Bossip Video

Another day, another Issa slay.

Issa Rae is covering Rolling Stone’s latest cover and in it, the 36-year-old writer-actor-producer is opening up about her childhood, the stresses of being a boss, and her growing business empire — including her record label and a new five-year [reportedly EIGHT-FIGURE] deal with Warner Media.

Issa Rae x Rolling Stone

Source: Dana Scruggs / Rolling Stone

Issa chatted with Rolling Stone senior writer Brittany Spanos and as expected they also discussed “Insecure” and its cultural significance as it prepares for its final hella hysteria causing season. Rae also told Spanos about her forthcoming series “Rap Sh*t” that’s co-produced by City Girls.

Unbeknownst to many, Issa said that the show that details childhood best friends who reunite to chase rap stardom was partly inspired by Jermaine Dupri criticizing female rappers for “only talking about their p***y.”

“I was just like, ‘This is so unfair.’ So that inspired the writing of it,” Issa told Rolling Stone.

“Unfair” is the right word, PERIODT. What do you think about JD’s comments partly inspiring Issa’s new series? We’re definitely interested to meet the two lead characters loosely inspired by J.T. and Caresha.


At one point in the interview, Issa’s fiancé Louis Diame [remember him?] is seen by writer Brittany Spanos—or at least Brittany thinks it’s Louis, but she’s unsure because she’s never introduced to the man who quietly hangs out in the background. According to Issa, she’ll never be a “me and my boo” person.


Issa Rae x Rolling Stone

Source: Dana Scruggs / Rolling Stone

A man I assume is Diame (Rae doesn’t introduce us) appears briefly at the couple’s home the first day we meet; masked in the presence of a rare pandemic house guest, he waves hello and shows off his “We Need Journalists” hoodie before disappearing. Later that week, when I join Rae for her early-morning stroll, he stays on the opposite side of the street, keeping the pace and minding his business.

“I just feel superprotective of any relationship I’m in. 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.”

“I know how I am as a consumer, as a stan of people, and what I look for. I had the foresight to shield myself from what anybody who was looking for anything on me would try to find, because I know this culture. Internet culture is so weird and malicious. I’ve just worked really hard to protect myself from the ugliest parts of it.”


We can respect that for sure. Protect yourself Issa, the Internet streets are indeed (so)nasty and (so) rude.


See more Issa Rae x Rolling Stone excerpts below.

On her work ethic and career goals:

“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 shit. Workaholic shit.”

“I have a cute story, but I want to be more than that. I want to belong here. I want to be more than an inspirational story. I want to be among the greats. 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 her mistakes as a young professional:

The first script she wrote after watching Gina Prince-Bythewood’s debut was submitted as part of her application to an ABC writers program. “My mom drove me because I missed the postmark deadline,” Rae recalls. “I put the little envelope under the door and then I got feedback a couple months later.” The response wasn’t what she wanted. “[It] was basically like, ‘This is laced with profanity,’” she says, laughing harder now. “Like, it’s ABC! What was I thinking?”

“The 24- through 27-year-old version of me will live on through a book [The Misadventures of Awkward Black Girl, her 2015 book of personal essays]. 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 definitely focus on less of my personal life. My family didn’t ask for that. My aunt opening that book was like, ‘What the fuck, girl? I was trying to read and support my niece and I’m in this.’”


Issa Rae x Rolling Stone

Source: Dana Scruggs / Rolling Stone



Issa Rae, photographed in Los Angeles on March 14th, 2021, by Dana Scruggs

Hair by Nicky B. Makeup by Joanna Simkin at the Wall Group. Styling by Jason Rembert

Cover: Bodysuit by Vex. Jewelry by Pamela Love

Interior: Dress by Monot. Earrings by Lady Grey


See Issa’s Rolling Stone cover story in full HERE.




Bossip Comment Policy
Please read our Comment Policy before commenting.