Insecure Creator/EP Issa Rae Talks Creating Content, the Sound of the Show, Season 2 and More 

Who doesn’t love a themed party to celebrate the digital download release of a great show? TV Goodness attended the #InsecureDownload party at The Den on Sunset earlier this week. Not only did I tie on one — I tried the Bish, Please! (so good) — but I also had the opportunity to listen to music from the show, meet other fans of Insecure and participate in a roundtable discussion with creator/EP Issa Rae.

Coming up [in the business], at any point did you feel like you had to water down your personality or who you are as a creator for people to understand your vision or understand how you want to tell your story?

Issa Rae: “Before this show I did. I was developing elsewhere and was just really super eager to please and felt like I had to fit within their mold as opposed to thinking they hired me for a reason. They want to work with me for a reason.

In hindsight, it was such a stupid thing to do. I was just like, ‘This is my one shot so I have to make sure it’s right and I have to make sure they like me and I have to make sure that it works within this mold.’ Ultimately when they passed on the project, I was devastated.

When the HBO opportunity came along, I thought, ‘I’m never gonna do this again.’ I have to recognize what I bring to the table and the story that I’m trying to tell regardless of whether or not they like it, is mine to tell. So that was a big learning lesson for me.”

There’s been so much talk about diversity. Why is Issa’s story important right now?

Rae: “I think it’s just because it shows a regular black girl experience. You don’t really get to see us in an unremarkable way. There are things that are very much unremarkable, but very much relatable. That, for me, is what makes the show stand out. I feel like people can watch and be like, ‘I know that girl. I am that girl. I made that stupid decision.’ Since the ‘90s we really haven’t had that.”

Just as important as your storylines, is the music. What was it like working with Raphael Siddiq?

Rae: “Raphael Siddiq is an amazing composer. I’ve always been a fan of his music and he’s just so gracious. He was always there early and ready to work and friendly and open. It felt stupid to give him notes just because he’s a musical genius and for me, I didn’t have the right vocabulary.

He was like, ‘What are you looking for?’, [and I was like,] ‘You know, just something hot.’ [Laughs.] ‘Like buck.’ He’s like, ‘Cool, cool, cool. Can you give me artist’s names? Artists that you like?’ So I gave him a list. He was able to perfectly give me the sound that I wanted for the show.”

There were a lot of times where the vocals really helped the storyline along. 

Rae: “Yeah. That was our music supervisor and consultant Kier [Lehman] and Solange [Knowles]. We worked with them just to choose specific tracks and to tell the story that we wanted to tell. Music was incredibly important to me in telling the story.”

I’m a big fan of your rapping. In Season 2, if you could get any rapper to come rap with you in character, who would it be?

Rae: “I think it’s Drake, hands down. [Laughs.] He’s appropriate. I don’t want to stunt cast with anybody, but we set him up so that’s only fair and right. We haven’t had any Drake love yet, but maybe. Maybe.”

I love the relationships, especially between you and Molly, and all the women on the show. Can you talk a little bit about that and making sure they were all different but supportive in really interesting ways?

Rae: “It happens in real life people I know. Even in the writer’s room, we constantly have conversations, we constantly tell stories about our friends and it makes it easier to tap into who real people are so, literally, if you’re watching the show most of what you see is from either my life or another writer’s life. Everybody has a piece or chunk or morsel of their stories in this show. We did that intentionally to create a very human story.”

Was there anything in Season 1 where the audience reaction really surprised you?

Rae: “Yeah, the finale. [Laughs.] To cause that much conversation and to be such a battle of the sexes. I never saw that coming. I wasn’t really thinking about guys in writing this show and creating this show. It’s very much my love letter to the black women in my life and to friends in general, so the fact that so many guys tuned into the show and reacted so strongly was crazy to me, but very much welcome.”

Out of all the episodes is there a scene or moment that’s powerful and meaningful to you when you watched it back?

Rae: “I love watching Jay [Ellis] in the fight scene in Episode 7. Watching him, he broke my heart every single time. He broke my heart in person and then I was still sad in watching him. I just think, in addition to Yvonne [Orji], they’re phenomenal. I feel so blessed to work with them. It’s like sparring. They make me better.”

What would you say is the biggest lesson for Issa the character after 8 episodes?

Rae: “What was the biggest learning lesson? I think she did a lot of lying to herself, so I think it’s figuring out why she did that and what that means for her as her journey continues ‘cause she definitely saw the consequences.”

And for you as the creator of the series. Did you learn anything?

Rae: “That I shouldn’t have named the character Issa.” [Laughs.]

Will it help you, as a creator, to tell the story across ten episodes for Season 2 versus the 8 that you had for Season 1?

Rae: “That’s a good question. We’ll find out. You’ll let me know. People will let me know.”

