Issa Rae Once Congratulated an Actress Who Lost an Emmy for Winning
In the two years since Insecure premiered on HBO, creator and star Issa Rae has transformed herself from an Awkward Black Girl into a veritable mogul. When we sit down in her hotel room to discuss the new season of Insecure, Rae has just finished shooting Little, a movie she describes as “the reverse Big” conceptualized by then-10-year-old Black-ish star Marsai Martin. Now, she can finally tackle her never-ending list of projects in development, including another HBO show, Him or Her, which she’s creating with former The Daily Show writer Travon Free. In October, she’ll appear in the adaptation of Angie Thomas’s wildly popular YA novel, The Hate U Give. Oh, and then there’s the next season of Insecure, which Rae is already thinking about, even though she’s got a million other things to do.
“Anything that’s not moving forward right now is literally because of me,” she says. “And I’m so happy. I just finished shooting this movie yesterday, and I can finally dig into all the projects that are pending.”
But first, Insecure Season 3, which Rae describes as a period of “starting over again” for the show. “One of the things me and Prentice [Penny, Insecure‘s showrunner] talked about is, we never want you to feel like you know the characters and you know what the show is,” she says. Season 2 “closed so many doors,” she points out, and Issa Dee is ready to start anew—that is, after she gets her financial situation in order, and moves out of her “not-really ex” boyfriend Daniel’s (Y’lan Noel) apartment.
Despite her in-control, top-of-the-world presence, Rae insists she’ll always retain her fictional alter-ego’s awkwardness. Following our interview, she sat down for a rousing game of Never Have I Ever over shots of champagne and opened up about her most starstruck moment—it involved Rihanna, of course—and that time she congratulated an Emmy-losing actress for winning. Watch above, then read on for a preview of Insecure Season 3—and the truth about Lawrence.
HB: Let’s start with the premiere. I was not expecting Issa to be a Lyft driver. Where did that come from?
IR: It came from me actually trying to become a Lyft driver last year. When I was writing the first episode last season, I went to Malibu to get away, and I rented a car, and you have to buy a full tank of gas. Well, I bought a full tank of gas. So by the time I finished in Malibu, I hadn’t used it all, so I was like, I’m not gonna return this car and I paid for this gas. I’m not returning it with a full tank so I lose my money. So I was like, let me sign up for Lyft. I can get rid of the gas, have great adventures. And I signed up and got my stickers and stuff, and then I got rejected. I got an email that said because I had a violation in 2014, I was ineligible. It curbed my adventure.
So I told that to the writer’s room, and they thought that was completely absurd that I wanted to do that. They were like, you should’ve just returned the car. And I did return the car and they refunded me the money, so I didn’t even need to do all that. But I still was like, I would totally do that. If I weren’t doing what I was doing now, I said I would be a waitress. And now I can add Lyft driver. There’s so much! You get to know people, and it feels like even in Issa’s current state, it’s a great way—especially in L.A., there are a lot of creatives who need a side gig—it’s such a flexible career that it seemed natural for Issa in her need for extra money to take this profession on.
“If I weren’t doing what I was doing now, I said I would be a waitress. And now I can add Lyft driver.”
HB: Issa got approved even with her car accident?
IR: [Laughs] You’re asking all the right questions! We don’t know who was at fault. Lyft doesn’t know.
HB: Let’s talk about Issa’s headspace this season. She feels like she’s in a better place following the finale, but you’re never quite sure with her.
IR: I would say that that part of her life that plagued her, she got closure for that part. But everything else is still fucked up. You know, she’s living with her not-really ex, she’s broke, she doesn’t have an apartment. I wanna get her to a point where she’s just barely floating above water to swimming. She’s a little tired of just making it. [She’s like,] “I wanna swim, I wanna flourish.”
HB: There’s been a lot of chatter about no Lawrence this season. Can you speak to that?
IR: In talking about where we wanted the characters to go, by the time we got to Lawrence, I was like, “They had a great conversation. Should he be here right now?” And the decision was no. She was moving in with Daniel, so it felt exciting to be able to go into his perspective. We didn’t expect the male response for the show to be so positive. People related to the Lawrence character so much, but the idea of telling a different male’s [perspective]—Lawrence and Daniel are so different, the idea of getting a sense of who [Daniel] is, because we’ve only seen him through Issa’s eyes, her dreamy what-if eyes—it really excited us to be able to paint him as a whole, 3-D person.
