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Issa Rae: Woman In The Mirror

EBONY September 2018

Awkward. Insecure. Impulsive. These are some of the adjectives TV producer Issa Rae uses to self-describe, even though the 33-year-old’s impact on the television industry is clear: She’s the reigning impresario and vanguard of authentic Black voices.

It’s standing room only in the brightly lit church sanctuary. Sunlight streams through the stained glass windows, shining down on parishioners lucky enough to fill the pews. Yet in this context, “lucky” seems inappropriate. On the left is a poster of a young man. In the center, his open casket, white with a splash of color from the bouquet of flowers on top.

Bowed heads seem to send up prayers for yet another young Black life snuffed out before reaching the age of consent.

Painted above the chancel is the phrase “A Fellowship of Love.” Positioned underneath is the gospel choir poised to offer comfort through song. A woman dressed in a black business blazer and T-shirt with white letters that spell out “Just-Us for Justice” is at the lectern. Mourners turn in the direction of the speaker.

“Violence. Brutality. It’s the same story, just a different name,” the provocateur says.

The provocateur is Rae. The scene is from the upcoming 20th Century Fox film The Hate U Give.

Scheduled for release in October, The Hate U Give is based on the novel of the same name by Angie Thomas. It’s the story of a high school student drawn into activism in the aftermath of a tragedy.

Rae plays activist April Ofrah, who helps the film’s protagonist, Starr Carter (Amandla Stenberg), understand that her voice is the most powerful weapon available to her. In a case of art imitating life, Rae also found her voice as a teenager, during her freshman year at Stanford University when an older classmate cast her in what Rae calls a “hip-hopera.”

The first-time Emmy Award-nominated actress says the production ignited a passion for something she couldn’t define but loved. With a camera borrowed from the university library, her foray into television production kicked off with Dorm Diaries, a docuseries of campus life. The ensuing footage would reveal close-ups of Black students who thought like Rae, spoke like her, complained, loved, desired, feared—a range of emotions that moved a community, unlike the two-dimensional characters she’d seen in network TV programming.

Rae relied on the students featured in the show to tell their friends to watch the web series on YouTube. Also using social networking sites, including Facebook, she was able to reach other college students with the story of Black student life at a predominately White university.

“Then it just grew,” she says.

The growth spurt included Fly Guys Present The ‘F’ Word, two versions of The Misadventures of Awkward Black Girl (the book became a New York Times best-seller, the web series snagged a 2012 Shorty Award). Another web series, The Choir, followed.

Based on the success of her award-winning web series, the impresario got the opportunity to include a cable television show to her growing media empire. The New York Times reported that in December 2014, HBO Entertainment gave the green light to her script about two 20-something Black women and their misadventures in LA. Rae would become the first Black woman to create and star in a premium cable show when HBO ordered a series for Insecure in October 2015. The 30-minute comedy would make its debut one year later.

MIRROR BITCH

Insecure character Issa Dee looks directly into the camera and comes into focus like someone’s wiping a foggy bathroom mirror. In what has become a running gag for the show, she freestyles a few bars to the woman in the mirror she calls “Mirror Bitch.”

The theme that drives Insecure is sisterhood. “Two Black women who are there for each other through all the bullshit, through all their self-imposed bullshit that is put upon them but that bonds them,” Rae says.

There’s also the bond between Issa Dee and Issa Rae. One gets feedback and courage from the other to carry out her mission. The goal in real life, Rae says, is to bring more diverse stories to television network, cable and digital platforms. Stories such as Insecure that examine Black sisterhood.

“The ability to be vulnerable with your sisters and friends is so crucial and kind of outweighs the strong Black woman narrative. I’m not saying that’s a bad thing. It’s just you can’t be that all the time.”

Rae believes Black women should have the right to be vulnerable. “The narrative—you have to be the strong Black woman, don’t let them see you sweat, don’t ever let them see you cry”—is an unfair burden of expectation, she says. And she wonders why there isn’t a narrative that Black women can be weak.

She understands that the foundation of the strong Black woman archetype comes from observing Black women make a way out of no way and having a history of handling things, but it doesn’t hold true for all. And even if it were accurate, Rae says, “I’m more interested in the moments where we just don’t have it together because those are moments that kind of bond us, too, especially in sisterhood.”

Rae believes stories from underserved cultures and communities are compelling and breed understanding, tolerance and appreciation. Before interviewing writer and director Justin Simien for A Sip, the talk show produced by ColorCreative.TV and Issa Rae Productions, she found during her research that reviews for Dear White People elicited comments such as “I just didn’t understand” or “I’m getting a new perspective.”

“So to be able to have the opportunity to empower other voices that want to tell stories that we’ve been denied kind of all our lives is powerful to me,” she explains.

PEABODY AWARDS

Hasan Minhaj, comedian, senior correspondent of The Daily Show with Trevor Noah and host of the 77th Peabody Awards ceremony in May, found himself recognizing Rae’s newfound power to get the green light for projects from writers of color. Near the end of his introduction, he said, “Issa Rae is powerful. Issa Rae is hopefully open to my great idea for a script.”

