No Reason To Pretend: ‘Insecure’ Finds Security In Rap

No Reason To Pretend is a weekly column by Stephen Kearse that explores the intersection of hip-hop and pop culture.

Issa, the main character of HBO’s Insecure, spends a fair share of her time in front of mirrors, rapping. Her raps, always self-written, are bad. The words fumble out, inflected at odd points, and connected by clumsy, simple rhymes. This roughness is intentional — Issa tends to turn toward rapping when she’s particularly emotional or facing hard decisions — and actor/writer Issa Rae, a veteran practitioner of awkwardness, sells it well. She truly cannot rap, and it’s funny to see her repeatedly try. But it’s not just a joke. The motif’s real treat is the explosive confidence that rapping always manages to create, however briefly. In a show about deeply ingrained insecurity, rap is a continual source of fleeting but thorough conviction.

Issa Rae has a well-documented history with rap. J, the protagonist of Rae’s breakout web series The Adventures Of Awkward Black Girl, also loved to rhyme. The show frequently played this up, giving her a rap song as a ringtone, jump-cutting to uncomfortable freestyles, and dedicating entire scenes to J enthusiastically reciting ratchet romps in the privacy of her car. The show’s soundtrack was just as driven by rap, featuring interludes backed by Ice Cube, Wiz Khalifa, Childish Gambino, 50 Cent and others. The Doublemint Twins, a joke group that Rae is actually a member of, also have a few choice features on the show. Outside of ABG, Rae once ran a vlog series titled Ratchetpiece Theatre, where she snarkily dissected various rap songs.

Rae’s previous forays with rap often toed an uncomfortable line between appreciation and dismissal. Ratchetpiece Theatre, for example, would often closely scrutinize songs just to mock them. “Nothing depresses a stunting rapper more than if nobody’s around and nobody’s stunting,” she sneered in her study of Rocko’s “U.O.E.N.O.,” a revelation and a flat joke all in one. Similarly, J’s freestyles in Awkward Black Girl tended to acknowledge the diaristic intimacy of rapping while also deriding it. In one episode, when J drives around bumping the Doublemint Twins, the joke is that the overly literal lyrics mirror her life. “I’m in love with two n***as and they friends with each other,” Rae raps over her own voice, basic but above it at the same time.

Insecure refines Rae’s relationship to rap, cutting the campy distance down to naked, vulnerable self-expression. This is clear from the first episode, where Issa performs at an open mic, turning her forgotten birthday into a moment of triumph. Freestyling over Kelis’ stunt anthem “Bossy,” Issa wows the crowd with rhymes about broken pussy. “Maybe it’s really rough, maybe it’s had enough, broken pussy,” she says boldly, following a mumbled start. Afterward, still riding high off that spontaneous performance, she absconds with an old flame, the most daring choice she’s made in years, all because of rap.

As the series progresses, she continues to turn to rap to shake off her constant indecision, always confronting herself in mirrors. These mirrors are a distillation of that open mic, a head-to-head confrontation between who Issa wants to be versus who she is. Earl Sweatshirt once used the phrase “mirror raps” to describe raps for “when you’re getting ready to go to school. Raps you’re trying to say in the damn mirror.” The Samiyam song “Mirror,” which Earl originally intended to include on his second album, brings this idea to life. “Look at the mirror and what do I see?” Earl ponders. “Only the nigga I wanted to be/When I was in rehab,” he concludes, suddenly self-assured. Insecure doesn’t move as fast; it tends to loiter in this boundary between potential and reality instead of closing it.

On some occasions when Issa looks in the mirror, she sees too many people she wants to be. In one scene, instead of rapping in the mirror, Issa holds a fantastical conversation with her old flame and Ty Dolla $ign. It’s played for laughs, but really it’s disorienting, Issa’s mind ripped asunder rather than stabilized. The sudden appearance of her best friend Molly restores calm, but Issa’s relationships to mirrors never quite recovers. The next time she raps she’s in a vocal booth, being encouraged by her old flame, fully confident, no mirrors in sight. Following a decision to commit infidelity, she ends up in front of another mirror, facing who she wanted be in the flesh rather than in the abstract. She doesn’t like what she sees.

Ultimately, Issa isn’t defined by rap — she has an array of quirks and interests that characterize her beyond rhyming, plus the show’s soundtrack and score feature R&B, soul, funk, and electronic music just as much as rap — but her relationship with the genre gets to the heart of how rap bolsters and splinters the ego, particularly for black women. Issa uses rap to imagine and sometimes become alternative selves, for better and for worse.

Joan Morgan, former journalist and author of the essay collection When Chickenheads Come Home To Roost, once questioned whether there was a healthy space for women in hip-hop. Insecure couldn’t exist without the answer to that question being a resounding yes — it was also yes in 1999, when the book was published, by the way. But it goes further by honing in on the awkwardness of the fit, for women, and for men. For instance, Issa’s best friend Molly is the bold, assertive woman that we idolize in the abstract, yet she finds herself unhappy in relationships, often a product of men not really wanting an independent woman. Rapping in private was a joke on ABG, but on Insecure it’s possibility incarnate.

Stephen Kearse is a writer living in Washington D.C., follow him here.