Issa Rae covers Rolling Stone and talks Insecure's final season and her engagement

She says she's going to be the next Oprah or Denzel and TBH we believe her.
Published April 15, 2021 1:02 p.m. EST
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Issa Rae, who we can easily dub today's queen of television, is booked and busy, with the final season of her hit comedy series Insecure (stream now on Crave) on the way and a host of other projects in development. And in a gorgeous new cover story for Rolling Stone, she spilled all.

But first, let's list that resumé: In 2019, Rae became co-owner of a new Hilltop coffee shop in California, she owns hair-care company Sienna Naturals, has campaigns with Madewell, LinkedIn and American Express, and she owns Hoorae, a production company overseeing all of her film, television, music and events projects. *takes deep breath* 

According to Rolling Stone, Rae has around 22 movies and shows currently in development, while 16 alone are for HBO and HBO Max, whose parent company, WarnerMedia, signed a five-year deal with her for a rumoured massive nine figures. Say it with me: phew!

“I’m just always thinking about work,” Rae tells the magazine. “I was always like this. [In the past] it was like, ‘I need to work to make sure I have the means of affording a place to live.’ [Or] ‘This didn’t work, what’s the next thing I can do?’ I think that’s just how my mind works. That’s Capricorn shit. Workaholic shit.”

But Rae has big aspirations: to be as iconic as the likes of Denzel Washington, Cicely Tyson, Oprah.

“I want to belong here. I want to be among the greats,” she says. “I have to work to do that. It’s not enough to start things. These businesses and all these things that I’m touching still have to be great. Anybody can do this, but can they do it well? What I’m trying to prove is that I can do it well.”

Fun facts: she started early, writing her first spec script, for Cosby, at age 11, followed by another soon after of an original "high school dramedy." The rejection letters were swift.

Years later came Rae's popular YouTube series The Misadventures of an Awkward Black Girl, a mentorship under The Daily Show's Larry Wilmore, and soon enough the web-series was adapted for HBO into Insecure. The rest really is history.

Rae also briefly touched on her under-the-radar engagement to businessman Louis Diame, which she only previously acknowledged during the 2019 Essence cover shoot in which she revealed her ring.

“I just feel super-protective of any relationship I’m in,” Rae says. “That’s come from observing and making fun of people over the years who broadcast the most intimate parts of their relationships, then are left with egg on their face. I call them the ‘me and my boo’ people. Let me embarrass myself. Don’t let a n---- embarrass you. That’s always been my focus.”

As for Insecure's final season, all Rae offers is this: it won't touch on the COVID-19 pandemic at all and, instead, will play out like "a fantasy world" where parties and dining in still exist. And thank god for that.

To read the rest of the profile, click here and stream Insecure seasons 1-4 on Crave anytime.

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