100 Favorite Shows: #79 — Insecure
By: Dave Wheelroute
Tags: TV Shows, Television, Insecure, Lists, Issa Rae

Image from The AV Club

“Hey, mirror bitch. You’re looking real clean. You’re looking real bad. You’re looking like a queen.”

After a successful web series, Awkward Black Girl, and an acclaimed book, The Misadventures of Awkward Black Girl, Issa Rae was ready to make the leap to the big time. In 2016, after years of development on a pilot for HBO alongside Larry Wilmore, Rae’s comedy vehicle, Insecure, debuted with a highly-acclaimed first season. Centered around the loves, careers, and friendship of Issa Dee (Rae) and Molly Carter (Yvonne Orji), Insecure carved out a wholly original corner for itself on HBO, where it’s resided for the past four seasons — with a fifth on the way. At a TCA session in 2016, Rae described, “This is not a hood story. This is about regular people living life.” A slice-of-life comedy with lofty, realistic goals for its Los Angeles-tied characters, Insecure is one of television’s best ongoing comfort series.

(If you’re insecure about spoilers for Insecure, this essay may not be suitable for you.)

It’s all in the title, baby. The characters on Insecure can be incredibly insecure. It’s just more frequent in Issa and Molly than in the rest of their friend group and romantic interests. Themes of insecurity and discomfort in all situations — primarily social — are found throughout all episodes of Insecure, but the penultimate episode of season two, “Hella Disrespectful,” portrays it with tension during a birthday party that is on the level of Fleabag’s second season reunion dinner and the infamous “Dinner Party” on The Office.

The birthday in question is Derek’s (Wade Allain-Marcus) and it’s put together by Tiffany (Amanda Seales), who describes Derek as “the Barack to [her] Michelle,” prompting an immediate eye roll from Issa. For Tiffany and Derek, it’s a perfectly performative birthday dinner used to present themselves as the happiest among their friend group. For Issa and Molly, whose perspective we view the dinner through, the constant interruptions and uncomfortable ex-lover reunions (Lawrence (Jay Ellis) turns up because of course he does) make them feel distinctly unwelcome at the sit-down dinner. Both are different versions of insecurity; Issa and Molly just wear it more directly.

Of course, Derek’s birthday party comes near the end of an episode that also features Issa’s shaken ambition after her Latino outreach program for We Got Y’all is stymied by discrimination and Molly’s uncertainty over how to deal with the hurt stemming from her relationship with Dro (Sarunas J. Jackson). Whether they’re venting to each other (after agreeing not to judge one another) or venting to the ex-lovers in question or their parents, Issa and Molly show they have plenty to worry about in their own lives without feeling like they need to prove themselves at an arbitrary birthday party.

Social norms dictate their presence at Derek’s celebration, but they’re still both outspoken women who refuse to let general niceties among their friendships impede the progress they’re striving for in their personal and professional lives. The futures of their careers are always in question, whether they’re leading audacious new initiatives at work or simply taking steps to better build up their résumés. Often times, their work lives are only as effective as the relationships they build with colleagues, as evidenced by Issa paying the debt of botched presentations through her initiative and reformation with Frieda (Lisa Joyce).

Image from Popsugar

Relationship-wise, though, forgiveness is messier. Throughout Insecure, it seems like Molly is constantly on the verge of a break-up, whether it’s with the aforementioned Dro or the “perfect on paper” Andrew (Alexander Hodge). Love is not so easy and Molly is the quickest one in the friend group to choose her career over her dating arcs. Issa, on the other hand, is caught in a revolving door loop of the same men, from the friend with benefits, Daniel (Y’lan Noel), to the long-term, invisible-string-tethered boyfriend, Lawrence.

The way Issa deals with the fallout of linking back up with Lawrence at Derek’s party is stunningly moving. Arguing outside of the venue, Issa brings up how much support she provided Lawrence when he was depressed, directionless, and an overall bummer to be around. She’s not evoking her actions to say that she’s owed something by his rejuvenated personality, but rather to express her complicated emotions. At once, Issa is both overjoyed to see Lawrence putting himself together, but she’s also enormously regretful to not be the woman in his life who can reap the benefits of her own scaffolding for emotional recovery. It’s a devastating notion to miss out on the life you fought to build, in favor of someone who never weathered the hard parts of a relationship (even if this wasn’t the intended “reward” of building), and it culminates in Issa’s destruction of the furniture in her apartment to the tune of Kelela’s “Frontline.”

Just as in “Racist as Fuck,” when a timeline of Issa’s highs and lows of her youth and relationship are depicted via time lapse on a stationary couch, furniture is shown to be an important symbol on Insecure. In the time lapse, furniture is a constant. A symbol of steadiness. It’s the recognition that, for as tumultuous as a life can be when it’s set out on its own, there’s always some form of comfort to come back to. Couches don’t leave, even when people do, after all. But something is clearly broken in Issa in “Hella Disrespectful” when she demolishes her own belongings and her own “home base” in life. The outward damage is merely reflective of the turmoil percolating within Issa.

Image from Amazon

While Issa’s relationship with Lawrence is the primary romantic vehicle of the show (to the point where the idea of forcing it into a casing of long distance is bandied about during season four), all sorts of relationships are depicted on Insecure. Flings, affairs, marriages, crushes. No one character is on the same romantic plane as another during the series, but they’re also not in competition with one another. Life stages vary from character to character and Insecure presents us a prism to experience each of them, rising and falling with the arcs of each season. For all of the inherent insecurity, such discomfort is mocked with a high spirit thanks to Insecure’s specific sensibility, bringing the enormity of certain relationships down to Earth by dealing with them in sexually open, tongue-in-cheek (cheeks pending) manners.

