What Insecure Gave Us

Over the course of its five-season run, Insecure was many things, at times intangible and frustratingly hard to pin down from one episode to the next. Perhaps that’s what kept me motivated to watch it even after I lost a vested interest in its characters and storylines; I was always invested in the story of the show itself as a cultural artifact, in what it meant for a series centered on Black women to become such an indelible part of the zeitgeist.

When it debuted on HBO in 2016, Insecure appeared to follow in the tradition of groundbreaking comedies like Living Single and Girlfriends, which chronicled the careers and romances of Black women in their twenties and thirties. But you can’t talk about Insecure without talking about The Misadventures of Awkward Black Girl, the web series that helped launch Issa Rae’s television career when it premiered on YouTube in 2011. Awkward Black Girl was the foundation on which Insecure was built, the blueprint for the show’s ultimate success.

Awkward Black Girl told the story of J, a late-twenty-something-year-old living in Los Angeles, navigating the frustrations of an unremarkable love life and an unfulfilling nonprofit job. J, much like Insecure’s Issa Dee, was passionate and well-meaning but perennially at a loss for how to attain the life she truly wanted.

The web series, with its offbeat Seinfeldian humor and charming DIY aesthetics, became a cult favorite on the internet among young Black millennials. Through conversations in the comments and across social media, fans championed ABG enough for Rae to eventually attract an invitation to develop a pilot in 2013.

When Insecure finally premiered in 2016, part of my desire to watch it was this history. Rae had managed to create her own lane within mainstream entertainment by giving the industry no choice but to acknowledge the influence of the work she had manifested outside of traditional structures. For a lot of young Black women, watching Awkward Black Girl was a monumental first—a first time feeling seen, and/or a first time seeing a Black female protagonist who acted like J, painfully awkward and unsure. The success of the series unveiled an eager audience that mainstream entertainment had largely ignored. Insecure was, potentially, the show that would remedy this neglect.

As a fan of Awkward Black Girl, I was proud of Rae for making it to a bigger platform. I was also curious. With a real budget, a writers’ room, and the goodwill of every fan who had followed her since 2011, how could a scrappy web series transition into a marquee HBO primetime show?

In an interview with Time, Rae revealed that one of her main goals in the transition from the web to TV was for Insecure to fling doors wide open to Black storytellers, particularly inexperienced ones like herself who had yet to be given a chance to prove themselves in the writers’ room or behind the camera.¹ “That was a super-conscious effort: It was like ‘Oh, the door is open to everybody—come on in,’” she said. “If we only get one season, at least you can say you have this experience and get on to the next show.”

Of course, Insecure got more than a season and eventually accomplished Rae’s mission of creating a structural ripple effect for Black creatives in the television industry. Not long after the Insecure series finale aired, writers’ room alum Mike Gauyo posted a Twitter thread chronicling the countless writers and producers from the show, beyond Rae and showrunner Prentice Penny, with projects coming in 2022. The thread was fourteen tweets long, shouting out Grace Edwards’s forthcoming Daria spinoff, Jodie; NBC’s Grand Crew from Phila Augusta Jackson; Dayne Lynne North’s highly anticipated Best Man series; Gauyo’s own forthcoming AMC series Send Help; and more.

More ripple effects can be seen in the wave of new series in the years since Insecure premiered centered on the fun, messy lives of Black millennial creatives, including Twenties, Run the World, and Harlem (created by Awkward Black Girl actor and cowriter Tracy Oliver). It could be argued that these shows—centered on themes of Black female friendship, joy, love, and drama—had a smoother transition into the television landscape because Insecure served as a successful, contemporary precedent.

And then there was the discourse.

There is a picture of Rae, posted to her Twitter the night of Insecure’s second season premiere in July 2017, in which she stands in front of a huge screen filled with dozens of tweets from fans reacting to the episode. This image is a visual representation of the relationship between Insecure and its audience, a constant dialogue. “I follow the hashtags,” Rae confirmed on a 2017 episode of the now-defunct Desus & Mero show on Viceland. “We always gather at somebody’s house, a writer’s house, to watch the episodes live and follow the tweets, and then we discuss it.”

There was much to discuss because Twitter lit up with thousands of hot takes on Sunday nights. Early on, the main Insecure discourse revolved around the messy dissolution of Issa Dee’s stagnant five-year relationship with Lawrence (Jay Ellis), followed by her disbelief and indignance at his professional and personal glow-up after their breakup. Each became the villain or the hero of the series, depending on who was weighing in. Memes were made, threads were written. The #LawrenceHive and #TeamIssa hashtags trended as the demise of the fictional couple’s relationship granted an excuse for Black Twitter to unpack the deep hurt and tension between Black men and women on the app and in life.

