Issa Rae Stuns On the Cover of Rolling Stone’s May Issue

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Issa Rae - Emily CottonTop
Credit: Rolling Stone

Since winning our hearts over with her popular web series Awkward Black Girl, Issa Rae has been on a roll. Not only has she created some much-needed positive representation of Black millennials with her hit TV series Insecure, but she has also secured a spot as one of the busiest women in entertainment.

Over the last few years, she’s inked an 8-figure deal with WarnerMedia; taught her own Masterclass to assist black creatives in navigating the business side of things; acquired a natural hair-care brand; and even created a whole new series while bringing Insecure into its series finale. 

Needless to say, the writer, actress, and entrepreneur does everything but shy away from hard work. And in her recent sit down with Rolling Stone, she details what her life has been like since she stepped onto the scene, additional works she has in store, and what she hopes her legacy will be. 

Check out a few snippets from Issa’s interview below: 

Issa Rae for Rolling Stone - Emily CottonTop
Credit: Rolling Stone

Issa on finding a sense of normalcy in being busy:

“I’m just always thinking about work. 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 sh-t. Workaholic sh-t.”

On keeping in touch with friends despite being busy during the pandemic:

“I’ve fallen short because I’m so used to [them] accommodating this in-person dynamic. So this year has tested who I am as a friend and really made me realize, ‘Oh, I’m not considerate in this way, and I can do more here.’ ”

On what Issa wants her legacy to be: 

“I feel like I have a cute story, but I want to be more than that. I want to belong here. I want to be among the greats. [Like] Denzel Washington, Cicely Tyson, Oprah…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.”

On the intimacy of her first autobiography:

“It felt like I was writing journal entries. The 24- through 27-year-old version of me will live on through a book. My opinions, whatever whimsical thoughts and notions, will live on forever. That’s what I don’t like about it. In writing a new book, I would focus on less of my personal life. My family didn’t ask for that. My aunt opening that book was like, ‘What the f-ck, girl? I was trying to read and support my niece and I’m in this.’”

On keeping her engagement to businessman, Louis Dame, a secret: 

“I just feel super-protective of any relationship I’m in. That comes 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 [man] embarrass you. That’s always been my focus.”

On experiencing gentrification: 

“I want to be able to look back and be like, ‘Aw, man. Remember when Inglewood used to be black?’ Watching so much of [Los Angeles] change and people be disregarded … Leimert Park is fighting so hard to stay black-owned. Those things really affect me. [My journey is] shaped by working in these white spaces and watching white people dictate what’s best for black people. 

Read the rest of Rolling Stone’s interview with Issa Rae here. 

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