Q&A: Issa Rae on HBO, the Struggle to Create Awkward Black Girl and the Current Political Climate

'This show lived because of the Obama administration'

Photography by Chris Loupos for Adweek; Styling: Jason Rembert; Hair: Felicia Leatherwood; Makeup: Joanna Simkin

Issa Rae, the creator, star and executive producer of HBO’s Insecure, graced the cover of Adweek’s Young Influentials issue this week and spoke about her career trajectory and what she’d like to conquer next. (Spoiler alert: She wants to have her own empire.) But Rae covered so much more in our interview—discussing HBO’s commitment to the show, transitioning from creating on her own dime to working with a network, sex scenes, the current political climate and more. Here are some of the most interesting moments from our interview that didn’t make it into the feature:

Adweek: For Season 2, has HBO been more invested? Given you a bigger budget? More time?
Issa Rae: They recognized a lot of what held us back the first season and said, “Hey, we definitely understand the type of show you are this time around, so we want to give you an extra day of shooting.” Whereas last season we only had five days to shoot one episode, this season, we had six days to shoot an episode which is a huge difference.

Also, we’re a very location-heavy show, so they made sure the budget reflected that. The Staples Center was super expensive to shoot in, and it was going to be outside of our budget. We were coming up with alternatives with our producer to figure it out, and Amy (Amy Gravitt, our EP) was like, “If Silicon Valley can shoot at Staples, then Insecure should be able to shoot at the Staples Center. We’ll put the extra money towards it.” They’ve been really supportive. And then, of course, in putting us behind Game of Thrones—they’ve shown us that they believe in the show.

What’s the experience been like shifting from having no budget and doing your YouTube show to having HBO behind you?
A relief to be honest. I feel so lucky to be able to experience and to work with people I like and respect and I’m learning from constantly. The internet show felt fun for a while, but it was such a struggle. We would finish them minutes before and upload them. There were rarely times where we were ahead of the game. And it was just so many hats at the same time. There’s a novelty to that where it’s like, “Oh, the struggle is what made it appealing, but after a while, it gets exhausting. People have real jobs and then careers, and nobody can live off of this [internet show]. So [it’s a relief] to be working with people that are paid properly, so that part’s taken care of. So there’s no resentment or concern. You can just focus on being creative. It just makes everything more fun.

A lot of people don’t realize how much work goes into trying to create something on your own.
Not at all. It would be reflected in the comments if we uploaded an episode late. Actually, the finale for Season 1 of Awkward Black Girl was a day late, and we stayed up all night. We tried to—people threw watch parties to watch the finale, and they showed up at bars. They were livid that we didn’t get it up on time, and they acted like it was a choice. But we were trying. That would never happen now. HBO would be like the season finale airs tonight. Unless like a catastrophe happened, you know you’re guaranteed programming.

Do you actually have the creative control that you want at HBO?
I mean, all of it. It’s a very collaborative process. Obviously, [Insecure showrunner Prentice Penny] and I need to be on the same page, so we always take what we come up with in the writers’ room, shape it, and then I end up being the final force in terms of making sure that it’s through my lens and then all the verbiage. Then once we get it to HBO, it’s great because there are two executives that we deal with. And then [HBO president Casey Bloys] will weigh in, and Casey started out as a development executive. But he’s the one who brought me in.

It feels really intimate, and they trust us, especially with cultural things. Where they’re great and where they excel is story notes. In the past two seasons, they’ve uprooted our entire timeline. I remember the first season—we were all shaken to the core because we were halfway through, we knew what our finale was going to be, and they were like, “Move it all up because it feels like things are taking too long.” I was like, “But we just lost three episodes.” It ended up being the best thing ever. It forced us to just come up with new and innovative ideas. Eight episodes—that’s not a lot. So you really do need to trim the fat. It happened again this year.

You just landed your first big film deal with George Tillman Jr.’s adaptation of the best-selling YA novel The Hate U Give. When will you do that?
I start in a couple of weeks, actually. I’m really excited about it because I love the book and George Tillman. I sat down with him, and being able to hear his take on what he wants to do with the film, and I’m excited about the cast. It feels so timely and I’m just happy to be a part of it and to do something different than TV.

