Issa Rae talks about being ‘Insecure’ on HBO

This article was published in October 2016.

Her boyfriend is really kind of trifling. Her best friend is trying as hard as she is to find a great relationship. And at work, well, at work her co-workers just don’t quite seem to get what it’s like to be an insecure black woman.

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Issa Rae’s debut HBO show “Insecure” is a smart take on what it means to be on the eve of 30 with life not turning out quite like you expected. But this is a comedy and Rae has already proven she can spin black girl angst into black girl magic. She came to HBO’s attention after riding a wave of success with her web show, “The Misadventures of an Awkward Black Girl.” “Insecure” will debut its second season in the 10:30 p.m. time slot Sunday. 

Rae was in Atlanta last year at the Bronze Lens Film Festival to screen the pilot episode of the then new show. We sat down with her to talk about her journey from the web to premium cable, and about “that” rap.

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Issa Rae as Issa Dee in episode 2 of the television series “Insecure” created by Issa Rae and Larry Wilmore. (Anne Marie Fox/HBO/TNS) (The Atlanta Journal-Constitution)

AJC: What has it been like to switch from the web show “The Misadventures of an Awkward Black Girl,” where you had total control, to going to HBO with “Insecure”?

Rae: I’m so happy for the opportunity. It has been three years in the making. But I’m still producing content digitally. I’m still working with other indie content creators. My sensibilities will always be in indie.

AJC: But how much control do you have now that you’re with premium cable?

Rae: I’m completely in control of the narrative. I trust our showrunner (Prentice Penny). And HBO is great with stories. Culturally, they get out of the way. They trust us.

AJC: I have to ask, where did the freestyle rap you did with the hook line that we can’t print come from?

Rae: It really came from a conversation with my best friend and I. She was talking about the struggle of being out there single. And I told her, “It really might be broken.” I was telling (“Insecure” co-creator) Larry Wilmore that story and he was cracking up. He was like, “That needs to go in the pilot.”

AJC: So how do your friends feel about that because they say a writer should pull from what she knows and what she’s lived through, but that can put people’s business out there?

Rae: They say don’t date a writer, that you shouldn’t be friends with a writer because you’re going to end up on the screen and on the page. That’s very much true. I don’t do it on purpose but in order to tell a real story, you draw from real moments.

AJC: Talk about some of the influences you had over the years on your writing and your comedy.

Rae: Definitely the ’90s. “Living Single,” “Martin,” “The Fresh Prince of Bel-Air,” “Moesha,” “Girlfriends.” Seeing regular black people and seeing varied voices. But also loving Larry David and “Seinfeld” and Tina Fey and loving that kind of sense of humor but not being able to see people of color in it. It’s like, “I laugh at this. I find it funny and my friends find it funny, so why are there segregated senses of humor?” I wanted to kind of blend the two.

AJC: But how do you make sure people are laughing with you and not at you? Remember that was the crisis Dave Chappelle faced. He was worried that white audiences had begun to look at him as some kind of minstrel and he didn’t want his humor perceived that way.

Rae: For me it’s about making sure that everybody behind it is of color, and then I feel fine about it. It’s not like white people are on my team exploiting me. It’s like we’re making this together and it’s very much an authentic project. As long as we’re secure in the story we’re telling, I don’t care how you interpret it because we know where it’s coming from.

AJC: What should we expect from your character going forward?

Rae: It’s really just a story about learning to be confident in your insecurities. Which is a place that I’ve gotten to, where I’m like you know what, I know what my flaws are I know what I’m insecure about but I’m confident that that makes me who I am, and I’m happy with who I am. Seeing that character learn to be comfortable with herself is really the journey of the story.

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AJC: Besides “Insecure,” what are the three shows you’ll be watching this and upcoming seasons?

Rae: “Atlanta,” amazing! “Queen Sugar” by Ava Duvernay and Gina Prince Byethewood’s “Shots Fired.” I love (Byethewood) she’s a big influence for me. “Love and Basketball”? Yeah!

AJC: What has been the best part of the transition from the web to cable?

Rae: Being able to have my team alongside me and being able to bring in other people that were with me early on along for the ride. That’s the best part.

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