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Did y’all know that “Insecure” was the first comedy in HBO’s over 40-year history created by and starring a Black woman?

Issa Rae June 2021 Vanity Fair Cover Story

Source: Adrienne Raquel / Vanity Fair

It’s only right that as the show’s fifth and final season approaches, Issa Rae is getting all the praise she deserves. She’s on the cover of the June 2021 issue of Vanity Fair — and honestly it’s one of the best features we’ve read on her to date!

One of the highlights for us is when Issa spoke to VF about “one of her biggest regrets.”

She talks about the time she rubbed Lauren London the wrong way by mentioning in interviews and in her memoir that a TV exec once suggested Lauren London would be a good fit to play the lead in a cable version of her “Awkward Black Girl” web series.

“One of my biggest regrets, naming her,” Issa says. “She took offense to that.” She goes on to reveal that she and London eventually made peace at Diddy’s legendary 50th birthday party two years ago, with help from London’s partner, Nipsey Hussle.

“He was like, ‘You should just talk to her. Let me set it up,’ ” she says. “It actually sparked an amazing two-hour conversation. We had so much in common. She was like, ‘People don’t understand, I’m an awkward Black girl.’ In the same way that I was upset about the limited portrayal of Black women, she was like, ‘People do the same thing to me.’ I completely get that.”

We’re glad they were able to work it out — and that we got another great Nip story! His presence is still felt in SO many ways.

On the “Insecure” side, Issa also talks about how she has been putting season-one pressure on the show while working on the final season, adding that she’s been rewatching from the beginning:

“All these memories come up, so I can’t watch it purely objectively. And then, of course, you look at performance stuff, you look at hair stuff, you look at appearance stuff. You’re just like, Okay, wow, I went on TV like that?”

Come on now! She didn’t look that bad — but you can definitely tell the wardrobe and glam wardrobe went up.

Issa Rae June 2021 Vanity Fair Cover Story

Source: Adrienne Raquel / Vanity Fair

For fans looking for hints about what to expect from the upcoming final season Rae says the last three episodes of the series should feel like a cohesive triptych, and the fact that the episodes are being filmed out of order this year makes it even harder for her to track the season’s arcs as she watches incoming cuts.

“I don’t know if it’s because it’s not complete, but I’m like, Is this”—she comically grits her teeth and lowers her voice—“not good?”

Issa also reveals that ending the show after five seasons has always been her intention and that she plans to NEVER write and act in a show she’s created again:

“Girl, no! I’m never doing this again,” she says. “Before you asked that question, I told myself I would never write and be in a show that I created again. It takes up a lot of your life, and I like to do a lot of things.” Rae slows her cadence, choosing her words carefully. “I love doing this show. I’m so grateful to be able to do this show. But that’s just not really for me.”

The issue also talks about Rae’s upcoming productions, which include “Sweet Life,” a docuseries about Black 20-somethings living in Baldwin Hills, inspired by the 2007 BET series Baldwin Hills, which she loved. She is also producing an adaptation of Nice White Parents, a podcast about a public school in Brooklyn alongside Adam McKay and she’s writing, producing, and starring in Perfect Strangers, based on the Italian dramedy Perfutti sconosciuti, about a group of friends learning each other’s darkest secrets during a chaotic dinner party. She also executive produces “A Black Lady Sketch Show” the Emmy-nominated HBO series that is currently in its second season.

Vanity Fair also broke the news in this story that Issa Rae is also working on a revival of Matt Damon and Ben Affleck’s HBO docuseries Project Greenlight.

“I want this version of the show to make filmmaking feel attainable,” Issa Rae says.

Listen, even without “Project Greenlight,” Issa Rae has done an incredible job of making Hollywood seem so much more accessible for so many black creatives.

She’s a queen for sure!

You can read the full Vanity Fair story HERE

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