Watching "Insecure" And Grieving For A World That No Longer Exists

Filmed before the coronavirus locked down most of the world, the new seasons of Insecure and High Maintenance are stark reminders of a world that doesn't exist anymore. (Spoilers for High Maintenance.)

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It took less than 10 minutes once I started watching the new season of Insecure for a throwaway line to jolt me back to our new, sobering reality. Issa (Issa Rae) and Molly (Yvonne Orji) are shopping at a clothing store talking about Molly’s hot (!!!) new potential bae, Andrew (Alexander Hodge). “A nigga got jungle fever and he is infected,” jokes Molly. “Okay, he patient zero in this motherfucker!” replies Issa. It’s an innocuous-enough joke, par for the course for the characters — but watching this episode weeks into pandemic-induced lockdown, I was jarred.

Though this new fourth season of Rae’s HBO comedy was obviously written and filmed before the coronavirus outbreak shut down most of the world, watching the five episodes of Insecure made available for critics felt like strapping myself into a time machine and traveling back to an alternate universe. It’s a world where people in Los Angeles still go to busy coffee shops and bowling alleys, instigate late-night booty calls, and hike on Sundays with people they don’t live with. That the new season is centered around Issa’s attempts to mount a block party in Inglewood certainly doesn’t help with the surreality of watching the show now. Remember block parties? Where strangers inevitably rub up against each other, jostling to see the headliner, eating street food with their germ-infested, unwashed hands?

Insecure is not the only TV show where this disconnect will occur, of course; new and forthcoming seasons of many series that are supposed to be set in contemporary times will automatically seem antiquated by default when they eventually air. The new fourth season of High Maintenance, whose finale aired on HBO last Friday, is also wild to watch now — hinging as it does on chance encounters between New Yorkers and a weed dealer who isn't afraid to visit people's apartments without personal protective equipment.

Both shows adhere to a certain kind of verisimilitude. They’re both comedies anchored by the details of daily life in bustling big cities that allude to current events, be they politics or economic struggles, in a way that makes watching them now, as we live through an unprecedented time, feel particularly strange. They are stark reminders of the world we used to live in — a world that doesn’t exist anymore.

From its conception, Insecure has straddled the line between being aspirational and realistic. While there was a noted and unexplained cosmetic glow-up for every character in Season 2, some uncomfortable realities have also found their way into this sun-kissed LA, where a surplus of beautiful black men of all shades date dark-skinned black women with natural hair.

In Season 3, Trump’s election — and the ancillary bigotry against Latino people that has festered since then — appears in subtle ways. Issa and Frieda (Lisa Joyce), her coworker at the perennially out-of-touch education nonprofit We Got Y’all, run into an issue at the school they have been assigned to volunteer with. It appears that the vice principal, a black man with a grating laugh, doesn’t like Latino students and won’t help Issa and Frieda try to increase enrollment with that demographic. Issa’s doomed efforts to solve the problem eventually lead to her being demoted. It’s a subtle example of a tension that is all too real — bigotry against Latinos in the black community does exist, and figuring out how to navigate that in white spaces can be difficult. In other newsy plot points, Molly finds out she’s been making less money at work than her white peers, and Lawrence (Jay Ellis) has an app idea that isn’t properly critiqued because his white liberal bosses are too afraid of offending him to offer useful feedback.

I couldn’t stop thinking about how screwed Issa would be in the current recession. 

Economic precarity is a part of this world too. Lawrence starts the series unemployed and has to humble himself by taking a sales job at Best Buy; when Issa’s rent goes up in Season 2, she’s forced to move out of her apartment and ends up (inexplicably, given that she has family in the area) living with a former boo for the free rent. She also starts driving for Lyft.