This is Insecure. It’s extremely specific and Issa Rae’s real-world experiences are invested within Issa Dee and her friend group. This kind of lived-in authenticity makes the show one of the easiest on television to just flick on and relax to (reruns of Insecure are more nurturing than most HBO comedies), especially because of the series’ stunning visuals and well-lit depictions of Inglewood, Malibu, and other Californian locales. (The director arsenal on Insecure is doubly impressive, counting Melina Matsoukas, Prentice Penny, Regina King, and Kerry Washington among their visual filmmakers.) But it also helps us become emotionally invested in this core group of characters. The women on Insecure are the ones the show’s creative staff is committed to at every turn as the team is hellbent on bringing the characters closer to fulfillment on their quests for joy. Issa, Molly, Tiffany, and Kelli (Natasha Rothwell) are experiencing their lives together, after all. You don’t always get multiple chances at finding a friend group worthy of sharing your ups and downs with, but this foursome is (for the most part) loyal, if occasionally grating. That’s what your younger years are for, after all. Ups and downs, highs and lows, and the ones who are there through them all.

The easy-going nature of Insecure is vital, considering how shit can get real pretty quick and we need the sense of comfort to feel like their worlds aren’t being blown up. At least, that’s the sense I got from the beginning of season three’s “High-Like” (my favorite installment), which begins with Issa driving for Lyft (a perfect job for the transient moment in her life). When she pulls into a new pick-up spot, her passenger asks for transportation to the Brenshaw Mall, but oh, shit! It’s not just a random Lyft user; it’s Thug Yoda (Tristen J. Winger), the wise and kind neighbor involved in some unkind and unwise activities!

Image from Vulture

In “High-Like,” there’s a ton of fun moments, but there’s also raw emotions dealt with, so the presence of Thug Yoda helped put me at ease in order for the rest of the episode to just wash over me. It’s what I imagine edibles feel like (read: Scooby Snacks. Oh my gosh, the Scooby-Doo fruit snacks are just begging for a liberally-minded cross-promotion), especially after watching Kelli eat one ahead of the foursome’s trip to Coachella and then succumb to demolishing fits of laughter.

Drugs (weed and molly, primarily) are a big part of the ladies’ experience at Coachella, but they’re about the only thing all four had in common during the music festival in the desert. Molly (who initially doesn’t attend until Issa convinces her, due to how the experience would be more fun with her best friend) is obsessed with her work. Kelli picks a fight when concert goers challenge whether or not she belongs at Coachella. Issa is determined to hook up with Nathan (Kendrick Sampson). And Tiffany is ultimately just sad that the Coachella weekend is billed as a “last hurrah” for their friend group.

It’s not easy for the four of them to live in the moment. When Issa takes molly, her first question to Nathan is, “What’s wrong with me?” before continuing, “I feel good.” She gives into her impulses by rhyming “pressed” with “Crest” and conjuring up the idea of “Inglechella” after Nathan remarks that he doesn’t want to come on too strongly with his attraction towards Issa. She also ignores her inhibitions and becomes intimate with Nathan in a futuristic-looking Ferris wheel. Ultimately, though, Issa is unable to trust her own feelings of euphoria and she becomes consumed with the worry that her friends are mad at her for linking with Nathan over them, especially when they wound up banished from the festival before Beyoncé took the stage.

Molly, on the other hand, takes molly (“Molly squared,” she dubs it) and winds up trying to convince herself she’s living in the moment by smiling and dancing, but is ultimately unable to let even party drugs take her attention away from her work notifications. (Though, it does lead to a hilarious sequence featuring Molly, with dilated pupils, typing gibberish into her laptop.)

Image from The New York Times

Heading into the weekend, all four were keen to party with complete abandon and savor the impermanence of four friends hanging out at Coachella. Before their irrepressible worries and hold-ups set in, they convinced themselves that there was plenty of time for responsibility. What could a few days of partying and having fun and vibing out to great music hurt? Of course, they can’t let go of their personal drama and professional goals, which follow them out to a desert with poor Internet reception. There’s plenty of time for these obligations, but they’re not truly letting go and living in the moment and, as a result, the obligations are seen as the most important thing to accomplish late in the evening while on a confluence of drugs.

Following the poor reaction to Coachella, the episode concludes with Tiffany confiding in Issa that she feels left out of the friend group and she’s worried about how much their lives are going to change. For years, there was comfort in a friend group becoming one’s surrogate family and there were myriad moments and memories of merry mirth to look forward to when the going got tough at work or when a relationship flickered out. But Tiffany recognizes how much their lives are changing and how much shit is different for all of them. It’s a heartbreaking realization that’s all too relatable for any viewer who has become aware of the last days of the glory era of their youthful friend groups. It’s just as challenging when you’re the one perceived to have your life together in forward motion as it is when you’re the one perceived to need the group the most.

I’ve wondered a lot about whether a group of friends can be a true group of friends when one person feels insecure about the legitimacy and longevity of the friendships. “If they’re your true friends, you never need to feel insecure about them,” I’ve been told plenty of times over the years. But sometimes you just can’t help it. No matter how much love is shared, doubt can always creep in, especially when insecurity is a base personality trait of yours or of mine or of Issa’s. At the end of the day, shit is going to change, whether or not a weekend at Coachella is the cherry on top of a lifetime of “friendship goals” and solid Stanford-founded camaraderie. It’s easy to be insecure about that; believe me, I know. But the ultimate lesson of “High-Like” is to just let go. Even for a little bit. There’s no substitute for experience.