When the “Insecure” series finale airs on HBO next month, it will mark the end of a fascinating decade for Issa Rae, the heretical maven of television. In 2011, Rae started a YouTube series called “The Misadventures of a Clumsy Black Girl,” a rogue humiliation comedy that drew a cult following of young black internet addicts. (A stoner freshman at the time, I was a proud member.) Rae played J, an alternate, angsty version of herself, who lived in Black Los Angeles, where she struggled to navigate. between work, friendship and romance. An awkward public presence, she broke free by writing aggressive raps in private. Its maladjustment was distinct from that of the contemporary blipster or blerd, which felt particularly persecuted because of its tastes; J’s awkwardness was personal, and what made “ABG” click was his wacky, ironic subjectivity. She was more Larry David than Moesha.
“ABG” became an example of the kind of art black writers could create if they bypassed traditional models of television creation. The internet offered Rae creative freedom, but it came with financial constraints: Although fans funded the show’s production through Kickstarter, it was impossible for the series to make a profit. And, moreover, the box was still queen. Like his contemporaries Ilana Glazer and Abbi Jacobson (“Broad City”) and Katja Blichfeld and Ben Sinclair (“High Maintenance”), Rae turned his web series into a network deal. She would create and star in an HBO show with Larry Wilmore. Finally, the trades shared the title of the project – “Insecure. The artist was faced with an interesting dilemma: how to preserve and transfer to an established medium the gonzo feel of art designed for online consumption? Or, better yet: should you?
Rae cleverly adjusted to his new home. When “Insecure” premiered five years ago, “ABG” fans searched for connective tissue. One or two cast from the web series appeared, in minor roles. Rap has become an inner monologue. The medium was still Black LA, but the aesthetic, perfected by Melina Matsoukas, then director of music videos for Beyoncé and other artists, had been embellished. “ABG” was lo-fi; “Insecure” was pretty Instagram. The characters were still twenty years old and struggling to have it all, but they were dressed in designer clothes while doing it.
J was gone, and in her place was Issa Dee, a millennial also frustrated by her professional and romantic ruts, which were clearly her own creation. The explicit allusion to Rae’s name suggested a stronger connection between the alter ego and the artist. Issa’s social world was more realized, extended, bougier. (And hotter: “Insecure” will be remembered in part as a sanctuary to straight sex.) Part of “ABG’s sour humor” comes from J’s disdain for his slutty colleague, “fair-skinned slut. “, Nina. “Insecure” explored the vicissitudes of friendship, particularly the thorny and passionate bond between Issa and her best friend, Molly (Yvonne Orji), a pissed off corporate lawyer who cannot submit to love. Throughout its five seasons, “Insecure,” an ever-evolving and imperfect exploration of modern black adulthood, has always been at its peak when it focuses on their relationship.
I like “Insecurity”. But I also found it exasperating. Perhaps this is my stubborn allegiance to “ABG”. I wanted “Insecure” to lock into a tone as quickly as its ancestor did. The first few episodes felt tyrannized by their tight half-hour structure. Although the musical supervision was inspired, I tended to find the needle drops excessive. Sometimes the characters did not speak like people but as sensitive sensitive subjects. Conversely, the hammy conversations that blacks make are part of the charm of the series. One lingering issue has been Issa’s portrayal of failing romance with longtime boyfriend Lawrence (Jay Ellis), a depressed, jobless software developer. Issa supports them both with a job she hates at We Got Y’All, a nonprofit organization of white saviors. Their apartment is not well lit, plunging the couple into darkness. Very early on, Issa cheats on Lawrence with an ex, Daniel (Y’lan Noel), in what should be a life-changing affair, an original sin that sets off Issa’s spiral of transformation. But because there’s no chemistry between Issa and Lawrence – even the chemistry of detachment, the lost glow of love – it’s hard to stay invested in their momentum from time to time.
What devastated and exalted all these years was Issa and Molly. The two were part of a larger girl group, comprising Tiffany (Amanda Seales), a candle sorority sister with a seemingly perfect marriage, and Kelli (Natasha Rothwell), a party accountant. (As the show progressed, it gave Kelli more depth, but Rothwell, the best performer by far, who also wrote for the series, was still considerably underused.) The intimacy between the two best friends was deep. In the pilot, Issa took Molly to an open mic party, where she performed “Broken Pussy,” a rap inspired by Molly’s romantic frustration. It was funny, but it was also a violation, which came from a deep connection. The show is so good at keeping up with the ups and downs of this kind of platonic knowledge. Both are capable of hurting themselves like no man can. Much of Season 4, the strongest in the series, has quietly retraced the painful devolution of their trust. The final episode of season 5 has yet to air, but I would say that “Insecure” has already played, in the second episode of this season, a scene of consumption: Issa and Molly, in bed, looking at each other in a platonic ecstatic tune.
There is “Insecure” the artwork and “Insecure” the phenomenon. The show benefited from the late twenties gossip on television going through a “Black Renaissance”. It was true, for a while, 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, community and genre. The series has always been a sitcom on sitcoms, television on television. It wasn’t radical; he loved tradition. There is no “insecurity” without “girlfriends”. Rae employed a suite of predominantly black writers and directors who gave the series a house style. And every season, except this last one, contained a satirical spectacle within a spectacle. References were made to “Living Single”, “Martin”, “Scandal”. These gags clarify the ambition of this suave experience: to sublimate 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 say, to tease another reunion of Issa and Lawrence and then introduce an unplanned pregnancy. Fair, but “Insecure” never promised realism. It was a risk, and an admirable one, to revamp the tropes of romantic comedy. Still, “Insecure” might come as a surprise. Some of the best episodes referred to Richard Linklater’s “Before” trilogy: long, winding dates, with LA glistening behind the lovers.
“Insecure” filled our hunger for a low-key dark comedy of mistakes. It could have been comfort food, but over the seasons the storytelling matured. The characters have changed; aspirations for black excellence have been refreshingly disowned. The shenanigans alternately annoyed or tormented you. Were you Team Nathan (Kendrick Sampson) or Team Lawrence? Was Molly ridiculous for avoiding a lover because he had slept with a man before? (She was.) You dedicated yourself to “Insecure” because you could get attached to a sport.
The theme for this final season is growth. The episodes I have seen are funny, soulful, and not overly ambitious in terms of the plot. The gentle momentum suggests the series will give us a satisfying old-fashioned closure. The season opens with a reunion at Stanford, where the girls face the specters of their past. Molly lets go of the weaves and cuts her hair. Kelli is Cali Sober. Issa realizes that she has a gift for entrepreneurship. She is empowered by her whims, but she is always prone to these ascension daydreams. Still Issa, in other words, but thinking about leveling up. ??