Issa Rae on the ‘Insecure’ Moment That Destroyed Her Mentions

The multi-hyphenate talent on life in the writer’s room and why she doesn't want her show to have any “Trump stench.”

Issa Rae Independent

Actress Issa Rae attends the 2017 Film Independent filmmaker grant and Spirit Award nominees brunch at BOA Steakhouse on January 7, 2017 in West Hollywood, California.

Issa Rae Independent

We don’t deserve Issa Rae. The 32-year-old continues to collect hyphens (currently: actor-producer-writer-director) but is still down to rap about what she’d do for the D. Rae’s radical relatability is exactly what makes her so easy to root for. Hell, even Michelle Obama is a fan.

And the accolades continue to stack. In just this year, Rae wrapped the second season of Insecure, was named the new face of CoverGirl, secured a role in her first film with The Hate U Give, began development on a '90s drama with HBO, and became the first Black woman to create and star in a premium cable series. She’s also maintained a steadfast commitment to championing women and people of color (see: her incredible Emmys moment, her excellent takedown of white male privilege).

Rae’s latest initiative is happening on an unlikely stage: at Miami’s Art Basel, where Rae will host the finale of Bombay Sapphire’s eighth-annual Artisan Series—a nationwide competition to discover multicultural artists.

“Similar to the entertainment industry, there is such an immense pool of undiscovered and diverse artists who oftentimes are not given a platform to showcase their talent,” Rae explained.

Complex spoke to Rae about her ongoing efforts to advocate for POCs, what her future talk show look might look like, and the Insecure moment that left her mentions in shambles.

This interview has been lightly edited for clarity.

You have a long history of advocating for women and people of color, from the ColorCreative initiative to your current work with the Artisan Series. What drew you to take on this particular project?
Absolutely that. I’m pretty limited to film and television and those kind of mediums, so visual art is just something that I’ve been intrigued with because there are so many different interpretations and it is arguably so much more personal than a medium like TV and film. So to be able to champion emerging artists in this field is so cool to be able to do.

Whether you’re seeking out a producer, a writer, or in this case, an artist, what do you look for in a new talent? What makes you say, “Hey, this person’s got it”?
One is passion. There is nothing worse than meeting somebody that is like “Yeah, I do this, I’m just good at it.” There is something about passion and purpose that you look for in someone. Why did you want to do this piece and why did you want to tell this story? What does it mean to you specifically?

And then uniqueness—is this something that I have seen before? You can be passionate but your idea could be beat into the ground by someone else. I just want to know what are you introducing me to that I am not familiar with. So those are the two things that I’m looking for.

As a woman of color, you’ve probably dealt with a good deal of sexism and racism. What would you say to young creatives who encounter these types of roadblocks?
In my own mind, I have to push past it. There is nothing that fuels me more than being doubted. That’s my drive; that’s when I become unstoppable. Like, “Oh you think I can’t do this?” or “Oh, I’m beneath you?” Well, I’m just going to prove you wrong. It’s very much a silent fight, and I’m just like, “Bring it on.”

Insecure has been a catalyst for a lot of tricky conversations around sex, relationships, and race. When you write the show, do you purposely set out to be controversial and shock people?
No, not at all. In the writers’ room, we talk about our lives and have debates and arguments and stay true to our stories. Even today, talking about a specific storyline, we never want to take a specific stance. We always just want to start conversations that live in the grey area of things. I think that’s where things are most interesting—when we are just like, this is something that we all go through but have different views or interpretations of. I think that’s what art is and should do.

With respect to the sex scenes on Insecure, where do you find inspiration for some of the crazier situations, like Lawrence’s racist threesome? That’s some of the craziest shit I have ever seen on television.
That’s funny—that was another thing inspired by the stories. I had friend that went through a similar situation of meeting two girls at a grocery store and getting into a threesome and not being able to perform fully. We were like, this would be such an interesting story for Lawrence to go through—but how could we take it a step further? How could we add the racial element and add the weight of him being a black man in this particular situation?

So we will take real life stories and add our specific characters and show spin, because we are exploring the lives of black millennials at the end of the day. While we don’t think every subject, every storyline, should have a racial element, that is kind of what makes our show and it is kind of life. Race is always sitting in the background, and that’s what our inspiration comes from.

