Reviewing Issa Rae’s Refreshingly Nuanced HBO Comedy ‘Insecure’

If HBO’s two new comedies High Maintenance and Insecure prove one thing, it’s that web series are now officially a viable springboard to mainstream TV success. In both cases, the creators came to HBO already with fans, a library of independently produced episodes, and a fully developed creative vision, and in Insecure creator Issa Rae’s case, the 31-year-old writer/producer/director arrived at the network with the success of her Awkward Black Girl web series, her own production company, a bestselling memoir, and the backing of former Nightly Show host Larry Wilmore, who helped her develop the HBO series. Insecure is a show, then, that HBO could sign knowing it would hit the ground running, already aware of what it is and what it wants to say rather than taking a season or two to find its own voice – a voice that Rae’s character sums up in the series premiere: “Being aggressively passive is what I do best.”

That’s not to say Insecure is purely a passive show – in fact, that’s just the deceiving outer layer of what Rae is really accomplishing here. Most notably, Insecure is refreshingly stripped of all the artsy, depressing, self-absorbed weight that’s defined so many comedian-driven TV shows since Louie and replaced with an element usually absent in comedies that dip into drama: a relentlessly awkward, myopic, but undeniably likable Michael Scott-style hero. Rae’s character in Insecure has much more self-awareness, intelligence, and rap skills than Mr. Scott, but when it comes to hilariously stilted moments – the lingering pauses and interactions – Rae’s character certainly gives him a run for his money.

Rae stars in the series as Issa Dee, a 29-year-old Angeleno struggling with a stagnant relationship with her boyfriend (Jay Ellis) and her job as the only black employee at We Got Y’all, a non-profit program that “helps kids from the hood.” Yvonne Orji costars as Dee’s best friend Molly, a successful lawyer frustrated by her inability to lock down a serious relationship despite (or more likely because of) her advanced-level dating app use and tendency to cling after the first date. Together – and with some help from Issa’s occasional voiceovers and solo mirror self-reflexive pep talk/rap sessions – Issa and Molly navigate life at the end of their 20s, and the result is a wonderfully complex look at the subtle ways race, work, relationships, and female friendship intertwine in the lives of two young women. In a lot of ways, Insecure is like Broad City’s slightly older, wiser sister living on the West Coast that we never knew existed until now.

On top of all the awkward nerd-girl charm, though, Insecure also celebrates nuance in ways a lot of shows tackling wide-ranging topics like race, class, education, love, and gender often can’t quite grasp. Whether Issa and Molly are dealing with their white coworkers or the unsatisfying men in their lives, Insecure sidesteps generalizations and clichés about bad boyfriends, singledom, tokenism, and racism – both covert and overt – and focuses instead, with razor-sharp specificity, on these two characters’ daily romantic obsessions, workplace struggles, and neuroses, which are just as flawed and complicated as their friends, colleagues, and love interests. “Black women right now are always portrayed like flawless or fierce or superhuman in a sense. I feel like that’s not real right now,” Rae told Indiewire in an interview earlier this week. “I wanted to see a story about a girl who doesn’t have it all together, who isn’t that, who’s on her journey to that and what that means, what that looks like.”

Thanks to Rae – the first black woman to create and star in an HBO show – mainstream TV viewers now have a place to see what that journey looks like too, and considering she’s signed a two-year development deal with the network, we can probably look forward to much more from Rae in the coming years. On its surface, Insecure is a fresh, quietly clever comedy about conflicted 20-somethings living in a big city, but it’s also a prime example of what happens when you take a hardworking, well-established web series creator with a unique, underrepresented voice in TV and give it a bigger budget, audience, and space to play. If you haven’t checked out the Insecure series premiere yet, you can watch it in full on YouTube:

Insecure airs on HBO Sunday nights at 10:30pm.

Reviewing Issa Rae’s Refreshingly Nuanced HBO Comedy […]