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Today shared their first-ever digital cover story with none other than media mogul in the making, Jo-Issa Rae Diop—or as we all know her—Issa Rae. The feature deep-dived into Issa’s career trajectory from her Awkward Black Girl YouTube series to blessing our lazy Sundays with the hit HBO show Insecure and beyond. Journalist Sylvia Obell spoke to Rae about her personal life a bit, her latest TV endeavors, and where she sees herself next. They also discussed the parallel characteristics we see in “real-life” Issa and her self-titled character from her inaugural HBO series.
Rae, who deems herself a private person when it comes to her life, did open up about a few things that many may not have been aware of. As many of us only see the Issa Rae through her scripts and productions, outside of traditional Hollywood star ventures, she wants more for herself. The 37-year-old said, “I 100% want to do more outside of the traditional industry. But I want to kill it in this industry first.”
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And she is most definitely killing it already.
One of the most applaudable traits about Issa Rae’s self-titled character in Insecure was her ability to not only want more for herself, her loved ones, and her beloved city, but also to see it through. In reality, Issa’s real-life ambitions aren’t too far from what we saw on TV. The actress has given opportunities to first-time actors and actresses and put on blossoming artists’ music through Insecure’s seasonal playlists. The boss lady also has her hands in many business and philanthropic ventures.
“When people are like, ‘I started on Insecure — that’s so special, whether they’re writers, costume designers, cinematographers or directors,” Rae told Today. “Being able to let people hone their skills on ‘Insecure,’ and then watch them show and prove to the point where they’re now demanded by other projects … that’s dope to me, because I saw that happen on Black TV shows growing up.”
She added, “You start to build a foundation: a group of people that you’ve come up with, and we are the ones giving each other our second chances, and our third jobs, and then our fourth jobs. And they, in turn, are doing the same thing with their extended group of people. I think it’s a mentality that’ll lead to another shift of us looking out for each other.”
Rae has helped launch the acting careers of Insecure co-stars Yvonne Orji and Sarunas J. Jackson, and shed more light on newly married Jay Ellis, who has recently starred in Top Gun: Maverick. Since the Emmy-nominated series’ final episode, Orji has starred in the film Vacation Friends while Jackson has since appeared in Hulu’s Good Trouble, HBO Max’s Made for Love, and more.
Aside from her newly premiered Rap Sh*t HBO Max series, Rae has several movies on the way, including Vengeance (premiering on July 29) and a role in Greta Gerwig’s uncanny Barbie movie, which is currently filming. Rae has developed herself as not only a renowned storyteller but also a businesswoman. “It’s part of the next chapter. I’m looking to film one soon,” she said.
Speaking of business endeavors, the Inglewood native has her HOORAE production umbrella with a plethora of ventures underneath, such as the Emmy-winning A Black Lady Sketch Show and HBO Max’s reality show Sweet Life. She also owns the Hilltop coffee shop with businessmen Yonnie Hagos and Ajay Relan. Rae’s philanthropy spoke volumes in the HBO documentary Insecure: The End which showed her efforts to employ South L.A. natives with jobs such as security personnel, shuttle drivers, and more during the filming of Insecure. She even made plans to expand that work beyond a production set.
“I want to truly enter my mogul era, and that comes from empowering and building other moguls of color,” Rae revealed. “I think that’s my aspiration, and I just want to do it well. I want people and this industry, in particular, to take us seriously. I want to be a competitor with the best.”