we see what really gets said. Sometimes, in order not to be further undermined by the “angry black woman” stereotype, what really gets said is…just a shrug or a half-grimacing smile.

Things are no less complicated within Issa’s personal life — which, for much of the first season, she feels is mired by her relationship to the kind but stagnant ways of her boyfriend, Lawrence. The season begins with big hints of where it’s ultimately leading: in the first episode, she has the impulse to go to an open mic to see Daniel, her Ty Dolla Sign-producing sort-of-ex. Though nothing happens for quite a while, you’re primed to assume — correctly — that it will. That’s not the only thing that’ll come back to haunt Issa that night: there, she also freestyles “Broken Pussy,” a rap about Molly’s vagina, which we’ll later find out someone just so happened to record. Speaking of Molly’s “Broken Pussy,” Yvonne Orji’s character’s relationship to love and sex and dating is another of the more highly developed elements of the series. Largely because of the social mobility Molly’s earned professionally by setting crazy expectations for herself, her sex life is full of at-times backwards projections about class and image. How will it fit into the constricting ideals she’s imposed on herself to match those of society? How will it fit into her constricting ideals of black masculinity — and what it means for her femininity — if she dates a man who (even just once) got blown by another man?

Molly’s game-playing with Jared, who works as a salesman at Enterprise, is one of the show’s strongest examples the necessity of showing the worst sides of a character in order to make them real. First she rejects him after joining the The League, and realizing that her dating life can, with the help of an elitist app, match her professional vision of getting to the top of the hierarchy. But when she gets condescended to by a man (played by Jidenna!) she slept with — and then all too rapidly tried to sculpt a “relationship” with — from the app she suddenly wants Jared back. So, with his class no longer seeming an issue, things are looking great for Molly and Jared…until she finds out he once did sex stuff with a man, and rejects him as though a blow-job has forever tainted his ability to embody masculinity within a relationship with a woman. Molly, in the ways her insecurities are reflected in her dismissive treatment of some people who come in and out of her life, is painfully real.

These habits of Molly’s, Issa’s infidelity, and the race and class tensions of within their professional lives come to a head in the aforementioned seventh episode of the season, where both Issa and Molly and Issa and Lawrence’s relationships threaten to break irreconcilably at the fundraiser. After Lawrence has his suspicions confirmed about Issa’s one-time affair with Daniel, he leaves their apartment in a quiet fury; ultimately, in the finale, as we’re hoping — and Issa’s hoping — that Lawence will come back to her, we instead see him having explosive sex with the woman who works at the bank near his job at Best Buy. The future of their relationship is left open, though it’s hard not to feel like, at least for a while, Issa will be doomed to following Molly into the bleak world of online dating. (In fact, if you’ve seen the trailer for Season 2, you’ll know this is the case.)

The different facets of life depicted on the show are also rendered with sensorial hyper-specificity by the team, presumably particularly as overseen by Rae, co-creator Larry Wilmore, and “Formation” director Melina Matsoukas, who executive produces and directs four of the eight episodes, Raphael Saadiq (who provides original music) and Solange Knowles, who was a consultant for the series’ unparalleled soundtrack. As it crosses L.A. from the monolithic, glistening, “money”-screaming skyscrapers of downtown to the ’50s apartment complexes and bars of Englewood, Insecure pulls off something rare: something that seems so casual, that looks and sounds so attractively effortless, yet whose every moment feels weighted in humor, or emotional complexity, or social commentary — often with no separation of any of the three.