Issa Rae On Blackness, Representation and Creating Her Own Blueprint

By Sameer Rao Sep 05, 2018

With the third season of her hit comedy series "Insecure" now airing on HBO and several other projects under way, Issa Rae shines like the industry titan she is on the cover of Glamour magazine’s October issue. 

rntThe shoot accompanies a candid profile by The Shade Room founder Angelica Nwandu, which was published online yesterday (September 4). Rae reflects on the lifelong love of Black artistry that informed her projects, including "The Misadventures of Awkward Black Girl" and "Insecure." Here, three key excerpts: 

On challenging stereotypes and internalized doubt:

“You learn that a very specific type is appreciated,” she says. “For me, it was like, ‘If I want to pursue acting, I know that I am going to always have to be the best friend.’” In 2007, she graduated from Stanford University with a major in African and African American studies and a minor in political science.

An early web series she wrote satirized her experiences at the prestigious university, but it wasn’t until her popular 2011 YouTube series, "The Misadventures of Awkward Black Girl," that she put herself in a lead role. “The friend that I wanted wasn’t available,” she says. “I was like, Fuck it. I know how to act this part.” Still, she was uncertain about her future in entertainment. “The embarrassment came from making a YouTube series while all of my friends were being doctors, lawyers, diplomats, all of those different things. Those post-college questions—did I have to go to college to do this? Did I have to pay hundreds of thousands of dollars to make YouTube videos?—that was embarrassing for me.”

The self-doubt dissipated “when I started making the money back,” Rae says, so she leaned in to the image of the relatable (occasionally embarrassed, occasionally awkward) Black woman. Gone are the days of the video girl as the sole arbiter of our femininity. “There was no blueprint to do this. There was no one I could look to to be like, ‘Oh, so-and-so made some videos and then had a television show, and then did movies,’” she says. “You kind of just do it.”

On centering Black perspectives and voices:

Her characters on "Insecure" are real. They look cute, act wild and are unapologetically Black while doing it. They also live in a place where Black women live. As the backdrop on "Insecure," South L.A., and the gentrification that’s transforming it, looms large. “White people left the neighborhood, there was White flight, and now they’re coming back and pushing us out,” Rae says. “I’m moving back there—that’s what I want—but I’ve already seen the change. It’s disheartening.”

It’s the kind of gentrification she refuses to see happen to "Insecure." When I ask how she maintains her authenticity as the show continues to capture new viewers (62 percent of her audience is non-Black), Rae cites the benefits of “surrounding myself with people of color. I could never do this show and have a predominantly White staff,” she says.

On the blowback for creating a new show that stars Black LGBTQ characters:

Living at the intersection between art and commerce comes with other complications. There was the time Rae got dragged on Twitter after the announcement that she’s producing an HBO show called "Him or Her," based on the dating life of Black comedian Travon Free, who is bisexual. “Please don’t make that show,” one detractor wrote. “The Black community needs more visual representations of positive Black family dynamics.” The blowback was “really unfortunate because I love Black people, and I love everything that comes with us,” she says. “[Being queer] is the experience of lots of Black men, and it’s like, ‘Why would you try to prevent that story from being told? Who are you to tell him that his story isn’t valid?’”