HB: How do you walk the line of, we have this fan-favorite character, but also we have to serve the story? Is there a struggle there?
IR: No, I never wanna serve the fans. I never wanna serve the Internet, Twitter, whatever. I just wanna tap into real life. In real life, when exes have left, you know, I barely see them. I strongly believe that so many of them pop up when you’re doing great, but for the most part, I don’t keep in touch with exes when I’m in a relationship, or even in general. I like to move forward not backwards, so we wanted the work to reflect that.
HB: What is the writing process like for you? Are you jotting notes down in your car at red lights?
IR: Yes! I just did that. I did that, I woke up out of my sleep to write a note down. I don’t even wanna think about Season 4, but I’m “thinking” about it. And you never wanna forget exploring things. I use my little Evernote app and constantly have a running page.
HB: Do you ever write something and then you get to set that day and you’re like, “What?”
IR: [Laughs] Or I write it and I’m like, what the fuck is this? What did I mean? “Chicken wing”? It happens all the time, and you just do what you do.
HB: What was the most fun storyline or even scene for you to tackle this season?
IR: It comes in Episode 5. The entire episode was very fun to shoot, and we tease it at the end [of Episode 4]. I think the fifth episode is really fun and special, so much so that we’re getting in trouble for it. But we’ll see when we get there.
HB: For a character so loosely based on you, what’s the most difficult part of being associated with her face, her name, her actions…?
IR: Everything. People already can’t distinguish real life from characters, so I don’t make it easier by having the same name as the character. I think just going into the street, the most annoying question that everyone thinks they’re original asking is, “Where’s Lawrence?”, “Where’s Molly?”, “Oh, you cheated.” You know, “cheater.” When Issa cheated in Season 1, I could not go anywhere without being called a cheater. Or people telling me that they were Team Lawrence. But, at the end of the day, it’s flattering. It’s a small inconvenience for people liking your show.
HB: What is the hardest part for you going to set and getting into character as Issa Dee versus being Issa Rae, the creator, the executive producer, the boss?
IR: It’s always fun getting into character, especially when I’m in scenes with Yvonne [Orji] or Jay [Ellis] or the girls. It’s more thinking about the other things. If we’re going too long on a day, I’m like, is this gonna be on budget? What is this gonna cost us down the line? It’s really separating that because sometimes I might have to be happy and jovial in a scene, and in the back of my mind I’m thinking we’re gonna be over budget and we’re gonna have to shoot on a Sunday. So that’s hard.
HB: I saw your tweet about Jezebel’s Erika Alexander piece, where you wrote, “So appreciative of those who made me think I could and who continue to inspire me.” I thought that was so touching, and reminded me of a lot of conversations I’ve had around imposter syndrome, about how you find the courage, or give yourself the permission, to be yourself. So many brilliant, creative women second-guess their own abilities. I’m not sure if anyone overcomes it, but how did you realize you had a right to use your voice? How do you shut off the voices in your head going, “this is not a good idea” or “this isn’t gonna work”?
IR: I guess I’m over those voices because I would feel worse if I didn’t try. I would feel so much worse if, like with Awkward Black Girl, I had been like, “I don’t have the resources, I don’t have the money,” and then I saw that someone else did it. I would not be able to live with myself. Because I’ve seen that happen before. And so that fear of someone else doing it before me, and me never realizing my dreams or me not even being able to try, that cripples me, or drives me to action more than, “What if they don’t like it?” Or “What if it’s not good?” I just don’t like living in that.
“That fear of someone else doing it before me, and me never realizing my dreams or me not even being able to try, that cripples me, or drives me to action.”
HB: On a non-Insecure note, we’re all so excited about The Hate U Give. What can you say about it?
IR: I haven’t seen it yet, but it’s gonna premiere at the Toronto [International] Film Festival, and that’ll be my first time seeing it. But I’ve heard great things. I loved the book. I think Angie Thomas is incredible and I can’t wait for her second book. But even just working with Amanda, she was stellar. She could get in her zone like that and really identify with the character, and it was such an honor to play April.
