Will white people like this?

It’s a question that Issa Rae has never asked herself. And thankfully, it shows. In her new HBO comedy, Insecure, Rae tells the story of two black female friends going through a quarter life crisis. There are no token white friends. No “gin-and-juice-smoke-weed-everyday-f*ck-bitches-get-money” kind of guys. And no stereotype that shows up onscreen without a wink and a nod.

“I just wanted to showcase the diversity of South Los Angeles… and demonstrate it in a real way that was authentic to me,” Rae told me before the premiere screening in Oakland.

The creator, writer, and star of Insecure has been creating and portraying compelling characters for over five years. In 2013, Rae was catapulted into Hollywood via her DIY web-series, The Misadventures of Awkward Black Girl, which led to a bestselling book by the same name and eventually – after three years of development – to eight episodes of Insecure.

If Awkward Black Girl served as storytelling boot-camp, Insecure is Issa Rae’s master class on how to write three-dimensional characters that are both funny and real. But don’t think of her HBO show as a reboot, or a sequel, or a spin-off.

Kimberly White, FilmMagic courtesy of HBO
Kimberly White, FilmMagic courtesy of HBO

Awkward Black Girl was the mixtape. Insecure is the album,” Rae said. The HBO show and the web-series may be two distinct works, but they’re definitely by the same artist. They share her signature.

Issa Rae sat down with me to talk about her creative process, the secret to creating authentic characters, and why Insecure is really just her love letter to Drake. Our interview has been condensed and edited for clarity.

Did HBO fly you out here on their private plane?

Issa Rae: I wish. I’m not there yet. The show hasn’t even premiered! I’m not getting the Sex and the City and Silicon Valley treatment yet. We got to get a second season.

The relationship between your character, Issa, and her best friend, Molly, is a highlight of the show. Did you set out to write a show about female friendship?

It evolved into that. Initially, Molly was a part of Issa’s life, but as we started to develop it more, we just loved Molly’s character so much and thought it would be great to show a two-parter. Script-wise, these characters had such great chemistry and informed each other’s lives. So, Molly just grew into a way bigger role. I’m happy with where it is now and getting to see what Yvonne Orji, the actress who plays Molly, brings to the character.

How important was it for the show to have a mostly all-black cast?

It wasn’t important as much as, this is my experience and this is what I know. I just wanted to showcase the diversity of South Los Angeles in that particular area [the show is set and shot in Inglewood] and demonstrate it in a real way that was authentic to me. [Having an all-black cast] came from a real place.

Courtesy of HBO
Courtesy of HBO

In Awkward Black Girl, your character had a white boyfriend. Are we going to see an interracial relationship in Insecure?

You will hear about interracial relationships throughout, but not for the main characters this season.

Solange Knowles is a music consultant on Insecure. Have you listened to her new album, A Seat at the Table?

I listen to it on repeat.

One of my favorite songs is “F.U.B.U.” which stands for “For Us, By Us.” Thinking about that concept in terms of Insecure, do you ever sit down and think: Are white people going to like it?

Hell, no. Never. The first question I ask is, do I like this? Next question is, are my family and friends going to laugh? And then, depending on the story, if it’s an authentically black story, I don’t care about anybody beyond that. But when white people do start watching, I love it.

With Awkward Black Girl, I didn’t get to see who the viewers were because it was just views on the Internet. So, one of the most amazing experiences was when we did the college tour. That’s when I first saw how diverse the viewers were and that made me very happy.

Kimberly White, FilmMagic courtesy of HBO
Kimberly White, FilmMagic courtesy of HBO

Sometimes it’s best to not go out of your way to try to please everyone.

I feel like you get lost if you try to do that.

I think of Insecure as your very own love letter to Drake.

[Laughs] That’s correct!

Obviously, Solange is involved and Pharrell was an early supporter of your web-series. I can totally see some famous faces coming on the show, maybe like in a dream sequence?

You’re spot on. We do have someone who shows up in a dream sequence who is an artist. It’s not Drake, though.

Is it Pharrell?

It’s not Pharrell.

Is it Kendrick?

Nope. [Laughs at the absurdity of me trying to guess].

Well, let me tell you, if anyone deserves a ride back home on HBO’s private plane, it’s you.

That’s what I keep saying.

Insecure airs Sundays at 10:30 p.m. on HBO.

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