Watching this new season, I couldn’t stop thinking about how screwed Issa would be in the current recession. Her nascent career in event planning would be shuttered. It’s unlikely she’d be able to make any real money driving with Lyft — even if she were willing to risk her health by picking up passengers. And certain aspects of Insecure that already bothered me, like the frustrating class stereotyping that rears its ugly head again in the season premiere, feel even more obnoxious given our current economic reality. Issa is a property manager, and her interactions with tenants like Trina, a single mom with an attitude, are supposed to be comic relief. But in light of the disproportionate number of black people who will be devastated by the developing recession and are unable to build wealth through homeownership, the jokes feel in poor taste.

This is not to say that the new season of Insecure is bad. The petty relationship dramas that fuel the show are still compelling; the sex scenes are both funny and hot, and there are some great one-liners. (“That missionary be hitting though.”) The outfits and hairstyles alone will make you ache to go to a day party — and then wonder when you’ll ever be able to go to a party again. Such is everyday life with the coronavirus; it infects our ability to enjoy even simple pleasures.

High Maintenance offers a similarly jarring viewer experience, depicting a New York City teeming with moments of poignant, unexpected community. A charming weed dealer known only as The Guy (Ben Sinclair) traipses around the city on his bike selling pot as viewers get peeks into the lives of his buyers — from This American Life producers to an Upper East Side doorman.

The latest season, its fourth on HBO, has been uneven, though there have been certain standout episodes: “Trick,” a moving look at the life of an intimacy coordinator and her asexual love interest, and “Solo,” about a trans man’s crushing inability to be alone (you certainly wonder how he’d cope in self-isolation). High Maintenance, beloved by “coastal elites” like myself, certainly has a tendency to give its nonwhite and lower-income characters “some quirk, hidden talent or non­-normative sexuality,” thus “depend[ing] on its audience’s prejudices in order to undercut them,” as writer Willy Staley put it in an essay for the New York Times Magazine. But the series’ ability to remind us how similar we ultimately are to one another can still be very moving, even if it is a little cloying.

It's difficult not to feel some kind of nebulous grief.

That sensibility has been baked into the DNA of the show, ever since Ben Sinclair and Katja Blichfeld created it as a web series back in 2012, before HBO picked it up in 2016. Take the Season 2 premiere, “Globo.” In the episode, an unexplained national event (probably the 2016 election, but it’s not explicit) leaves the city reeling. People check their phones in dismay. Therapists are calling in sick, unable to help their clients.

“Thank god you’re working, ‘cause I woke up to an email that was like, ‘Hey, Brian, we really need you to come in today,’ and I was like, did you read the fucking news?” says one of The Guy’s customers, played with pitch-perfect hysteria by Bowen Yang. The episode ends with a train car of subway passengers trying to keep a little boy’s balloon in the air as he and his dad ride home after a long day. The implicit message: In moments of great stress and uncertainty, we seek solace where we can find it, even in the company of strangers.

That same idea is also present in the most recent season finale. A Nor’easter upends travel plans for a flight attendant and her sister, so they are forced to stay at her airline’s crash pad — a small apartment full of flight attendants from all over the world, waiting to get to their next destination on Christmas Day. It’s a peak High Maintenance setup: all these people unexpectedly in one place, making due in a power outage and with limited bed space.

Watching the episode, which also features The Guy and his niece having a meaningful heart-to-heart over Hanukkah donuts, the reality of some of the more intangible things this current pandemic has taken from all of us really hits home. In past moments of great tragedy or uncertainty or disaster, yes, we’ve hunkered down with loved ones — but we also go to the neighborhood bar or restaurant, talk to strangers on the street, offer platitudes to each other in attempts to make sense of it all. Such things are rightfully impossible to do now. It's difficult not to feel some kind of nebulous grief as a result.

In the last scene of the finale, we see The Guy in the airport, embarking on a spontaneous solo trip to New Zealand. As he walks to his gate, the camera lingers on passersby heading toward their own destinations. It’s a fitting note for the show to end on, especially if the series isn’t renewed for another season. Airports are hubs, full of strangers going about their business, all with thousands of stories individual to them, vectors of commerce and companionship. But now the specter of our current crisis looms over all of this, and we inevitably see all those people as vectors of something much more sinister. ●

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