Issa Rae has been "trying hard as fuck" to propel her brand of awkwardness from the internet to TV screens. Finally, five years after the debut of her web series The Mis-Adventures of Awkward Black Girl and a never-greenlit series I Hate LA Dudes, HBO is putting Issa's socially awkward life on full blast with Insecure, an eight-episode series that airs on Sunday nights.
Rae stars as Issa, a 29-year-old black woman who works for We Got Y'all, a nonprofit organization that mentors underprivileged children in south Los Angeles. She's the sole black employee, and is suspicious of her coworkers' "secret white meetings" and "secret white emails." Issa is equally hesitant about her relationship with her live-in boyfriend Lawrence (Jay Ellis), who is struggling to find employment after his startup failed.
Like her character J on Awkward Black Girl, Issa hilariously addresses how to overcome self-doubt, navigate dicey microaggressions in the workplace and deal with the agony of dating and relationships. She raps to herself, often in the mirror, to pump herself up before dealing with tense situations. In one scene she raps, "Do you know who you are? You da bossiest bitch. You a grown ass woman like Solange and sis."
And in one scene, Issa trades colorful lipsticks for new personas — bold shimmering pinks and even a matte black — before a night on the town with her BFF. It's in that relationship that the show really shines.
Insecure soars in its casual and effortless dialogue between two black girlfriends, Issa and her best friend Molly (Yvonne Orji). It is especially timely, as black girl squads on television are hard to come by, as Bene Viera wrote for Fusion in February. Mary Jane Paul (Being Mary Jane), Olivia Pope (Scandal), Annalise Keating (How to Get Away With Murder) and Rainbow Johnson (blackish), all leading ladies on their respective shows, lack black woman counterparts.
If Issa's character represents the "insecure," then Molly, a successful lawyer, could be seen as her confident partner-in-crime, except of course, when it comes to relationships. She has the most cringe-worthy interactions with her potential baes, where you'll want to scream at her in one moment, and commiserate with her in the next.
Molly and Issa trade quips just like any black girlfriend would at brunch. They dish on dating apps, old baes and casual sex.
"Sex right away, lose interest," Molly tells Issa about her troubles with dating. "Wait to have sex, lose interest. If I don't have sex at all ... motherfucker no, I'm a grown ass woman, I did not sign up for that bullshit."
"I think your pussy is broken," Issa snaps back.
Later, Issa says matter-of-factly, "I don't have time for the bullshit anymore," she said about her relationship with Lawrence. "I'm breaking up with him tonight."
"Bitch, no you not," Molly jabs back.
Insecure excels in what audiences of Awkward Black Girl once heralded by speaking for — and to — millions of black women. In recent interviews, however, Rae is quick to explain that Insecure is not an attempt to showcase a universal black experience, and that she is not the on-screen messenger for all young black Americans.
"I do feel a light annoyance that some people will project all of black women's experiences and woes on this show, and that's not what I set out to do," Rae told the Los Angeles Times. "People may think I have to be the definitive voice. I just wanted to share a very specific experience and hope that people see themselves in these characters."
Nods to blackness are effortlessly weaved throughout Insecure. The series begins with Kendrick Lamar's "Alright," as scenes of south Los Angeles — Randy's Donuts, a black hair supply store and Slauson Avenue — splash across the screen. Molly's dog is named Flavor Flav. In Issa and Lawrence's apartment, a Do the Right Thing poster hangs on the wall and a pillow sporting Nicki Minaj's face sits on the couch. Molly "skee-wees" her sorority sister at a house party, in a nod to the Alpha Kappa Alphas, a black sorority. "How Sway?" and "boy bye" and "bish, wheeett?" are sprinkled into the dialogue for good measure.
For Rae and her web series superfans, the show is also full of familiar faces. Her Issa Rae Productions family has not been left behind. Sujata Day (Cece from Awkward Black Girl) is one of Issa's shady coworkers. Tristen Winger, who portrays Thug Yoda, Issa and Lawrence's gang-banging neighbor, was once the whispering coworker Darius on the web series as well.
William Catlett (who starred in First, a web series that ran on Issa Rae's YouTube channel) is a "hotep n*gga" who Molly hooks up with just "because he was fine." There's Molly's Alpha Kappa Alpha sorority sister, Tiffany, portrayed by Amanda Seales, an actress and internet personality whose web series premiered on Rae's YouTube channel. Members of Dormtainment, an Los Angeles-based comedy group that has collaborated with Rae, also appear throughout the series. With these casting moves, Rae is using Insecure as a vehicle to amplify black talent in Hollywood and it is another subtle yet great strength.
That Issa Rae's show has made it to the small screen is a win for awkward black girls everywhere. Here's hoping that as creator and star of the show, she has found security in that.
Insecure airs on HBO on Sunday nights at 10:30 p.m. Eastern.