Insecure became very adept at creating storylines calibrated to generate conversations that became bigger than the storylines themselves. Trending topics the series inspired included: the racial and social dynamics of giving blow jobs when Issa called Tiffany (Amanda Seales) Becky for deigning to go down on her man; the validity of open marriages after Molly’s (Yvonne Orji) entanglement with Dro; postpartum depression; Black people who know how to play Spades versus those who don’t; the best regional barbecue; and whether fictional characters should be allowed to wear Black Greek paraphernalia.

This dialogue provided tangible proof to HBO, to everyone, that Insecure was successful and impactful enough to generate cultural discussions that would keep people watching week after week. This knack for generating trending topics was clearly part of the plan. Rae, with her background as a web series creator, understood what many shows have since replicated (Euphoria easily comes to mind). While social media may not constitute a show’s entire audience, the ability to mobilize people online to care about and talk about your series is the key to the survival of any series these days. Strong ratings and a strong online presence equal success. 

I never directly engaged with the online conversations myself, but they were so ubiquitous on platforms like Twitter and Instagram that it was impossible to be unaware of them. The conversations I was having with friends about the show offline were mostly about how solidly Insecure had managed to embed itself in the culture, creating an almost communal watching experience that included not just loyal viewers but anyone with a Twitter handle and an opinion. Was the show’s entanglement with the Timeline to its detriment or to its advantage? And what about strong storytelling?

As critic Angelica Jade Bastien aptly put it in a review, “Insecure is the kind of series meant to be experienced but not studied;” with storylines like the Condola baby bomb, it was often “all soap operatics, no depth.” The draw of Insecure was its ability to make the everyday and mundane feel like an escape, like kiki-ing over drinks with friends. There were lots of vibes: excellent music supervision by Raphael Saadiq; slick and stylish direction by Melina Mastoukas; beautifully lit, melanated skin and LA vistas shot by cinematographer Ava Berkofsky. 

When I think about Insecure—not just the discourse around it—I think mostly about the vibes, the fact that the way the show looked was as important to its DNA as its understanding of how to harness and engage with a social media audience. It was not a coherent plot or fully developed characters that defined the show, but the way it visually centered the Black femme body and the landscape of Black LA, a beautiful collage of cinematography, music, and costume design that elevated every episode into, ultimately, a celebration of Black beauty. 

Vibes do indeed make for beautiful TV. They don’t always make for compelling stories. By season 3 of Insecure, after the Lawrence versus Issa drama was seemingly over, the storylines devolved, running aimless circles within the confines of a tricky half-hour comedy runtime. They were still juicy enough to encourage Twitter debate, of course, but they didn’t always make sense for the characters themselves. It’s not a bad thing that Insecure pulled from the culture it sought to represent. It’s just that it didn’t always feel as though it had much to really say about any of these topics. Instead, it presented scenarios that functioned more as discussion prompts than mechanisms for the story to move forward organically. It was the audience who had something to say, who would in a sense reflect back to Insecure what its themes represented. 

Awkward Black Girl was different: surer of its narrative tone and point of view, more engaged with the audience’s conversations but perhaps less beholden to the crowd. On Insecure, we see this with the breakdown of Molly and Issa’s relationship in season 4. This provided a lot of fodder for debate, leading to an eventual Molly backlash online that perplexed the writers, who thought it came across that both Molly and Issa had been bad friends (it hadn’t). This storyline catalyzed a lot of interesting Twitter threads and think pieces about the reality of friendship breakups, but to me it was an example of the show presenting a juicy plotline with a bang, only to eventually resolve it with a whimper. 

In the series finale, a convenient time jump allowed for an entire season’s worth of friendship drama to be wrapped up with a frantically tied bow. The loving moment shared between Issa and Molly after the latter’s wedding was beautiful, yes, but also very tacked on. With as much time that was spent chronicling the disintegration of their friendship and as much debate that this breakdown had generated, the lack of time dedicated to their tenuous reconciliation felt like a letdown. Particularly because Issa and Molly, not Issa and Lawrence, were the core relationship of the show. 

When I think a lot about the layered meta-narrative of the show, particularly Issa Dee’s on-screen glow-up in the context of Issa Rae’s real-life glow-up, it’s clear Insecure always shined when it revealed the awkwardness of life and the constant yearning so many of us feel as we enter true adulthood—a yearning for the completion we think will come with the right job or the right partner. It’s impossible to know how much the pressure was internal or external, but it’s palpable to me when I watch the show. The sleeker Insecure got, the more distant it felt from its Awkward Black Girl roots and the vaguer it became in its point of view. Similarly, the more successful Rae became—the more polished, the more relevant—the more pressure, I imagine, there was to make herself and Insecure a gate opener, a legacy builder.

