Insecure Black Women: A History

James Jones, Esq.
Jul 22, 2017 · 5 min read

Issa is back. We don’t know if she’s back with Lawrence or if she’s ditched Molly and become best friends with CeCe. But we do know that she’s back, and she’s more insecure than ever.

Today NPR aired an interview with Issa Rae on the creation of her hit HBO show “Insecure.” The host, Terry Gross, drew very similar comparisons to the characters Issa from “Insecure” and J from “The Misadventures of Awkward Black Girl.”

Rae told the host that insecure was another word for Awkward and she wanted to continue J’s awkwardness with Issa (paraphrased). On the importance of Issa and J, Rae said that Issa and J were the first mainstream black female TV characters to be awkward. In the interview, she goes on to explain segregated comedy and how the concept disallows black women characters to exist in that space.

I didn’t consistently watch a lot of white TV shows growing up. Most of those that I did watch from time to time were due to the cable being off or random channel surfing. For the most part, all the shows that I watched from pilot to series finale were black shows. Of those shows, four had awkward Black women as leads.

  1. Whitley Gilbert in A Different World: I know what you’re thinking, but re-think it. Whitley was awkward. She was alluring, she was beautiful, and she was rich. But none of that negates that she didn’t fit in with her surrounding. Southern bell, debutante, trophy wife in training lumped in with “first Negroes on my block” to go to college? Not easy. Because of her otherness, her awkwardness often came out in the form of a big personality. Whitley may have been high falutin, high yellow, and high strung. But she was plain old awkward and black.

2. Synclaire in Living Single: Yep, I surprised you again. Just because a characters is lovable and fits in with her circle of friends, doesn’t mean she’s not also awkward. I loved Synclaire. She brought a certain je ne sais laugh to the show and she could read and throw shade like she grew up in the House of LeBeija. Truly, it must be hard not being the most attractive (Regine), not being the most educated (Max), and not being the most successful (Khadijah). That difficulty led to a lot of awkwardness — and that’s what I liked about her character.

3. Mona from Half and Half: Oh, Mona Alone-a! I loved her. She was rocking platform boots and twist outs before the natural hair girls laid claim to it, and she was an attractive thickum. Something you don’t see regularly in 90s sitcoms. But for all of her perfection, her life was a big awkward mess. With Big Dee Dee constantly taking shots at her, Little Dee Dee always trying to out shine her, and her own father basically fuckboying her the whole series, it was hard for her not to have social hang ups. Mona was 25, had a huge and furnished bachelorette pad in expensive ass San Francisco, had potential best friend peen in Spencer, and was the Vice President of a record label. Banging right? Wrong. For all of these wins, Mona’s awkwardness caused a lot of Ls.

4. Joan from Girlfriends: The Queen B of Awkward Black Girl herself! Joan was loopy as hell. She didn’t fit in anywhere, and she didn’t have any real friends. William stiffed her for a promotion. Toni slapped the hell out of her after the Jamaica trip. Maya sicked her home grown thugs on her on several occasions. Lynn stole her identity, stole her health insurance, moved a bum into her house, and did a TV expose on how trashy her restaurant was. And what did Joan do? Give them all a place to stay, delicious baked goods, and wonderful holidays. Joan was just too awkward to stand up for herself. She even agreed to marry a man who was totally outside the plan she had for her life because it would have been too awkward for her to stand up and say she deserved an equally intelligent and upwardly mobile partner. Cancellation was Joan’s friend. It would have been too awkward to see her character debased any further.

So, maybe Issa is right. Perhaps her two characters are the first awkward black women in mainstream TV. And segregated comedy may have kept them out of the mainstream until now. But segregated comedy also allowed awkward black women to exist in black spaces where their awkwardness was not attached to their racial otherness. Maybe that made it less awkward for them and for us watching. So, salute the awkward black women of past segregated sitcoms and welcome the newly awkward black women of integrated TV. I’ll be watching season 2 of “Insecure” as Issa builds on the foundations laid by characters such as Whitley, Synclair, Mona, and Joan.

Oh, yeah. Bank Teller better be a main cast member this season. And bring back A! He was her one true love.

About me: I’m a lawyer in Atlanta. I develop & manage new artists. I blog. I tweet. I create and curate videos. And I’m a represented Film/TV script writer.

James Jones, Esq.

Written by

A writer living a double life as a family law attorney. Past College Language Assn short story Winner, Hurston/Wright new novelist, TV One Black List winner.

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