No word yet on if Minhaj was successful, but his timing was perfect. The prolific producer, who was receiving the award for Insecure in the entertainment category, had several deals in the works from her HBO two-year first-look production deal announced in 2016. At press time, the network had approved three more Rae projects: Sweet Life, a story about affluent Black teens from Windsor Hills, California; Him or Her, a comedy about a bisexual man navigating dating life; and Turner House author Angela Flournoy’s untitled ’90s family drama. And there’s a fourth yet-to-be-named show under consideration.

Once again, Rae was positioned at a lectern. This time, however, she wasn’t alone. Jonathan Berry, of 3 Arts Entertainment; Prentice Penny, Insecure showrunner; Melina Matsoukas, director; Yvonne Orji, on-screen best friend; and Jay Ellis, on-screen boyfriend, stood with her.

She thanked each of them, then acknowledged the pioneers who paved the way for shows such as Insecure to make it to the airwaves: “Thanks to every single writer of color that has come before us that worked on a show that they didn’t want to be on, just so we’d have the opportunity today to tell and create our own stories.”

Larry Wilmore, host of Comedy Central’s The Nightly Show with Larry Wilmore, which aired from 2015 to 2016, who would become the series’ co-creator, is another veteran writer Rae credits for helping her make the transition to network television.

When HBO executives approached the Awkward Black Girl web series creator in 2013 for ideas, she was still new to television screenwriting.

Rae’s management, 3 Arts Entertainment, paired her with Wilmore, who is also represented by the same firm. The two immediately hit it off, and the iconic producer says Wilmore helped her honor her voice. Their work resulted in an original story the Peabody board of jurors lauded as “a series that authentically captures the lives of everyday young, black people in modern society.”

Ironically, the web series, Awkward Black Girl, that would lead to the award-winning HBO television show, Insecure, started as something else. Rae says after falling on hard times while living in New York, she came up with a different concept for the phrase.

I LOVE NEW YORK

Rae had had plans in the works to leave Los Angeles since high school. So with a $6,000 Public Theater fellowship in hand, she says, she left for New York City in 2007, one or two days after graduating from Stanford with a major in African and African-American studies and a minor in political science. “You’re going to hate it here. Don’t do it. It’s dirty,” warned an older brother who lived there and worked in investment banking.

“He had a great apartment, and that definitely wasn’t going to be my experience, but I still had such a love affair,” she says. Unfortunately, the Big Apple didn’t return her affection. Someone stole the tools of her trade—a laptop, camera, equipment, pitch reels and her scripts. During one of her journal-writing sessions, she started thinking of ways to earn extra cash. One of her ideas was to sell “Awkward Black Girl” T-shirts and create a comedic animated series to promote them. She shelved the idea and wouldn’t revisit it again for another two years.

Rae went back to LA for a cousin’s graduation and met up with friends for a beach day. Two of her friends were in the entertainment business; one was an agent trainee for Creative Arts Agency (CAA), the other was in the producing program at the University of Southern California.

“We were just sitting on the beach, and my agent friend from CAA was like, ‘Girl, why are you over there willingly struggling in New York?’” The agent trainee said she could make Dorm Diaries happen.

Rae convinced herself it wasn’t failing if she returned to LA. “It was going to be easier in LA, and I was broke. So why was I so determined to make it work?” She says one of the reasons she didn’t want to go back was because her friends were there. Rae grew up in Windsor Hills and didn’t want to get lost socializing. “So many people who are in LA just get caught up in the hustle of doing nothing. They’re maintaining. They’re floating. I know how easy it is just with the love I have for them.”

She returned to LA permanently in July 2009, but not before going to Dakar, Senegal, with her sister. “Even in Senegal, I was creating a web series … in French, and I was so excited to shoot that. Then, I lost all of the footage on my hard drive.” She returned home and hit the ground running, shooting her second web series, Fly Guys Present The ‘F’ Word, starring her brother Lamine.

College had not prepared Rae for this career. At Stanford, career paths are already charted, she says. If you’re in medicine, then you’ll be a great doctor, complete with the right connections. She says all her friends felt like they had a set path of success. But for a television program creator in new media arts, there was no map to help her navigate the uncharted territory.

WORK YOUR PASSION

The learning curve was steep. Thirteen years ago, YouTube was still in its infancy. Yet in 2007, Rae had the foresight to upload and star in videos such as Nani Pop, a freestyle rap performance shot in black and white, extolling the virtues of both having a punani and the skills to “pop the nani at the club.” Still, she says, “At the time, the internet was just seen as fluff.” Conventional wisdom was social networking sites such as Facebook, Twitter and My-space were places to tell jokes but not to create an actual show.

“I had to tell myself, ‘If you want this you’ll have to be disciplined. You must act like this: If you’re making a web series, you must make sure that it’s coming out at 10 a.m. every Monday—by any means necessary. If that means you’re canceling plans to work; if that means you’re missing Taco Tuesday; if that means you’re missing the wine down—you have to make your passion a job.’”

