Issa Rae Might Be A Bit Too Smart For Hollywood

There was a time when Issa Rae actually read the random emails that came through her website’s contact form. I know because in 2011, I sent her a message in a bottle with only a castaway’s hope that she’d get it: “I’d love to do a story on you and your work.”

At that point, Rae’s work was still very much in progress. She was 26 years old. She wasn’t a name (not even one to get wrong) — yet. But her momentum was undeniable to anyone watching.

While an undergrad at Stanford in the 2000s, Rae had created a mock reality show about being Black at the university titled “Dorm Diaries.” It was a grainy yet cloudless preview of the kinds of stories she wanted to tell: punchy and particular. Then, after a few years of hustling, studying film and toying with the idea of law school, Rae engineered her big break in 2011 with the YouTube series “The Mis-Adventures of Awkward Black Girl.”

“ABG” landed at the base camp of peak TV. The early 2010s gave us genre-defining phenomena like “The Walking Dead,” “Game of Thrones,” and “Girls.” But “ABG,” by chronicling the minutiae of a young Black woman without an “S” on her chest (for “sidekick” or “super”), did something new by leaning into specificity without apology. It wasn’t an everywoman story, or even every Black woman’s story — because that’s impossible. But that didn’t mean it wasn’t for everyone.

For me, watching Rae as “J” didn’t feel like gazing into a mirror so much as a magnifying glass. J was the kind of girl I’d give a silent nod to as I passed her in the hallway. I didn’t know much about her, just that her world was vast yet invisible. Getting inside J’s head — inside Rae’s — was addictive; the only antidote was more. How did this 26-year-old do it? Where would she aim her lens next? I wrote a quick pitch and hit send.

Rae responded three hours later: “Please let me know what you need from me and I’m down :-).”

That’s the not-so-secret secret to Rae’s success, on HBO, the big screen and beyond. The woman is always down. She stays ready. She proved that recently, when she hit a hurdle in her race to the top. When it looked like Hollywood might not be the place for her stories after all.

After responding to my email, Rae and I spoke on the phone for an hour, and I wrote one of the first features on her. I knew immediately that she would do something big with the stories she’d been coming up with in the shower.

We stayed occasional pen pals over the next decade. When I was an editor at a now-defunct online women’s magazine, she wrote the occasional essay for me and even deigned to fill out a ridiculous questionnaire that included the prompt, “I Have Faked An Orgasm (Yes/No).” Rae’s answer: “Yes, oh God, yes. Mmm, yes yes, y-y-y-y-YES!!!!!!!!!!”

When it was announced in 2013 that she’d be working on a pilot called “I Hate L.A. Dudes” with Shonda Rhimes, I sent an all-caps congratulations email. ABC eventually passed. I was in the audience at Sixth & I Synagogue in D.C. when she read from her 2015 memoir and she told us about the pilot she was shooting about “me and friend.” “Insecure” debuted on HBO the next year and would, like her web series, steadily gain steam until it became a cultural locomotive.

No matter what “the industry” is up to, Rae is down. She’s remained centered on the mission to reveal the characters already starring in their own timelines, whether it’s in View Park, Baldwin Hills or Little Haiti. That’s what lead to the wildly popular “Insecure,” the bingeable “Sweet Life: Los Angeles” and the gone-too-soon “Rap Sh!t.”

That last one really got me. “Rap Sh!t” was top-shelf world-building from Rae. The Max show existed in the same universe as “ABG” and “Insecure,” even as its main characters appeared to be from a different planet. Trust we live in a world where Issa and Molly, semi-bougie L.A. girls who went to Stanford, would most definitely cross paths with Shawna and Mia, two Miami rap chicks whose manager does a little pimping on the side.

The hustle was strong on “Rap Sh!t,” which follows Shawna and Mia as they navigate the hip-hop world as a nascent rap group, learning the hard way who loses when you’re determined to see yourself win. Shawna (Aida Osman) is all heart, with freestyles as sincere as diary entries, while Mia (real-life rapper KaMillion) is all heat, a woman on a mission to make it happen.

But throughout the show, Rae was clearly asking herself the same questions Shawna and Mia were. Should they compromise? Go independent? Take the deal, get the bag and then circle back to the block?

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In 2021, Rae signed a five-year overall deal with WarnerMedia, Max’s parent company. Her reality show, “The Sweet Life: Los Angeles” was canceled in 2022 after two seasons, and “A Black Lady Sketch Show,” which Rae executive produced, was axed last summer after four seasons and as many Emmy nominations.

Max announced last month that it was canceling “Rap Sh!t” after two seasons. Fans of the show weren’t just upset but ready for a revolution, accusing the company now called Warner Bros. Discovery and the industry writ large of DEI fatigue and strangling Black shows before they’d had a chance to breathe.

This week, Rae remained characteristically outspoken about the trend.

“You’re seeing so many Black shows get canceled, you’re seeing so many executives — especially on the DEI [diversity, equity and inclusion] side — get canned. You’re seeing very clearly now that our stories are less of a priority,” Rae, who appears in the Oscar-nominated “American Fiction,” said in an interview with Porter magazine.

She sharpened the point even further in an interview with Time this week: “I’ve never seen Hollywood this scared and clueless, and at the mercy of Wall Street.” But as the magazine underscored, Rae is still down. She’s still out here hustling.

Rae’s working on two shows (one in which she will star) for HBO. Her company, Hoorae Media, has its hands in production, marketing, management and music. Not to mention her California coffee shops, line of hair-care products, and prosecco. And if that weren’t enough, Rae is also bidding on land in her stomping grounds of South L.A. on which to build a production studio. Cancel some shows? Fine. She’ll make more.

It all reminds me of the first piece Rae wrote for me in 2012. The essay was about the online hate Rae received after “The Mis-Adventures of Awkward Black Girl” won a Shorty Award for best web show. Haters came out to call her everything but a child of God. It got ugly.

“The bewilderment that our show not only exists, but that it could actually be good is indicative of how mainstream media thinks. I’m pretty sure none of the people tweeting that I’d only get three-fifths of my award had even seen an episode of our show, but they were 100 percent positive that it couldn’t be as good as whatever it is someone who didn’t look like me produced,” she wrote. “This mind-set is exactly why creative shows of color don’t get to exist on television anymore. There’s an overbearing sense of entitlement that refuses to allow shows of color to thrive. How dare we even try?”

I spotted Rae last summer in Miami at the American Black Film Festival. She was rushing into the screening of “They Cloned Tyrone” and I waved from my side of the red carpet, doing the thing where you introduce yourself real quick just in case someone doesn’t remember you. “Helena! Girl, I know who you are!”

On the same trip, I sat down with actress Gabrielle Union, who’s also carved her own lane in Hollywood by producing her own projects. When I asked where the permission to drive your own career came from, Union’s answer was quick — Issa.

“Issa was like, ‘I’m rooting for everybody Black,’” recalled Union, and instead of Hollywood snatching back her membership card she continued to thrive. “Oh wait, she just got more for loving us unapologetically and centering us in everything that she does,” Union said. “You guys, it’s okay.”

Is that a message for us, too? That even when Rae hits a snag, she’s still pushing uphill? In some ways you hate to see it: a creative mind having to constantly prove that its output is worthy of not just praise but patience. But she’s down for the work, and Union’s point was a necessary reminder. It’s okay. Issa’s got us.

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