A Decade of Watching Issa Rae

As the groundbreaking HBO series Insecure comes to an end this week, Hanna Phifer reflects on ten formative years of Issa Rae's stardom.

hbo's final season premiere of "insecure"  red carpet
Amy SussmanGetty Images

It was 2011 and I was 16 years old listening to Frank Ocean’s “Thinking About You” on YouTube when my eyes landed on a comment underneath the video. “Like if Awkward Black Girl brought you here.” Who is Awkward Black Girl? I thought to myself. One Google search pointed me in the direction of a web series about J, a 20-something Black woman who attempts to navigate the cringe moments of being a Black woman in the corporate world, while also trying to find herself in the larger world that wants to pigeonhole her in stereotypes about Black womanhood. “I’m awkward and Black,” J says. “Someone once told me those were the two worst things anyone could be.”

I immediately became obsessed, bingeing the episodes that were available at the time in one sitting. It was biting and sharp in the ways that shows at the time like The Office and Curb Your Enthusiasm were. I remember the feelings of breathless laughter I had over the moments when J would express her frustrations by breaking out into a rap or all the references to '90s pop culture moments, like J stumbling down the stairs during her attempt at trying to re-create the famous scene from She’s All That. More than anything, however, what drew me into Rae’s awkward and cringe-inducing world was how much I could see myself in it.

If you were a Black girl, there were only so many options you had when looking to be represented

It can be difficult to remember, with the plethora of content dedicated to Black girlhood now, but back in the early 2000s to mid-2010s, if you were a Black girl, there were only so many options you had when looking to be represented in the media. You could be the combative and catty types who were depicted on “reality” television. You could be the sleek, professional, Michelle Obama type. You could be the best friend, the sidekick, the Black girl who provided sassy quips and nothing else. “Somewhere along the line, we became unrelatable and invisible to the Hollywood system,” Rae says in her personal essay collection, The Misadventures of Awkward Black Girl. “Our images and diverse portrayals just weren’t worth the dollars and effort anymore.”

At such a young age, I could already feel the constricting pressure of being a circle trying to fit into the square peg that was Hollywood’s idea of Black girlhood. I was painfully shy and depressed. The loneliness I felt at that time was only accentuated by my inability to see myself. That the feelings of perpetual out-of-placeness were so unique that no one could possibly know what it felt like to be me.

It feels like so much of my journey of growing into what Black womanhood could be has happened in tandem with Rae’s career. Since ending her successful web series, Rae has gone on to accomplish many things, including writing a book, hosting a talk show, starring in several films, starting a record label, and opening a coffee shop. Oh yeah, and, of course, there’s just that hit HBO series of hers.

What drew me into Rae’s awkward and cringe-inducing world was how much I could see myself in it.

My journey so far has not been nearly as punctuated with the many successes that Rae’s has. There have been many days that have culminated into years of me crying after high school ended, and even more so after I dropped out of college, feeling as if I was never going to escape the awkward feelings that have plagued me since my youth—that I was doomed to be forever misaligned with the rest of the world.

The fictionalized version of Issa in Insecure quits her comfortable nonprofit job and takes on odd jobs to make ends meet, like driving for Lyft and being a landlord, until she finds a passion that financially sustains her and makes her proud. I have gone through a similar bout of growing pains to come closer to a more secure version of myself. Taking a page from real-life Issa Rae’s life story, I’d begin using my talents as a writer to write myself a world when the one that existed was unwilling to make space for me.

After Insecure premiered in 2016, I felt a mixture of pride and protection as Rae soared into the spotlight. I have this feeling every time someone from the Internet makes it big. Perhaps it’s this one-sided sense of intimacy that is fostered whenever you see someone come into themselves whether creatively or personally in real time.

I’d begin using my talents as a writer to write myself a world

I feel cynicism now toward the ways Hollywood has preyed on our desire to see ourselves reflected onscreen. But my teenage self needed to know that there are Black girls who felt just as out of sync as I did, trying to navigate the boxes this world wants us to be in. There is a feeling that the English language has yet to capture, when someone extends a proverbial hand to guide you out of the depths of your own despair. When someone comes forward and makes you realize that all your oddities and quirks and—yes, awkwardness—are not as weird as you once thought they were. I can hear the ringing of the word parasocial in my ear whenever I talk about how much Issa Rae means to me, but what other options have I been given other than to beam with earnest affection when it comes to her?

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