Issa Rae on the Happy Shock of ‘Insecure’ Emmy Nods and Building the Hoorae Brand: ‘I Want to Have an Ecosystem’

On July 12, Issa Rae was in the middle of a meeting, largely unaware that Emmy nominations were being announced. Then she received a text from “A Black Lady Sketch Show” creator and star Robin Thede, congratulating her on being nominated for lead actress in a comedy.

“I had a little squeal that I let out in the meeting, and then kept it pushing, but I was happy,” Rae says.

And there was plenty to be happy about. In addition to her solo recognition, “Insecure” nabbed two other noms for editor Nena Erb and cinematographer Ava Berkofsky, plus “A Black Lady Sketch Show,” which Rae executive produces under her Hoorae multimedia banner alongside Thede, earned five nominations.

Despite two previous lead actress noms, Rae admits she was skeptical about being recognized this cycle, given that “Insecure” aired its fifth and final season in December 2021. But there wasn’t a ton of time for the typical champagne celebration, Rae had work to do. More specifically, she had to clock in for a shift at Hilltop Coffee + Kitchen in Inglewood, an establishment she co-owns, later that afternoon as part of the promotional push for her second HBO series, “Rap Sh!t.

“That was already in the works, but I was still happy to go,” Rae quips when asked about posing for selfies and serving up lattes as Issa the Barista. “People are just so generous, and I got so much love there, so it was just nice to be in my community, with my people, and then serving them.”

The next day, Rae did get her party on, posing on the pink carpet at the L.A. premiere of “Rap Sh!t.” With the stars of Rae’s “Sweet Life: Los Angeles” reality series — which returns for a second season on Aug. 4, airing in conjunction with “Rap Sh!t” — also in attendance, the event served as a physical manifestation of Rae’s creative expansion.

Dan Doperalski for Variety

What is it like to see Hoorae continue racking up Emmy noms?

That’s extremely exciting. To go from [calling Robin Thede] like, “Hey, girl, do you want to work together?” to HBO greenlighting the show, and then for it to be acknowledged in this way year after year, that’s super cool. Obviously, there’s a business element to it, but at the end of the day, it’s just like fan to fan, it just feels good to be able to put people on and then have other people fall in love with them in the same way that you are.

Syreeta Singleton is the showrunner of “Rap Sh!t” and alum of ColorCreative (the management arm Rae co-founded). Raedio, which is doing the music for “Rap Sh!t,” and Sienna Naturals [the natural hair care line Rae co-owns] was featured at EssenceFest. How are you feeling about the ability to have this synergy between the projects?

That was an intention that we set in 2020; I’ve just been really, really focused on making sure that the businesses are synergistic, and making sure that our department heads, our leaders, are looking out for one another. It is a challenge, but I want to have an ecosystem. This show, in particular, was our first opportunity to be like, “All right y’all, it’s all hands on deck. Let’s see what we can do and how we can be self-sustaining.”

You posted a video congratulating Thede, as well as shouting out “Abbott Elementary’s” Quinta Brunson. What does it mean to you to see your friend, your fellow digital creator, and also another Black woman, in this category?

I love Quinta so much. She’s one of those people where you knew it was a matter of time. She’s just so naturally funny, talented, knows what she wants, and is also so straight-forward. I think she’s a Sagittarius, because she just gives it to you straight. When she’s bothered, she wants you to know that she’s bothered; and when she’s having a good time, she’s just having a good time.

There’s just no one more deserving, and her show is so good. She’s just the perfect storyteller, and the perfect actress, and to see her grow into who she is now is so fulfilling. We have similar backgrounds, so it’s also funny, like, here we are meeting in the same category. I’m just so, so happy for her. And she’s making history along with her first Emmy nomination.

Rap Sh!t” is a family affair, because your sister [Elize Diop] is one of the writers.

To see her name in the credits was super, super special. This is her first TV show, and when I was writing this show, I knew that I wanted to have her be a part of it in some way, because I just knew that she could write for these characters and that she had such a sensibility for this show. I was so happy that Syreeta was willing to hire her.

What was it about her perspective on these characters that made you say, “She’s got this”?

My sister actually reminds me of Syreeta, they have a similar sense of humor. [Elize is] sharp, she’s witty, she’s also pop culturally in the know, like from the grittiest, gutteriest gossip, to being a mom and having that perspective. Between all of that, and just being a good writer, I was excited to try her out this season, and she beyond delivered.

You’d had the idea for “Rap Sh!t” for a while — and at one point thought about diving into the rap game with Issa Dee in “Insecure.” What made you decide to put pen to paper?

I was always thinking about it but wasn’t really writing [because] I was so busy with “Insecure,” and then a [music] producer, who shall remain nameless, made a comment about how most female rappers, all they rap about it is their pussies. At the time, it pissed me off, because I was like, “This is unfair,” and I used that as motivation to write the pilot and to put pen to paper. That kind of served as the foundation. Then I just thought about the other elements of what it means to be a female rapper right now, what it means to be an artist in this moment, and I just wanted to make a piece that reflected where we are culturally.

“Insecure,” starring Natasha Rothwell, Yvonne Orji, Issa Rae, Amanda Seales and Wade Allain-Marcus, wrapped up its final season in December 2021. Courtesy of HBO

Looking back on “Insecure,” let’s talk about the Season 5 premiere. What scene stands out in your memory?

The mirror moments — college “Mirror Issa” really makes me think about where I started the show, and a lot of the improv that happened like, on both sides. And then even my relationship with Melina [Matsoukas, executive producer], who lets me play a lot and who’s very, very transparent about what she likes and what she doesn’t like, her laugh is very distinct, so you know when you’ve gotten her and gotten something good. I also think about the scene with Lawrence (Jay Ellis) and ending it with him, where Issa essentially chooses herself and chooses her happiness, at that point in time, even though it hurts.

Tell me about playing the college version of Issa and getting to throw the braces back on.

That was me in college. I remember I got to see the first episode with my friends, and they were like, “Dang, you really nailed that! Like, that is how you looked.” It was just interesting to make fun of myself in that way, when, you know, I might have thought I was killing it back then.

“Rap Sh!t” is your second comedy on HBO Max, and fourth show. Did you ever have a point when you wondered, “Will anybody watch it?”

Of course, I think that all the time. I don’t know that I’ll ever get past that. And that’s also what keeps me going, those nervous butterflies of, “Are they gonna fuck with this? [Or] are they gonna be like, fuck it?” But I love creating so much, and that won’t stop me. If people don’t fuck with this one, I’m like, “Well, I know they’re gonna mess with this one.” It just gives me a lot more opportunities to continue to create and to top myself and my own expectations.

You’ve been so busy, have you had time to absorb these successes leading into the next chapter of your career?

I have, absolutely. This year, I’ve been having so much fun, and I have had moments where I’ve been able to really appreciate where I started and where I am now, to take stock of the people I love and taking in experiences. I truly feel blessed and grateful. This has been so much fun.