HB: How do you approach projects like that, ones you’re involved with in a behind-the-scenes capacity such as writing or producing?
IR: I just let myself be the visionary’s property, if anything. I love just taking a step back and being like, “Tell me what you do, tell me how you see it, and how can I help you translate your vision?” Because on something like Insecure, I’m involved in every step of the way and it’s so much of me. You have to answer all these questions, and you have to know all these answers. So I just love being a vessel.
HB: You came to stardom working on something that was your brain child, which is different for somebody who was an actor working with different directors and writers and producers through the years. Do you feel like—not that you missed something—but there might have been a learning curve in the other direction?
IR: I think being in the writers’ room was definitely a welcome culture shock because I didn’t know what to expect, and you have so many vets who have worked in other writers’ rooms who are accustomed to a certain way things go. But I’ve learned so much from being in that room. I’ve learned how to run my own room. And I think the “why” of it, like, “I was able to do this for cheap online, why can’t we do it this way?” And that [answer] is sometimes just, “Because people would die. You can’t just put a camera on the car because that’s not how it works.”
HB: Did you do that?
IR: We tried to. Nobody would listen to me. But on Awkward Black Girl, yes! It was like, “Friend, hold the camera and ride along with me in the other car.” So, you know, it’s bootleg ways, but I’m like, “Why is it taking us three hours to set up a process trailer when we just put Bob in the car and film us? Why can’t we do that?” But I don’t make the rules.
HB: What’s the hardest part about being associated with the term “awkward”?
IR: That people won’t see anything other than that, I guess. Which is fine. I’m like, that’s just who I am, and I’m not ashamed.
HB: How do you navigate those situations now, when you realize, “Oh, I can pull from this for my work?”
IR: Those embarrassing moments, those moments of discomfort—I don’t know what it is about them, but I really love depicting them because they do feel so excruciatingly relatable. I’m just like, why? Why did that affect me so much? Like, why do I care if someone saw me almost trip? Why do I care that someone thinks I don’t know their name? Why does that embarrass me so much? Why can’t I just go up to them and ask? “Sorry I forgot. What’s your name again?” Those things, what drives that, there’s something about that that’ll always affect me. We all have our things.
HB: Does anybody come back to you and say, I know you took that from that one time between us?
IR: One time in my Awkward Black Girl days, I specifically created a baby-voice character because of this one particular person. It was a girl, and I made the character a guy, so problem solved. But she texted me and was like, [adopts a squeaky voice] “Is this about me?” And I was like, “No, girl. You vain.” But I was so surprised that she knew it was about her because he played it completely different than her. But that was the one time.
Actually in Insecure one of my friends, her life mirrors Tiffany. And I did, I told her I mirrored her and her marriage. I made them the worst version. I made Derek and Tiffany the worst version of my friends, a couple. And she asked if it was about her, and I was like, “Yeah, but, you know, the worst versions. It’s not like, following your life.” And then I made them pregnant and then she happened to announce that she was pregnant, and she was like, “Now people are really gonna think this is about me. It’s enough.” But other people, like the main people who should know, don’t know.
HB: You mentioned that all the projects you have in development are held up because you’re busy. How do you decompress? What’s me-time for you?
IR: Me-time is getting away from everyone and everything, not responding to my phone, and really surrounding myself with friends and family. I haven’t had that yet, but it’s coming. I really have to be like, “No, I’m not doing this, this is blocked off.” I realized how important that is because people will keep throwing stuff at you. And there is a fear that nobody’s gonna ask me to do anything again, but I can’t let that drive me. The personal sanity is so much more important.
HB: Last question: what’s one piece of art you’re really loving right now—can be a book, movie, TV show, podcast, anything.
IR: I just started watching Atlanta again. I just saw the Teddy Perkins episode this past weekend. My brother showed it to me and I was just in love. It’s just so dope that [Donald Glover] gets to do this, and it’s good, and it feels relatable, and it’s art. And I know I’m late for Season 2. I saw it on a plane! But I’m a super fan. It’s so exciting to watch.
Insecure airs Sunday nights at 10:30 p.m. on HBO.
This interview has been edited and condensed for clarity.
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