The end of an era is really just the beginning for Issa Rae.
In an interview for TODAY’s first digital cover story, Rae said what she’s most proud of in creating and starring in HBO’s Emmy-winning series “Insecure” is its legacy. Rae said throughout the series and since it ended earlier this year, “Insecure” changed career trajectories for everyone involved.
“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,” Rae said. “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.”
The legacy of “Insecure” helped pave the way for what Rae, 37, is currently working on just six months after the iconic show ended with three new Emmy nominations in addition to the 11 it had before this year.
Rae’s sophomore show “Rap Sh!t” premieres on HBO July 21 and she is producing multiple projects through her companies, Hoorae and Raedio, plus starring in movies and writing some of her own.
The miniseries set in Miami follows two estranged high school friends as they try to become a hot rap duo. Rae said she’s always wanted to have a rap-centered show, and almost took “Insecure” down that path but compromised with just doing Mirror Issa. But she resurfaced the goal when HBO asked her what she wanted to do after “Insecure.”
“Thinking about this time in music, it just feels different,” Rae says. “There’s so many women rappers who are killing it. There are beefs here and there, but for the most part they all seem to be having a good time. They support each other, and that world felt interesting to me. So I just started thinking about the music industry and what the come up would look like, and the come up specifically through the lens of the internet.”
In this project, Rae included someone from her “Insecure” family. Syreeta Singleton got her start in the industry five years ago as a writing assistant on “Insecure.” Now Singleton is the showrunner for “Rap Sh!t.”
Rae’s production company, Hoorae Productions, produces two HBO shows: “Sweet Life,” which she created and executive produces, plus Emmy-winning “A Black Lady Sketch Show,” created by her friend and colleague Robin Thede. The sketch show just received five new Emmy nominations.
Thede told TODAY in an interview her show only ended up at HBO because of Rae.
Thede said her talk show on BET, “The Rundown with Robin Thede” had just gotten cancelled in 2017 when she got a phone call from Rae.
“Issa called me immediately, and was like: ‘Congratulations. Now, what are we doing together'” Thede recalled Rae asking her. Thede remembers being sad over losing her show, but Rae didn’t let her become discouraged.
“She was like, ‘I don’t care. Now we have an opportunity to work together because you’re actually free and you’re never free.'”
Thede told Rae she had a sketch show she wanted to do and a network already picked up, “but the money wasn’t right,” Thede said.
Thede remembered telling Rae, “I want it to look really amazing and I was set on creating the most beautiful sketch show ever. So she was like, ‘bring it to HBO.’ We went and met with them, and they bought it on the spot.”
“A Black Lady Sketch Show” premiered Season One in August 2019 and the following year, Rae launched Hoorae in September and started producing the show as of Season Two.
Raedio is Rae’s audio production company and record label she founded in 2019 in partnership with Atlantic Records. The company does music supervision, audio publishing, podcasts and events, among other projects.
As of last November, the company has signed four artists and won two Webbys for the series “Looking for LaToya.” More than 100 of Raedio’s productions have been featured in shows, such as “And Just Like That…,” “Power Book III: Raising Kanan” and “Sweet Life: Los Angeles.”
Benoni Tagoe, the president of Raedio, first met Rae when they worked together on her critically acclaimed web series “The Misadventures of Awkward Black Girl.” Tagoe said in an interview with Forbes last November that even while working on the web series, he and Rae discussed creating an audio company.
Tagoe said fans talked about the soundtrack to episodes of “Awkward Black Girl” and “Insecure” just as much as the show itself.
“Record labels recognized it was like striking the holy grail when an artist got a placement on the show, resulting in more streams and money,” Tagoe said. “That’s when we realized we were onto something. At that time we saw an opportunity to collaborate on the development of our label, Raedio, by combining her artistic expertise with my music industry experience.”
Starring in movies
Rae is starring in upcoming movie “Vengeance” premièring July 29 with Ashton Kutcher and B.J. Novak, who’s making his directorial debut with the film. The movie follows Ben Manalowitz (Novak), a journalist and podcaster who travels from New York to Texas to investigate the death of a woman he previously dated.
Rae is also in the new “Barbie” movie that’s currently filming and the team has been tightlipped about it. Rae said she was initially hesitant to join the sprawling cast, but the director, Greta Gerwig, won her over.
“I was like, ‘This sounds crazy, but OK. Let me just read the script,’” Rae remembered saying as a compromise. “When you read the script, you’re like, ‘Oh, I get it!’ It’s very funny, and it’s just very specific to her … working with her was absolutely amazing.”
Writing her own movies
Rae has already written her first movie screenplay and now it’s just a matter of starting production.
“It’s part of the next chapter. I’m looking to film one soon,” she said.
As for starring in her own movie, she’ll make that decision the same way she usually does: “I’ll see how that goes,” she said through laughter.