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‘Insecure’ Took the Long Way Here — and It Paid Off

How Issa Rae’s comedy benefited from an arduous evolution


For a show that’s been in the works for more than three years, Insecure feels effortless.

In August 2015, The New York Times Magazine ran a profile of its creator and star titled “The Misadventures of Issa Rae.” Partly, the headline was a play on The Misadventures of Awkward Black Girl, the DIY web series that landed Rae on the map when she debuted it in 2011, just four years out of college. Partly, though, the piece was about Rae’s very real career frustrations. Its central question was as simple as it was thorny: Why couldn’t Rae translate her buzz and talent — particularly as a young black woman at a time when the industry was theoretically more open to diversity and representation than it had been in decades — into an actual show?

At the time, Rae had been through every kind of wringer Hollywood has to offer new talent. There were the offers to adapt Misadventures but also water it down to an almost comical extent. There was an abortive collaboration with Shonda Rhimes on an ABC pilot called I Hate L.A. Dudes. And finally, there was Insecure, which was still without a costar, showrunner, or filmed pilot and two months from a series order. An HBO half hour seemed like the light at the end of the tunnel, but that light was still depressingly far off.

One cocreator (Larry Wilmore, who had collaborated with Rae previously and was brought on for his experience), one showrunner (Prentice Penny, ditto), and more than a year later, Insecure has arrived at long last, fully formed from the start. The show’s long gestation hasn’t muffled Rae’s voice, which is Insecure’s clear and distinct center. It’s buttressed and amplified it, yielding a series that’s as comfortable expanding outward from its protagonist as it is turning inward on her hangups, fears, and of course, insecurities.

Insecure has many strains of the self-reflexive, comedian-as-auteur show in its DNA, and it’s certainly been marketed as such. The advertising alone — an anxious, skeptical photo of Rae with the tagline “She’s trying hard AF” — promises another pre-fame self-portrait, starring a version of the creator with a similar sense of humor and chosen career but less success or even drive to succeed. (Think Hannah Horvath, or Dev Shah, or Abbi-and-Ilana.) Rae’s character certainly fits the bill: She’s 29 to Rae’s 31 and lives in Rae’s hometown of Los Angeles, home of the aimless and creatively unfulfilled. She’s even named Issa.

But Insecure isn’t interested in being a painfully autobiographical dramedy — and thank goodness for that, since that type of show has only multiplied in the time Insecure took to iron out its kinks. For one thing, Rae’s character isn’t interested in show business and she doesn’t live in Hollywood. She’s an education nonprofit worker living south of the 10 freeway, the unofficial dividing line that separates white Los Angeles (Silver Lake, Brentwood) from black (Leimert Park, Inglewood). She likes to rap, but in private — it’s an outlet for the aggression and brutal honesty she normally keeps bottled up, not a potential career. “Issa” can’t bring herself to tell her longtime boyfriend that she’s sick of his underemployed funk, or tell her condescending coworkers that she can hear them talking shit in the break room, so she takes it out on the mirror. As a narrative device that tells us what’s going on inside the head of a character partly defined by her reserve, it’s also a handy replacement for the voice-over that was a hallmark of Misadventures — and allows for a fantastic cameo I won’t spoil here.

Insecure takes advantage of its setting, which has more in common with the ’90s black sitcoms that Rae grew up on than 2010s hipster ones by offering up a whole ensemble, not just Rae. We’re saturated with L.A. shows about characters airing their sorrows in Palisades ranch houses and mansions in the hills. We’ve barely gotten a taste of what it’s like to live in a rundown apartment complex with a neighbor who refuses to use the letter c. Insecure adds texture to both its sense of place and the people who live there. That slacker boyfriend, Lawrence (Jay Ellis), isn’t just a one-note dead weight for Issa to shed before the real show begins. He’s a Georgetown grad struggling with his inability to turn his degree into success. We see both why he and Issa clicked for so long — there’s a lovely flashback that lays out the history of their relationship through the couple’s shared couch — and why they’ve sunk into a malaise.

Meanwhile, as Issa’s best friend Molly, Yvonne Orji is a proper costar. In some ways, Molly’s got it more conventionally together than her friend; as a corporate attorney with a glitzy downtown apartment, she’s certainly in better financial shape. But where other shows might make Molly into a Marnie Michaels–style foil, destined for a downfall or bandied about to make Issa feel bad about herself, Molly gets problems, and screen time, of her own. Through that ensemble, Insecure shows a wide cross-section of life as a young black person in Los Angeles by simply being about these specific young black people in Los Angeles.

Insecure isn’t about a person so much as a milieu. In that respect, it’s similar to Atlanta, another new show by a multihyphenate creator long overdue for a vehicle who opted for a mood piece instead. Rae and her collaborators have taken the burden off a singular heroine and the time to build out a complete world, one that features a deadpan sense of humor, a fully developed female friendship, and a setting we’re nowhere close to seeing enough of on our screens without being defined by any one of those things. And in taking a thoroughly contemporary sensibility and broadening it into a classic sitcom-style range, it’s a hard-earned fusion of Rae’s perspective and Wilmore’s specialty. For Rae and for us, the wait was worth it.

Disclosure: HBO is an initial investor in The Ringer.