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Issa Rae: "We Don’t Get To Just Be Boring"

The actress, showrunner, and comedian discusses the drive for diversity in television and finding her voice on HBO's Insecure.

Issa Rae: “We Don’t Get To Just Be Boring”

Awkward moment: A stint at Shondaland and talks with Larry Wilmore helped Issa Rae find her voice.

[Photos: The Collaborationist; stylist: Ayanna James; hair: Felicia Leatherwood; makeup: Kamaren Williams]

Issa Rae’s gawky-yet-relatable humor won her a throng of fans on YouTube and a place on best-seller lists for her memoir, The Misadventures of Awkward Black Girl. Here, she talks about her new HBO show, Insecure, why she loves Seinfeld, and the movement to diversify media.

In Insecure, you play a young woman who is just starting to deal with the realities of adulthood. What makes her tick?

She is complacent and used to doing what is comfortable, which makes her kind of passive-aggressive. She’s always wishing for stuff, but doesn’t take action. Then, there’s a moment where she’s just like, "Ya know what? I’m tired of coasting at my job and in my relationship. I want to be a different person." It’s about overcoming her own insecurities, and wanting to be . . . more.

Is that autobiographical? Your character is named Issa.

In my mid-twenties, I was comparing myself to peers, going to these Christmas parties where my Stanford classmates would meet up. I have a friend who was about to be a doctor, another who was a 25-year-old diplomat. They’d turn to me and they were like, "So, girl, I saw your YouTube video! Good job, girl!" [Laughs] Bless them for trying to pump me up, but it felt like, Is this what I’m meant to be doing?

[My character in Insecure] is definitely me at my core, but it’s not an autobiography by any means. I want people to watch it and feel like, "Oh I know that girl," or "I know that best friend," or "I’ve dated that guy," or "I’ve been in this situation!" I just want to create a relatable story that centers around black people being regular people.

What do you mean by that?

I don’t want to invalidate anybody’s black experience. But it seems to me [on television], we’re either extremely magical, or we’re extremely flawless. But we don’t get to just be boring. Like, it’s a privilege to be able to be boring and not answer questions like, "What do you think about this shooting?" and "How are you overcoming all of these obstacles?"

What about the times that I’m just kicking it with friends at brunch? Those are the moments that we want to reflect, in addition to talking about some of the issues that we encounter racially. That stuff plays in the background to our regular lives on the show, but we wanted to be in these characters’ worlds first.

What’s your favorite TV show?

I have so many. Of all time? I would have to say Seinfeld and Arrested Development . . . and Fresh Prince.

What do you like about Seinfeld?

The nothingness and the storytelling aspect. I get so much glee at the end of the episode when you realize how everything in it intertwines. Like, ohhh, haha, okay, that’s why that happened. It was so simple: about life and mediocrity and nothingness.

That ties back to what you said about minorities being able to have shows that are just about boring, daily life.

Can you imagine a black person pitching a show about nothing? "Wait, so there’s no struggle? There’s no race, there’s no—you’re black, though, right?" Like, we don’t get that. Only a white person could literally walk in the room and be like, "I wanna make a show about nothing," and they’d be like, "Sold!"

How did you make the transition from your YouTube series, The Mis­ad­ventures of Awkward Black Girl, to the very different world of television?

One of the biggest opportunities I got before HBO was [developing a pilot] with Shonda Rhimes and Betsy Beers at [pro­duction company] Shondaland. That was my first TV development experience. Shondaland really helped me figure out how strong my voice needed to be, and how certain I needed to be in it.

Who’s awkward now? Issa Rae’s bumbling, relatable humor has propelled her from YouTube to HBO.[Photos: The Collaborationist; stylist: Ayanna James; hair: Felicia Leatherwood; makeup: Kamaren Williams]

ABC ultimately passed on the pilot. What do you think happened there?

In my eager-to-please, "this is my only chance" mind-set, I wasn’t as firm as I should have been [in developing the story]. I wanted to tell a story about dating in L.A. I like to be raw, I like to curse, I like the N-word, I like portraying sex, and I like portraying the discomfort of stuff. I think that’s not really fit for network television. And because I wasn’t secure in the story, it was easy for me to flip-flop [on what I wanted]. And that’s not how you tell a story. When ABC ended up passing on the project, I was devastated, but I understood why. It was on me at the end of the day.

