Issa Rae opens up about being a Hollywood trailblazer

Issa Rae is on the cover of the latest issue of The Hollywood Reporter and she’s sharing some of the best lessons she got for navigating La La Land, including stop being polite; start kicking butt. Rae has become a trailblazer since pivoting her popular web series The Misadventures of an Awkward Black Girl into the Emmy-nominated Insecure, as well as about a dozen other projects in various states of pre-production and completion. There is nothing lowkey about how Rae is changing Hollywood for the better.Speaking to THR journalist Jessica Herndon, Rae says that her a-ha moment in the industry came five years ago when she was at a photoshoot for Essence. Rae was sharing the cover with an Avengers-level assembly of women in TV and film, including Ava DuVernay, Debbie Allen, Shonda Rhimes and Mara Brock Akil. At the time, Rae was still trying to find the right director to shoot the pilot for Insecure. The Hollywood legends shared stories from their careers and all gave similar advice–stop being polite and start standing your ground. Rae said the conversations, which she called a "life-changing moment," motivated her to let go of the director Rae felt wasn’t right for the show."Years later, he came up to me at a party and was like, 'Yeah, I would’ve f****ed your s**t up. You made the right choice,’” Rae told THR, who declined to name the director. “I felt so validated."The fourth season of Insecure premiered in April (you can stream all seasons on Crave) and brought in an average of 4.5 million viewers per episode  and earned eight Emmy nominations, including a Best Actress in a Comedy nom for Rae. Winning would make her just the second Black woman to take home an award in the category, which was first won by The Jeffersons’ star Isabel Sanford in 1981.[video_embed id='2001526']RELATED: Michael B. Jordan launches #ChangeHollywood initiative[/video_embed]Rae said she’s more excited for co-star Yvonne Orji, who received her first nomination for playing Rae’s best friend Molly on the dramedy. “Anybody can tell you when I heard Yvonne’s name, that’s when I got really excited. I had been nominated before, but I’m very much aware that I don’t do this by myself. I did feel guilty. It was just like, 'Everybody else is killing it and they’re really helping to elevate me and they’re not getting the recognition,’” said Rae. “But Yvonne was like, 'They’re watching and they’re seeing the work we’re doing.' To be a four-season show, to have it happen now, is not lost on me because there’s so many new and amazing shows. To have the culture support our show, it’s a FUBU [For Us, By Us] show in every way … I feel so blessed and we love every second.”

 

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Over its four seasons, Insecure has amassed a dedicated following, one that has continually demanded more and longer episodes, but Rae says that there were many times she thought the show would be cancelled before making it to air. Receiving push-back against her early drafts of the premiere season, Rae said she was devastated when Larry Wilmore, Insecure’s original showrunner, left to host The Nightly Show. Rae said the move ended up being one of the best things to happen to the series and helped it pivot away from being a workplace comedy.Still, Rae had to stand her ground at HBO, especially in rooms with mostly white, mostly male executives who didn’t necessarily understand a series about young Black women navigating friendship, work and love in Los Angeles.“I remember the biggest thing back and forth we had was with the former president [Michael Lombardo], and the show title. He wasn’t super insistent about it, but he was passionate about the fact that he didn’t think that Insecure fit because he was like, 'I see these strong, confident Black women, and they’re fierce.' And all the terms that we use to describe ourselves, but I was like, 'Ooh, that’s not … No, they’re not specifically.' And [that’s] exactly what we want to showcase throughout the show … the title reflects that, and as soon as I explained that that’s what we’re trying to combat, he got it and backed off.” Rae said that after the initial early days of Insecure, HBO execs gave her space to create the show she wanted to make and see.What many viewers see is a show that reflects the complexity and nuance of their lives in a way that few TV series have in the past. Season four of Insecure aired this spring at a time when the mainstream was having an awakening to the Black Lives Matter movement following the highly publicized killing of George Floyd. Coupled with the ongoing COVID pandemic, Rae said that she was unsure at first about releasing the new season in the spring of 2020.“We came on during a time when people were bored at home, and also there were racial uprisings, and our show served as a comfort. Thank God, because to release anything else during this time — even our show — I felt a huge guilt in coming out during the protests because there were just so many more important things happening, I didn’t want to take full focus away from that,” said Rae, who credits Insecure actor and writer Natasha Rothwell for sharing a beautifully succinct message about the series’ May 31 episode.“But to hear people be like, 'No, this is an escape. It brings us back to Black people being joyous and happy and ourselves' — our natural state really felt like we were meant to air during this time. I think that for sure helped people to see our show in a different light.”

 

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Insecure has been renewed for a fifth season and Rae is already busy working on episodes in a virtual writers' room. The prolific writer is also busy with several other projects, including running two production companies and a record label. She’s co-starring with Bette Midler, Sarah Paulson, Dan Levy and Kaitlyn Dever in the upcoming quarantine-filmed special Coastal Elites, which premieres Saturday, September 12 at 8ET on Crave in Canada.Rae is also teaming up with Jordan Peele for the adaptation Sinkhole, which tells the story of a couple who move into a home that has a literal sinkhole in the middle of it. Rae says that Leyna Krow, who wrote the original story, was excited for Rae and Peele to bring their own vision to the project. “[Krow] said in an interview what intrigued her the most was that the ideas that we had extended beyond her perspective. She was like, "I’m a writer and I think about white people when I write.' The idea that we could bring something else to the table in a way that she hadn’t thought of really excited her,” said Rae.“The premise is, basically, a couple moves into a house that has a sinkhole. When you drop things in it, the sinkhole makes everything perfect. The quest for female perfection is really intriguing to me and what that means now, especially in a culture that’s still resistant to feminism. There’s just something so eerie about that quest to me. Also, what Black female perfection looks like, and relationship politics—when you have a particular dynamic that’s working for you as a couple.”[video_embed id='2017129']BEFORE YOU GO: Air Canada promotes ‘leisure’ travel to U.S despite travel advisories[/video_embed]