It’s a Friday afternoon in late August, and Issa Rae—the
creator, star and executive producer of HBO’s Insecure—is
leaving the bar at The London hotel in midtown Manhattan.
But before she can make her way back to her room, a nervous
woman stops her. Apologizing, the woman says that she never
asks celebrities for photos, but on this particular occasion,
felt compelled to make the effort.
A few moments later, after Rae has obliged the selfie request
with a wide grin and left to get ready for a party for Insecure’s
Season 2 soundtrack, the woman explains: Rae, she says, is “a
hero for women 25 and up with melanin.”
Rae, 32, didn’t find this kind of recognition overnight.
Sure, she created a beloved YouTube show in 2011 that was
viewed by millions (Awkward Black Girl), landed a deal
with ABC and Shondaland in 2012 (the network
eventually passed on her show, I Hate L.A. Dudes)
and in 2015, published a New York Times
best-selling memoir (The Misadventures of
Awkward Black Girl). But she’s also dealt with
development hell: while with ABC, Rae says,
she was unsure of the story she wanted to tell
and overly eager to please executives, leading
to “a mushy, generic script.”
After the ABC deal ended, HBO called Rae to
tell her they liked her YouTube show and wanted her
to pitch something in that vein. She did, creating Insecure,
a half-hour comedy that follows “Issa Dee” and her best
friend Molly (actress Yvonne Orji) as they deal with dating
and job struggles in Los Angeles. HBO ordered a pilot in
February 2015, and the series premiered in October 2016.
The response was huge. Insecure became a critical
darling, landing Rae a Golden Globe nomination and drawing
famous fans like Oprah Winfrey and Michelle Obama. And
HBO clearly wants to see it succeed: this summer, the network
put Insecure in the time slot directly after Game of Thrones,
boosting the show’s audience to 1.3 million viewers in August.
Rae hasn’t become complacent, though, spouting off a
long list of things she still wants to accomplish. “I want to

be able to create movies. I want a television channel. I want

a studio. I want various media arms. I want to have political

influence,” she says. “I want to do so many different things.

I want to figure out how and the best way to use my voice.”

People are certainly listening. A few weeks later, during a

red carpet interview at the Emmy Awards, Rae said that she was

“rooting for everybody black.” The comment made headlines,

inspired a New York Times op-ed and was emblazoned on

T-shirts. And when news came out that she had inked a deal

with CoverGirl, her fans cheered her on.

“To be a CoverGirl is something I never thought possible,”

Rae explains via e-mail after the deal is announced. “Only in

my adult life have I learned to be comfortable in my skin, so if

I, as an ‘awkward black girl,’ can become [a CoverGirl],

it sends the message that anyone who is feeling

insecure in their own skin can and should be

celebrated as well.”

With that kind of hyper-awareness, it’s easy

to see why Rae would be chosen to champion

a brand like CoverGirl, especially as the brand

is looking to be more inclusive and reflective of

its consumers in its marketing.

“I really identified with their new branding: ‘I

am what I make up,’” Rae says. “As a creative who

has built her career from the ground up, those words

really resonated with me.”

Rae doesn’t have to build everything for herself anymore.

Nowadays, it’s Hollywood that’s courting her. In August, she

starred in the music video for Jay-Z’s “Moonlight.” She also

landed her first major film role (in an adaptation of the best-

selling YA novel The Hate U Give) and is penning a few scripts,

including one for a Netflix movie set to be directed by Ava

DuVernay and starring Rihanna and Lupita Nyong’o.

“My career started because I had something to say about

what I wasn’t seeing,” Rae says. “Me vocalizing what I wanted

to see, it basically changed my life and I’d say even the course

of representation indirectly. And I want to see what else I can

do just by speaking up and speaking out.”

ISSA

RAE

19

BY KRISTINA MONLLOS