Insecure’s Issa Rae on her character’s growth and bringing the show back to its roots

This may not be Insecure’s first year in the Emmys spotlight, but 2020 is easily its biggest. With eight nominations total, an overdue Outstanding Comedy Series nod could not have come at a better time: As we noted in July, season four of the Issa Rae starrer rendered some of the most engaging television we’ve watched thus far, thanks, in large part, to a long-gestating friend break-up between Molly (Yvonne Orji) and Rae’s namesake character. Busting up the central friendship might not be ideal for other shows, but for the HBO comedic tentpole, the move culminated in rounds of deeper character exploration and emotionally arresting performances from the entire cast, especially when it comes to Rae and Orji.

With many of the show’s key relationships up in the air, it’s hard to predict the direction of season five (and fruitless, as the pandemic has paused production in the early stages, so the team is still determining many of the details). Wherever it may be heading, Issa Rae is particularly excited to explore her fictional counterpart’s continued growth. The star and executive producer talked to The A.V. Club about production of webseries Awkward Black Girl, the weight behind saying that you don’t “fuck with” someone anymore, and bringing Insecure back to its roots.

Issa Rae: I was on a Zoom call, in a team meeting. One of my producers, [Deniese Davis] read that I had been nominated and I was like, “Oh, that’s dope!” We continued the meeting and then she said, “Oh, and Insecure got nominated,” and I got excited, but we still continued the meeting. And then she was like, “Oh, [co-star Yvonne Orji] got one, too.” And that’s when I got super excited and was like, “Okay, I got to go.” [Laughs] It’s amazing.

AVC: It was really satisfying to see the major acting nods this year because this was such a meaty and emotional season. What is something that people didn’t tell you about getting an Emmy nomination?

IR: I know a lot of us feel almost robbed in a way. We don’t get to go out and celebrate together. The writers’ room celebrated on Zoom and got a little too tipsy. Now I’m just walking around with the air of excitement, and it lasts a really long time with the coverage and the amount of flowers. That’s something that I didn’t know would be such a big deal. I had flowers for days and I’m terrible at taking care of them, so two days later there were dead flowers in my house. But I was truly honored. It’s just really considerate. And there’s lots of champagne, which is really where my heart is.

AVC: It’s been nine years since the premiere of your web series, Awkward Black Girl. Are there any creative processes or habits from that time that you still use to this day? And is there anything about that process that you had to give up once you transitioned to HBO?

IR: I definitely take the aspect of collaboration from it. There’s still a constructive feedback element that I’ll always value in my work. Even with Awkward Black Girl, halfway through the season we [secured] a meeting room, me and three other writers. So there are elements that I took from there and then perfected it at Insecure with the help of [showrunner Prentice Penny].

I strongly believe in good character work. There’s still something I like about caricature-like characters that feel grounded—or archetypes—and I think that reflects in a lot of my work, in general. I just believe there’s a commonality and a relatability of seeing people that everybody interacts with, like, “I know exactly what this type of person this is,” “I’ve been around or identify with this person,” or “This is the type of person that gets on my nerves.” That’s always gonna be present in anything I do, and that’s something that I definitely brought from Awkward Black Girl.

Workflow-wise, it’s changed so much for the better because Awkward Black Girl was so rushed. Week one, we were always writing, week two was shooting, week three we’d edit, and week four we were putting it out. Then the cycle would happen all over again. Obviously now we have a little more time to breathe.

AVC: Season four was obviously an intense time for Issa and Molly, but it was also a really prosperous time for Issa as an individual. She founded her niche in community organizing, had these really lovely familial moments with her brother and her mom, and explored herself while she and Molly were on pause. As a creator, which moment of growth was the most satisfying to witness?

IR: Putting that block party together. It’s just something and I can identify in my own personal life—having an idea and then overcoming the doubt, naysayers and obstacles in order to bring something to fruition. It was just such a satisfying feeling to watch Issa do that over the course of two seasons after having quit her job and being in this low uncertain place. That felt really satisfying. That’s one of the things that I wish we had captured a bit more of, watching her taking in the block party a bit more. That’s a big accomplishment for her, which was obviously diminished by the big fight at the end. But before then, while walking on set it was like, “Look at what Issa did! Issa didn’t do this shit.” It was a running joke. It was like, “Damn, even our own writers can’t believe that Issa did all this.” But I’m proud of her.

AVC: As for Issa and Molly, it was the toughest friendship breakup to witness, because it felt real. We’ve obviously seen Molly and Issa have spats leading up to this and they’ve always kind of resolved it quickly. Was a breakup of this magnitude something that was in the works from the beginning, or was it something that unfolded naturally during season four planning?