Are you allowed to tell us anything about Season 2?

Rae: “Only that we’re picking up where the story left off.  We’re still continuing to tap into real life. We like dealing in the gray area.

A lot of the stories we like to tell, we don’t want to make a big statement because I don’t feel like life is a statement. So many things happen and most of us are trying to figure out what to make of that and how you attribute that to how you grow and evolve as a person. This is a very specific journey-driven show. Know that we’re telling a very finite story.”

When you were starting out what was your biggest dream? Did you ever think you’d have a show on HBO?

Rae: “I said that I wanted a show on HBO or FX. I said that early on and forgot I said it until someone reminded me. They were like, ‘Oh you said it in this interview.’

Speaking things into existence is a real thing and when I got that opportunity, I remember getting that call. ‘HBO wants to meet with you. They want to know if you have anything that you want to pitch,’ and I called my friends and was like, ‘This is so great. HBO called.’ [Laughs.]”

Now that you’ve gone on to do the dream of every YouTuber, which is to come off the platform and create your own content, how does that weave into the space of how you want to tell stories going forward?

Rae: “My YouTube channel is still active. I’m still working with other content creators. I currently have a situation. I’m involved with HBO [Laughs], so it’s a matter of balancing that because they’ve given me an opportunity to work with other creators on that platform — GO and HBO proper, but I love the digital space.

I love YouTube specifically because it’s where you get the most raw, pure voices and I don’t think I’ll ever stop making content online.”

Going from that space where it’s constant commentary on everything you do as soon as you put it out, did you find it a better fit or process to be able to create without opinion?

Rae: “Yes and no. I guess overall, yes. I’m so impatient. Sitting on those episodes and having them done in the can and watching week to week, people be like, ‘Ok. I guess I’ll fuck with this.’ [Laughs.] ‘It’s cool.’ And I was like, ‘You don’t even know what’s coming! Just release all the episodes now.’

I was very impatient. It was a struggle. I was saying early on, I think the biggest pressure in Season 2 is just knowing people have seen the show and there will be new expectations. You can’t help but consider what people have said about the show. So it’s very much like trying to ignore what people are saying and focus on the specific story we’ve been trying to tell and not trying to please the audience in any way.

That was the beauty of Season 1. We didn’t have an audience; we were just creating. So, for me, it’s just making sure to stay true to the characters and the story we’re trying to tell.”

What challenges did you have having your content live on digital and crossing over to HBO, specifically with Awkward Black Girl and now Insecure on HBO?

Rae: “I guess it was just feeling impatient. Just knowing that I could have an idea and have instant feedback. ‘Oh, people hated that. Cool. Let me just do the next one.’

I wasn’t used to doing 7 or 8 drafts of something and that’s a great and a bad thing because I could get in my head or I could produce something that wasn’t necessarily the best. With this, getting adjusted to multiple drafts of something, I don’t necessarily know whether or not this is gonna be put out there.

Their hands, at the end of the day, say yes or no. I could lose this forever no matter how passionately I feel about it, no matter how much I feel like I’m telling a good story or a story that people respond to at the very least. So having that in their hands was challenging, but once they say yes it was just no looking back. I was ready to go and the team we assembled made it that much better.”

How did you assemble a team that could help execute your vision?

Rae: “I love passionate people. I love people who are just as driven as I am. In our own small company we just have amazing team members and PR and on the production side, on the business side. They’re all people who are all the same age, pretty much, or younger. The common link is that we’re always ready to go, we’re always ready to work. I love that aspect, that passion. I wanted the same when Insecure got picked up.

Our showrunner was young, hungry. He came up in the writer’s room world. He was egoless and he was down to tell a good story. He was constantly checking in to make sure like, ‘Is this what you want to do? Does this still feel like this is your vision?’ At the same time, secure enough in himself to challenge me and be like, ‘What do you think about it this way? Do you think it could be better if we do this?’

I love that dynamic and even in finding Melina [Matsoukas]. She was looking for a television project or a film project that she was passionate about. She took this and ran with it. She had a lot of experience in the music video world [and] was able to humble herself and be like, ‘I don’t know that much about TV, but I’m still gonna be confident enough in what I can bring to the tablet to make this show.’

Just to be able to speak the same language with them, involving people of color and black people. There was an added benefit there too. So, passion and drive and humility are things that I appreciate.”

What was your biggest fear in transitioning from Youtube to mainstream?

Rae: “My biggest fear? Just losing people that I love to work with daily. For some reason when you start out small, it gets hard. Now we’re taking on a lot more and I want to make sure that everybody can come along, but I have to be realistic and realize sometimes that’s not gonna be the case.

I don’t like to think about stuff like that. I genuinely love everyone I work with and hope that we can move forward together.”

Edited for space and content.

Get your digital download of Insecure here.