The End of “Insecure,” an Art Work and a Phenomenon

Across its five seasons, Issa Rae’s HBO series has given us an ever-changing and imperfect exploration of modern Black adulthood.
Issa Dee and Molly Carter from Insecure
The series is at its best when it focusses on the bond between Issa and Molly.Illustration by Tyler Mishá Barnett

When the series finale of “Insecure” airs, next month, on HBO, it will mark the end of a fascinating decade for Issa Rae, television’s heretic maven. In 2011, Rae débuted a YouTube series called “The Misadventures of Awkward Black Girl,” a rogue comedy of humiliation that attracted a cult following of young Black Internet addicts. (A stoner college freshman at the time, I was a proud member.) Rae played J, an angsty, alternative version of herself, who lived in Black Los Angeles, where she struggled to navigate work, friendship, and romance. An awkward public presence, she vented by writing aggressive raps in private. Her maladjustment was distinct from that of the contemporaneous blipster or blerd, who felt that he was specially persecuted because of his tastes; J’s awkwardness was personal, and what made “A.B.G.” click was her wry, outlandish subjectivity. She was more Larry David than Moesha.

“A.B.G.” became an example of the kind of art that Black writers could create if they sidestepped the traditional models of television-making. The Internet afforded Rae creative freedom, but it came with financial constraints: although fans funded the production of the show via Kickstarter, it was impossible for the series to turn a profit. And, besides, the box was still king. Like her contemporaries Ilana Glazer and Abbi Jacobson (“Broad City”) and Katja Blichfeld and Ben Sinclair (“High Maintenance”), Rae turned her Web series into a network deal. She would create an HBO show with Larry Wilmore, and star in it as well. Eventually, the trades shared the title of the project—“Insecure.” The artist faced an interesting dilemma: How do you preserve and transfer to an established medium the gonzo vibe of art made for online consumption? Or, better yet: Should you?

Rae, smartly, adapted to her new home. When “Insecure” premièred, five years ago, “A.B.G.” fans searched for the connective tissue. An actor or two from the Web series popped up, in minor roles. The rapping became interior monologue. The milieu was still Black L.A., but the aesthetic, pioneered by Melina Matsoukas, then a music-video director for Beyoncé and other artists, had been glammed up. “A.B.G.” was lo-fi; “Insecure” was Instagram pretty. The characters were still twentysomething and struggling to have it all, but they were decked out in designer clothes while doing so.

J was gone, and in her stead was Issa Dee, a millennial similarly frustrated by her professional and romantic ruts, which were clearly of her own creation. The explicit allusion to Rae’s name suggested a stronger link between alter ego and artist. Issa’s social world was more realized, sprawled out, bougier. (And hotter: “Insecure” will be partly remembered as a shrine to graphic hetero sex.) Some of “A.B.G.” ’s acid humor came from J’s disdain of her snide, “light-skinned bitch” colleague, Nina. “Insecure” has explored the vicissitudes of friendship—in particular, the prickly and passionate bond between Issa and her best friend, Molly (Yvonne Orji), an edgy corporate lawyer who can’t submit to love. Across its five seasons, “Insecure,” an ever-changing and imperfect exploration of modern Black adulthood, has always been at its most acute when it focusses on their relationship.

I love “Insecure.” But I have also found it exasperating. Maybe it’s my stubborn “A.B.G.” allegiance. I wanted “Insecure” to lock into a tone as quickly as its progenitor did. The early episodes felt tyrannized by their tight, half-hour structure. Although the music supervision was inspired, I tended to find the needle drops excessive. Sometimes the characters spoke not like people but like sentient trending topics. Conversely, the hammy what-do-Black-people-do conversations are part of the show’s charm. An enduring problem has been the depiction of Issa’s failing romance with her long-term boyfriend, Lawrence (Jay Ellis), a depressed, out-of-work software developer. Issa supports them both with a job she hates at We Got Y’All, a white-savior nonprofit. Their apartment doesn’t get good light, submerging the couple in darkness. Early on, Issa cheats on Lawrence with an ex, Daniel (Y’lan Noel), in what should be a shattering affair, an original sin that sets in motion Issa’s spiral of transformations. But because there’s no chemistry between Issa and Lawrence—even the chemistry of detachment, the glimmer of love lost—it’s hard to stay invested in their on-again, off-again dynamic.

What did devastate and exhilarate, all these years, was Issa and Molly. The two were part of a bigger girl group, including Tiffany (Amanda Seales), a bougie sorority sister with a seemingly picture-perfect marriage, and Kelli (Natasha Rothwell), a party-animal accountant. (As the show progressed, it gave more depth to Kelli, but Rothwell, the best performer by far, who also wrote for the series, was still drastically underused.) The intimacy between the two best friends ran bone-deep. In the pilot, Issa dragged Molly to an open-mic night, where she performed “Broken Pussy,” a rap inspired by Molly’s romantic frustration. It was funny, but it was also a violation, one that came from profound connection. The show is so good at tracking the highs and lows of this kind of platonic knowledge. The two are able to hurt each other as no man can. Much of Season 4, the strongest in the series, quietly traced the painful devolution of their trust. The final episode of Season 5 has yet to air, but I’d argue that “Insecure” has already played, in the second episode of this season, a scene of consummation: Issa and Molly, in bed, gazing at each other in platonic ecstasy.

There is “Insecure” the art work, and “Insecure” the phenomenon. The show benefitted from the chatter in the late twenty-tens about television undergoing a “Black Renaissance.” It was true, for a time, that Rae was the only Black woman with a premium-cable series. But that statistical fact obscured what made “Insecure” compelling: its sense of history and community and genre. The series has always been a sitcom about sitcoms, television about television. It was not radical; it liked tradition. There’s no “Insecure” without “Girlfriends.” Rae employed a retinue of primarily Black writers and directors who gave the show a house style. And every season, except for this last one, contained a satirical show within a show. References were made to “Living Single,” “Martin,” “Scandal.” These gags clarified the ambition of this suave experiment: to gussy up the familiar with the aesthetics of the new.

At the end of the fourth season, there was a “twist” that many viewers found intolerable. It was soapy, critics argued, to tease another reunion of Issa and Lawrence, and then to introduce an unplanned pregnancy. Fair, but “Insecure” never promised realism. It was a risk, and an admirable one, to refurbish the tropes of romantic comedy. Still, “Insecure” could surprise. Some of the best episodes were references to Richard Linklater’s “Before” trilogy: long, meandering dates, with L.A. glittering behind the lovers.

“Insecure” filled the hunger we had for a low-key Black comedy of errors. It could have remained comfort food, but as the seasons went along the storytelling matured. The characters changed; aspirations to Black excellence were refreshingly disavowed. The shenanigans alternately vexed or tantalized you. Were you Team Nathan (Kendrick Sampson) or Team Lawrence? Was Molly ridiculous for shunning a lover because he had once hooked up with a man? (She was.) You became dedicated to “Insecure” as you might become attached to a sport.

The theme of this final season is growth. The episodes I’ve seen are funny, melancholic, and not too ambitious plot-wise. The gentle momentum suggests that the series will give us an old-school, satisfying closure. The season opens with a reunion at Stanford, where the girls confront the spectres of their past selves. Molly chucks the weaves and crops her hair. Kelli is Cali Sober. Issa realizes that she has a knack for entrepreneurship. She’s empowered by her quirks, but she’s still prone to those reveries of ascension. Still Issa, in other words, but thinking about levelling up. ♦


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