The writing staff on “Insecure” is mostly comprised of women. How does that help your creative process? Obviously, the world is really crazy right now—it must be awesome to have fewer men to deal with.
[Laughs] I remember sometimes we would split into rooms to focus on episodes. One room would focus on episode one and another room would focus on episode two. And when we split rooms we realized—and it would just be random—we realized it would just be women. One of our guy writers actually happened to be out of town, and it was literally the week when bombshell after bombshell, dude after dude was being taken down.

We just found ourselves sitting in there, talking about it and telling our own personal stories in the way that only female comedy writers can, finding the humor in it. It was an honest and real conversation amongst women. And it was so comforting to realize we were all on the same page and there for each other. It’s refreshing.

You’ve tackled lots of important issues for women on the show, like the wage gap. On season 3, are we going to see the current news climate reflected in the show?
Not in a way that you’ll know right off the bat. I always say there are elements of the news climate that our show would address anyway. But then anything that’s political, I don’t want it to feel dated. I don’t want it to have the stench that, God willing people are watching this years down the line, it feels like “I know what they were talking about then,” or “This has nothing to do with anything that’s happening here, so this show doesn’t feel relevant to me.”

Bottom line is, I just don’t want any Trump stench on this show, period.  But things outside of that, anything that feels culturally or socially relevant at this moment, you’re going to see it in the show.

Our readers loved the Drake and Frank Ocean easter eggs in season one and two, respectively. Is there an artist you’re really into right now who might pop up in season three?
I would never give a clue! But to be honest, I don’t even know yet. I don’t even know if I want to do easter eggs. I might want to do something different. It may even align with what I’m doing right now—what I’m talking to you about. I’m just having fun with it.

Issa’s mirror raps are one of my favorite parts of the show. Do you think you’ll ever pull a Donald Glover on us and drop a full mixtape—or at least a guest verse?
I think I know my place. Donald Glover raps really, really good. He’s a master of all trades. So, no. That’s the answer.

This past summer, you starred in Jay Z’s “Moonlight” video. How did that come together? Did Jay reach out to you?
Not personally, but I guess to my people. I was shooting Insecure at the time, but I was like, nah, we are going to make this work. Either cancel today or I’m not going to be here—but whatever we need to do, let’s make it work. It was hard to make happen but that’s the kind of thing where you drop everything, especially when you hear about who else is going to be in it. That’s the first time I met Tiffany Haddish, and I had heard her name for so long. That was the beginning of our friendship. It was just a great, great opportunity.

If you had a chance to do a cameo again, which one artist’s video would you want to be in?
Beyoncé. Rihanna or Beyoncé. Either one.

Your “I’m rooting for everybody black” response on the Emmys red carpet is one of the most iconic moments of 2017. It’s so sad that there are still so many “first black woman this,” or “first black man this.” Is there any role that you have in mind like, “I’m going to come for that spot and I’m going to be the first?
Ahh man, I don’t really think about it. It’s always a surprise. I was hearing Lena Waithe was the first black woman to win a comedy writing award [Waithe’s Emmy victory in 2017 for co-writing Master of None's “Thanksgiving” episode marked the first time a black woman had won the trophy for writing in a comedy series]. I didn’t even know that was a thing.

There are so many things where it’s just like I am going about my day, like even being the first [Black woman] to create and star in a premium cable comedy series—those are things that you just don’t know. I just have so many goals and things I want to happen. When it first happens it’s kind of bittersweet—like “Oh cool...What?” So that’s really my reaction to everything like that.

You were recently called a “mini-Oprah” by Larry Wilmore. I thought that was a really on point comparison. If you were able to host your own talk show, what would that look like?
Oh man. It would be a lot of shit talking, a lot of alcohol. It would have a lot of my friends within the entertainment industry and outside of the entertainment industry just talking about everything. That would be fun, but I think the alcohol would be the most important thing.

Did Chelsea Handler have alcohol on her show?
I think so. I never got to be on it, and wanted to go on it just for that. I made a promise to myself that the next press tour I do for Insecure, I will be intoxicated.

There’s a passionate community around Insecure on Twitter. Is there a specific moment on the show that most destroyed your mentions?
A thousand percent the cum in face episode for just so many reasons. That was just one of those times where I was like, I’m going to take a break this week.

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