Can you tell us about any other projects you’re working on?
I can’t say. They’re movies that I’m writing, but I can’t specify just yet which ones they are.

There was some chatter about the lack of condom use in the sex scenes of Insecure. You tweeted in response to fans questioning that. Did you feel compelled to respond?
Yes, I did, because one—we’re very engaged with the audience. I’m a real live Twitter social media user so it’s not like I can—there are things that I ignore because I’m like, “Oh, it’s none of your business or I don’t feel like talking about it.” But for this particular issue, people were concerned and initially I was like, “What the fuck? What is going on?” But then realized [after] reading the reactions that it’s a compliment because people feel so invested in these characters that they see themselves in these characters. Their minds are like, “If I was going to do a ho phase, I would wear a condom.” And two—just as a storyteller, if that was taking people out of the story, then I just felt compelled to address it. I don’t want you—given all the work that we put into creating a scene, the dialogue, everything—to take you out of it and you’re like, “Where are the condoms?” And you miss something that we said. It just felt important. It’s not a big deal to address it and knowing that there are more sex scenes to come, I don’t want the conversation to continue without saying something. Yes, we’ll do better. That’s all we can do.

There is a storyline this past season where Issa’s white co-worker is uncomfortable with the way that Issa handles the school principal excluding Latino kids from We Got Y’all. Can you tell us a little bit of where that came from and what you wanted to show there?
I knew that even in conversations with Prentice that I wanted to touch on the black and Latino dynamic in Los Angeles.  When I moved back to L.A. as a child and then later growing up through the school system, there’s just a clear tension. And it’s never really addressed in a casual way. 

Given Frieda’s bleeding liberal heart, her witnessing that dynamic and struggling with that was something that felt compelling and interesting. It also happened to fall in line with a lot of the anti-Mexican rhetoric that our No. 45 [President Trump] has been battling. So it just felt timely in that sense to address how we kind of all play a part in it. That’s kind of where the germ came from and just feeling like we wanted to address it in a very gray area where we’re not, where Issa is complicit, but you also see why she’s doing what she’s doing. [It also gave] Frieda a leg to stand on. 

The reactions have been interesting because … I saw someone write [that] Frieda is the white woman who wants you to do something about racism as opposed to doing something herself. I think her way is getting Issa to do something about it. It’s just like, “Why don’t you speak up?” In her mind, she’s like, “It would mean more coming from you, and I don’t know the best way to do it.” Even starting that conversation has been really interesting to witness. It’s also been interesting to witness people who gloss over it all who are just like, “[Issa’s] going to do what she has to do. What is she supposed to do?” So I love that you kind of get a lens into people’s personalities just by their reactions to certain parts of the show.

What was it like to work with Larry Wilmore?
Larry is great. We only got to work together on the pilot, and then he had to leave. Then I had to redo the pilot, but he was always super, super encouraging. He’s honestly who helped to build my confidence in terms of navigating notes. As common sense as that seems, it just wasn’t something that crossed my mind. I felt like I just had to make [all of the notes] work. We’re working together now on writing a movie together. We just got off the phone this morning for notes. He’s a great idea man. 

As a prominent young creator, does the current political climate that we’re in … influence the way that you’re creating stuff or the projects that you’re interested in?
I think it’s definitely made me a bit more on my heels and conscious about even certain jokes that I’m putting out there. You know, my dad is Muslim. We had a Muslim joke in the first episode and [director Melina Matsoukas] after seeing it was like, “This is kind of offensive just given the climate.” I didn’t think anything of it at the time and then realized like, “Oh, my gosh. I don’t want to perpetuate anything this man is touting.” Given my affiliation with Islam or not … I just don’t want to bring [that out]. So in that sense, it’s made me think about the images and even the specific mindset that I’m projecting. 

But I also am aware that there are certain things that need to be seen, and it just makes me take more pride in the work that we’re doing and the importance of the things that we’re talking about. I don’t take that lightly … but I don’t want this to be a show born out of Trump rebellion. I want it to be an Obama show. This show lived because of the Obama administration and the confidence that instilled in young black people everywhere. I very much feel like that.