In a 2021 interview with Taryn Finley, Rae spoke candidly about what she believes comes next: “I’m back to feeling like, ‘OK, will I have longevity past this?’ . . . I’m entering into the next chapter and my next phase. I had a web series. I have a TV show. Kind of, what else can I do? And how else can I have an impact? And I don’t know.” Rae’s statement mirrors the entire last season of Insecure. The “I don’t know,” this anxiety around whether we’re ever—no matter how much we grow—doing enough, doing good. 

Insecure’s preoccupation with making the right choices—with legacy as it tried to model achievement, with making boss moves—hinted at the reality of modern life: no amount of achievement can bring inner peace. Watching the final season, I think a lot about these moments of incompleteness among the happy endings: when the gang visits Tiffany in Denver, she admits she hates it and is depressed; Molly jokingly (or not?) complains about how Taurean won’t leave her alone during their honeymoon. 

And then there’s Issa Dee’s ending. 

What I loved most on Insecure was the ongoing motif of Issa’s mirror monologues. Struggling with some personal crisis—cheating on Lawrence, navigating microaggressions at We Got Y’all, dealing with tensions with Molly—Issa would look at her reflection in a bathroom mirror and try on different versions of herself. Her reflection, in a sense, became another character, serving as a sounding board, an agitator, a glimpse into her inner life. These moments offered rare honest reflections of who Issa really was outside of the gloss and the drama, imbued with humor, nuance, and the kind of candid vulnerability that seeps out when no one’s watching. 

In that final scene, Issa Dee looks into the bathroom mirror, smiles at herself, and walks out of frame. There’s an uneasiness, intended or not. She stares confidently at her reflection in the mirror. She’s finally accepting the unknown of her future, but that uneasiness is still there. Even so, for the first time, her reflection has no self-deprecating quip to offer. She walks out of the bathroom and out of frame as Kelis’s “Bossy” begins to play. The uncertainty, however optimistic, still lingers in the frame. Some found this an abrupt way to end, but we can’t know ultimately what will really happen with Lawrence, with the Blocc, with anything in Issa’s world. Perhaps that’s not the point. Happy endings, after all, are not absolute. We leave Issa and the series mid-life, mid-journey. This uneasiness with what comes after getting what you want seems apt though. Insecure always felt inextricably linked to Rae’s legacy; she and the character shared the same name and experienced parallel professional glow-ups. So, it makes sense that legacy was the overarching theme and preoccupation of the show’s final season, if not its entire run.

Issa Dee seems to understand that the messiness and uncertainty of life don’t create insecurity. Now there is acceptance. Acceptance, after all, is what it truly means to feel seen-–not only by the culture, but by yourself. 

I know that ultimately whether a show is “good” or “bad” is often the least interesting way to engage with it, but in this context I’m grappling with the nature of my own subjectivity as a viewer and as a critic. How do expectations of greatness shape the way we, as Black people, make art and experience it? Particularly in the context of white supremacist systems that have excluded and obscured depictions of Black life? We’re “rooting for everybody Black,” hoping that through “success,” through “goodness,” we can allow more Black stories by Black storytellers to push through the gates. It’s a horribly unfair paradigm, one that I suspect made Insecure prioritize generating trending topics at the cost of actual narrative depth.

But this question of legacy seems to be at odds with a show about imperfection, specifically the imperfection of Black women. Is thinking about legacy in the larger sense too limiting? Does it compromise the imperfect nature of creating art? I wonder if the tweets, the profiles, the legacy of it all can be equal parts uplifting and overwhelming. Television in the current age is in some ways bound to the online discourse it generates. People watch shows because they trend, and from there we must reverse-engineer an explanation for why the show is trending. There are shows that excel in pushing forward narrative and others that excel in channeling the mundane into something cozy, uncomplicated, and fun. In seeking this complicated fun by a show like Insecure, the audience can often view a show with an uncritical eye, boiling it down to a brand, or an aesthetic, or a trending topic. Insecure was a gift, an affirming exhibition of Black millennial life. But in the whirlwind of the show’s success, its point of view became an afterthought, and thus who Issa Dee is or was got lost for me. Now that it’s over, this mixture of affection and ambivalence I have for the series is clear: Insecure gave us a lot, and yet it left me wanting more.