It was a job without money for a very long time, Rae acknowledges. During those times, she would battle self-doubt so that it would not crowd out her creative vision. “I hope [she] gets it together ’cause …,” her friends would say. But then, Rae says she would rein in her imagination and quickly snap out of it.

“I did have supportive friends. They’ve always made me feel like my work was good, and they’ve been in every single project I’ve produced. Whether that’s behind or in front of the scenes, they have been there. I credit them just for giving me the confidence to do it and giving me the space to do it.”

Today, Issa Rae Productions’ digital content is featured on YouTube to bring attention to up-and-coming writers of color. She keeps their shows flowing via programs such as #ShortFilmsSundays on platforms, including YouTube, where there are more than 350,000 subscribers; The Peak; ColorCreative.TV; and others. “We aim to do that the same way with independent music artists. Something I’m really excited to be able to do . . . is to use Insecure to . . . break new music from independent artists and people who otherwise wouldn’t have that opportunity. That comes from scouring SoundCloud accounts or getting recommendations and, of course, working with our brilliant music supervisor [Keir Lehman]. I think every platform I have is just about discovery and giving opportunities that aren’t readily available to us.”

FEAR OF HEIGHTS

There’s a maxim in journalism that you’re only as good as your last story. Rae says the same is true for television producers. So, to combat that fear of falling from a great height, she concedes to staying busy. “My defense mechanism [is] always having something else; I’m not putting my eggs in one basket. You are always creating because that’s also a joy. There’s nothing more exhilarating than having a new idea—an idea that’s just yours and that you feel like primed to develop … I have this new idea that I know is the shit. As long as I have those moments, I know I’ll be OK and I think that’s what powers me.”

And if ideas are the elixir of life, then the TV producer has created her own power plant at ColorCreative.TV. The platform is a virtual idea factory where Rae and Deniese Davis, producer (The Misadventures of Awkward Black Girl, Insecure, Netflix’s Burning Sands), work to discover, produce and sell content from women and writers of color.

In January, ColorCreative.TV won a grant from Pop Culture Collaborative, a project of Rockefeller Philanthropy Advisors, to help bring diverse storytelling to the media and entertainment industry. According to Pop Culture Collaborative’s website, the money is earmarked to assist ColorCreative.TV in its effort to become a company that offers an industry-leading pipeline to help writers of color secure jobs in the television and film industry.

Bringing diverse stories into the mainstream is the award-winning writer’s passion.

“I also prioritize telling those stories because I genuinely want to see them. I don’t know everything. I haven’t had every experience, so it’s just the curiosity and a genuine love for hearing about diverse experiences.” There are so many stories to tell, and Rae says she’s only scratching the surface. “We’ve been denied so much of our own history, like in the school system, [and it] kind of infuriates me. In the entire school system, you learn a very specific narrative and you’re kind of denied so many of the rich stories that we have just culturally and worldwide.”

NO DOOR? CREATE ONE

“90210 for Black kids,” Rae tosses out in her fantasy pitch on The New Yorker YouTube channel. “Main character would be Little Richie. He’s tired of the access and excess: ‘I’m so tired of being rich; there’s more to me than this.’”

Her expression of confidence changes to surprise when she realizes she just kicked a rhyme off the top of her head that could be used in the show’s theme song.

Rae pitches ideas like Mo’ne Davis, former Little League star, pitched fastballs, and she says she doesn’t want to be on the wrong side of a closed door again.

“It’s so frustrating to not be heard, and that’s what I felt like in terms of trying to pitch some of my ideas. The entry was so limited.” Rae recalls the time in 2010 when she tried to sell Dorm Diaries. She says the television executives were very dismissive. “There just weren’t a lot of opportunities, there weren’t a lot of Black stories being told and it just felt like they were looking for this one thing.” She was able to create her own doorway for opportunity with the available social platforms.

Today, she thinks only in terms of opening the door.

“It is amazing right now that Justin Simien, Lena Waithe [Emmy Award-winning writer, creator, The Chi], Ava [DuVernay, director, Selma, 13th]—all these other people—Donald Glover [Atlanta]—are now in the position to be able to usher in new talent.”

She believes this generation of Black Hollywood is genuinely interested in empowering other voices. “Now that the door is open, you best believe that I am [laughs]. My foot is in the door, my hands are in it, you’re going to have to smash my head through before you push me out.”

After talking on the phone with the star, it becomes clear: The woman in the mirror is the Issa who carries out the mission, and the Issa outside the mirror is the provocateur. Together, they make one hell of a team.

“The ability to be vulnerable with your sisters and friends is so crucial and kind of outweighs the strong Black woman narrative.”

photography: Brian Bowen Smith
creative direction: Courtney Walter
photo production: Bianca Grey
styling: Shiona Turini
makeup: Joanna Simpkin
hair: Felicia Featherwood