IR: It was actually something that unfolded during the end of season three planning. This is no disrespect to Girls; this is just about like their form of story telling. But the girls and Girls outgrew each other—they were fighting all the time and they didn’t feel like genuine friends. Since [Issa and Molly] are the core friendship of the show, Prentice and I were just like, “We have no interest in telling a story about frenemies.” But the decisions that were made in season three really led us to this rift in season four. And that was something that really excited us, especially by the end of the season three finale, Molly had made this choice for Issa and they sort of saw each other with new eyes. [Note: At the end of season three, Molly sent Nathan (Kendrick Sampson) away from Issa’s home when he returned from a lengthy mental health break.—Ed.] So that was really exciting territory for us this season.

I remember at our annual pre-room meeting, Prentice and I usually will bring to the table we’ve been thinking about for the season and just do a kind of idea vomit. He was thinking about coming into this season with Issa just saying, “I don’t fuck with Molly no more,” or “me and Molly don’t talk anymore.” And we immediately took to it, it sparked so much.

AVC: That’s a heavy saying, “I don’t fuck with that person anymore.” You can say you’re not talking to someone or that you’re not seeing eye-to-eye with a person, but “I don’t fuck with her anymore” is like friendship divorce.

IR: Yeah, you’re condemning them to nothingness, to no parts of your life at all. And Issa wasn’t even fully [fighting with Molly] yet; she was still being dramatic. So I can only imagine what she would have said post-block party.

AVC: We talked to Jay Ellis prior to the season premiere and we asked him what he thought ultimately binds Issa and Lawrence together. He gave this really lovely answer: “I think if these two people met at a bar tomorrow, they would spend the next five years together. Of course they have their moments, but I think they truly see and want the best for each other.” Do you agree or do you have a different philosophy?

IR: I agree that they want the best for each other, but that doesn’t mean that they’re the best for each other. I think that’s the big question between them.

AVC: “Lowkey Happy” was such a nice bit of romantic television that showed how Issa and Lawrence had naturally grown into each other in a mature way. And then the finale happens and there’s this huge bombshell of a reveal where we learn that Condola is pregnant with Lawrence’s baby, just as he and Issa were figuring things out. What was the conversation like surrounding that moment?

IR: We had so many conversations around what we wanted to bring the show back to. The show is, at the end of the day, about Issa and Molly. We had fractured this very important friendship. In addition to this dramatic event of searching for [Amanda Seales’ Tiffany] and reminding them how important it was to be there for each other and vigilant about what was happening in each other’s lives, we also thought about everything that had built up between them. Molly told Issa, “Your life doesn’t have to be this messy,” and there was a bit of truth to that. Issa told Molly at the end of episode two, “Sometimes it feels like you like drama,” and in episode five, “If things don’t work out with Andrew is not going to be because of me.” So they were seeing the worst in each other, but we also like the idea of them kind of being right about each other. So the question was, how are you going to help one another grow out of that? And how are you going to grow to be better with each other?

Also, seeing Lawrence’s character level up in a way, there was something interesting for us about seeing how he would handle these cards that were dealt to him in a way that intrigued us. And then there are other reasons as well that will reveal themselves next season.

AVC: Do you have a favorite line from season four?

IR: There was an episode where Issa and Kelli (Natasha Rothwell) go back and forth when Kelli says, “So you fucked Andrew,” and Issa says, “Not even close.” Kelli responds, “But I’m in the ballpark, right,” and Issa was like, “You’re not even in the game.” It went on even longer than that with Prentice coming back after each take and adding a line.

Anything Natasha says, I break. In episode one, one of my favorite lines of hers didn’t make it because I laughed over it. Issa asked, “Hey, have you ever had a girl that you became friends with start to get at your ex?” And Kelli’s like, “Oh yeah, that happened to me. But I framed her. She’s in jail now. We’re pen pals.” So I improvised, “Oh, you’re [penitentiary] pen pals?” And Natasha responded, “Oh, that’s my GIRL!” Her enthusiasm caught me off-guard. Now I say it all the time, and it didn’t even make it to air.

AVC: That’s a shame. There’s always this hope that Issa and Kelli will one day get a bottle episode.

IR: We try every season to give Kelli a bottle episode, but then we’re always like, “Okay, we’ve got to get back to the story.” We have to figure it out. We’re working on it.

AVC: Are there any hints about season five’s fake show within a show?

IR: Those usually come about in the writers’ room. The last one came about because we were all listening to true crime podcasts. Since we’re not in a room this time, we’ll have to see where the inspiration comes from. There were a couple of ideas that we previously through out there that were excited about, but we’ll see.

AVC: Lastly, in what way do you hope to see Issa continue to grow in season five?

IR: In so many ways! With her reunion with Molly at the end of season four, it’ll be exciting to see whether they’re going to grow together or decide that they are better apart. I’m excited that she’s found her career path—a passion, even—which is a long way from where she was season one. We’re frequently referencing season one career-wise for season five, just in terms of showcasing her work journey. She’s come a long way.