I thought that was my last chance. But then Casey Bloys and Amy Gravitt from HBO called the next month, and they were like, "Hey, we heard you’re free now. Do you have any other ideas that you want to explore?"

Did you do any soul-searching after the show wasn’t picked up?

Soul-searching? I did a lot of moping. [Laughs] I was just like, Ugh, what am I gonna do? Let me figure out my next moves on the web, because that’s always been consistent. Larry Wilmore actually helped me. Once I sold Insecure to HBO, they said, "You need a showrunner." [Wilmore came aboard to consult and cowrite the first episode.] He and I had a lot of conversations, and my soul-searching was saying things out loud, and learning from him and how firm he was in his voice.

He tells it like it is. How did you feel about Comedy Central’s decision to cancel The Nightly Show? You’d been a guest panelist there.

It’s their loss. It really plays to that thing that black [professionals] fear: That there is just one spot.

In addition to being executive producer for Insecure, you’re also a prolific YouTube producer. On your Issa Rae Productions channel, you’ve got both your own web series and projects from other creators. How did you get started?

I had acted throughout high school, but then I saw Love & Basketball when I was 16 and thought, Oh, I wanna write movies. I directed plays [at Stanford], then took some time off to learn filmmaking and writing at New York Film Academy. I created my first web series my senior year of college.

I began taking [the YouTube channel] seriously in 2009, with Fly Guys Present the F Word, which featured my brother and his music group in a documentary-type show. I start­­ed building an audience from there, and by the time I did The Misadventures of Awkward Black Girl [in 2011], we had 5,000 to 10,000 sub­scribers. The show took the channel to new heights. [The Issa Rae Productions channel now has 214,000 subscribers.]

Crossing over: Last year, Rae turned her YouTube series, The Misadventures of Awkward Black Girl, into a memoir.

And even though you’ve crossed over to cable, you’re still using YouTube to help the careers of others. For example, your #ShortFilmSundays channel features a new short film every week.

I’m a fan first, so I’m basically being a curator of content that I love. We put out a call, and we watch these short films and decide which writer/directors we want to highlight. We’re giving them a platform and then paying them a small fee to let us showcase it. We ultimately help to fund and share assets with creators. It’s community-building. We’re championing unheard voices for multiple mediums, and we aren’t afraid at all to look for new ones.

Which do you enjoy most, being in front of the camera or behind it?

Behind. A thousand, bajillion percent.

Why is that?

I just love telling the story more than being in the story. I think that plays true to my real life, too. I love listening to people more than I love talking.

We’re seeing a wider breadth of more nuanced shows led by people of color—Jane the Virgin, Fresh Off the Boat, Master of None, and now, Insecure. What’s the next step in making television more diverse?

It’s the executives, it’s the crew. It’s in making sure that this isn’t a flash-in-the-pan moment, by making sure you have a black or Latina executive, for example, who understands the importance of telling these stories. Making sure that everybody is represented behind the scenes is how the momentum will continue.

Prime time: Through Insecure, Issa Rae hopes to normalize the day-to-day lives of people of color.[Photo: John P. Fleenor/courtesy of HBO]

30-second bio: Issa Rae

Hometown: Los Angeles

Notable creative projects: The Misadventures of Awkward Black Girl, a web series that follows the professional, social, and romantic life of insecure black girl "J"; Fruit, a 10-part podcast drama about a pro footballer exploring his sexuality; The Peak, a content portal for the black intelli­gentsia; and Insecure, an HBO series that follows the professional, social, and romantic life of awkward black girl "Issa"

Big-name collaborators: Pharrell Williams, Shonda Rhimes, Larry Wilmore

On raising $714,000 through GoFundMe for the children of Alton Sterling, after he was killed by Baton Rouge police: "I realized how many other people felt helpless like I did. It’s a small step in trying to ameliorate a ter-rible issue."

First role: "I caught the acting bug in like the fifth grade when they cast my black ass as Demetrius, a man, in A Midsummer Night’s Dream."

A version of this article appeared in the November 2016 issue of Fast Company magazine.

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