'Awkward' And 'Insecure' Get To The Root Of Writer Issa Rae's Humor

Sep 3, 2018
Copyright 2018 Fresh Air. To see more, visit Fresh Air.

TERRY GROSS, HOST:

This is FRESH AIR. I'm Terry Gross. Today we conclude our series of interviews with current Emmy nominees. The ceremony is Monday, September 17. We start today's show with Issa Rae, the creator and star of the HBO series "Insecure." She's nominated for outstanding lead actress in a comedy series.

"Insecure" echoes the title of her memoir and Web series, which were both called "The Misadventures Of Awkward Black Girl." In all those works she's dealt with issues of identity and feelings of not fitting in, things she dealt with all the time when she was growing up. She was one of the few black kids in her high school in Maryland. But when her family moved to South LA, she wasn't considered black enough. She's also lived in Senegal, where her father is from, where she was the only American in her school.

Let's start with a clip from the current season of "Insecure," Season 3. Issa and her boyfriend have broken up, and she's staying with her ex-boyfriend Daniel. She wants to get her own apartment but can't afford to. So she goes to the office of her accountant friend, Kelli, hoping for financial advice. Issa gives Kelli some financial papers, including her credit report, which is bad.

(SOUNDBITE OF TV SHOW, "INSECURE")

ISSA RAE: (As Issa Dee) My credit score can't be that bad.

NATASHA ROTHWELL: (As Kelli) Bad would be a step up. The basic credit tiers are excellent, good, poor, bad. This is Issa. It's all the way at the bottom. Look; I'm sorry. There's no way to get around this credit issue unless you get a co-signer - not me - or you could put down three or four months' rent if you've been saving.

RAE: (As Issa Dee) Oh, I have been saving.

ROTHWELL: (As Kelli) OK.

RAE: (As Issa Dee, singing) I've been saving. I've been saving, I've been saving.

ROTHWELL: (As Kelli, singing) Ay, ay, ay, ay (ph).

ISSA RAE AND NATASHA ROTHWELL: (As Issa Dee and Kelli, singing) I've been saving.

ROTHWELL: (As Kelli, singing) She's been saving, she's been saving. Ah, ah, ah. Uh-uh, uh-uh. Uh-uh.

RAE: (As Issa Dee) No, you know I eat out a lot.

ROTHWELL: (As Kelli) Oh, girl. Lids?

RAE: (As Issa Dee) I like my caps fitted.

ROTHWELL: (As Kelli) That is just - RadioShack ain't even a store no more. Rite Aid? You buying groceries at Rite Aid?

RAE: (As Issa Dee) I buy panties there, too.

ROTHWELL: (As Kelli) Warren, close the door.

RAE: (As Issa Dee) What? Girl, come on. I've been working a full-time job. I've been lifting. What else can I do?

ROTHWELL: (As Kelli) Look; long term, I could set you up with a credit counselor here. And I will help you plan out a budget. But right now you don't have enough money to move out on your own.

RAE: (As Issa Dee) Kelli, I got to do something. I told Daniel I'd only be staying there a few weeks, and I don't want to take advantage of that.

ROTHWELL: (As Kelli) Well, if it'd make you feel better, then you could throw him a few extra bucks.

RAE: (As Issa Dee) Oh, yeah. You know, he's not charging me to stay.

ROTHWELL: (As Kelli) I'm sorry, what?

RAE: (As Issa Dee) He not charging me to stay.

ROTHWELL: (As Kelli) He not? You concubining (ph)?

RAE: (As Issa Dee) What? Kelli, no.

ROTHWELL: (As Kelli) Not even a little bit?

GROSS: In this season of "Insecure," Issa has become even more disillusioned with her job at a nonprofit which works with predominantly African-American schools mentoring and coaching students. When I spoke with her in 2016, we played this clip from the first episode in which Issa's talking to a class of junior high students.

(SOUNDBITE OF TV SHOW, "INSECURE")

RAE: (As Issa Dee) As youth liaison, I can assure you that whatever it is you need to succeed, we got y'all. So do y'all have any questions? Don't be shy, guys. Fire away.

UNIDENTIFIED ACTOR #1: (As character) Why you talk like a white girl?

(LAUGHTER)

RAE: (As Issa Dee) You caught me. I'm rocking blackface (laughter). Any other questions?

UNIDENTIFIED ACTOR #2: (As character) What's up with your hair?

RAE: (As Issa Dee) I don't know what you mean.

UNIDENTIFIED ACTOR #2: (As character) My cousin can put some tracks in it unless you like it like that.

UNIDENTIFIED ACTOR #1: (As character) You're rude. She African.

(LAUGHTER)

RAE: (As Issa Dee) We're all from Africa, guys

IVAN SHAW: (As Justin) Absolutely. Let's stick to questions about the program.

UNIDENTIFIED ACTOR #3: (As character) Is this what you always wanted to do?

RAE: (As Issa Dee) No. But I got this job after college, and it fit my interests at the time.

UNIDENTIFIED ACTOR #4: (As character) Are you single?

RAE: (As Issa Dee) I don't think that's appropriate.

UNIDENTIFIED ACTOR #4: (As character) Yeah, she's single.

(LAUGHTER)

RAE: (As Issa Dee) OK, since you guys are so interested in my personal life, here it is. I'm 28 - actually 29 'cause today's my birthday. I came from a great family. I have a college degree. I work in the nonprofit world because I like to give back. I've been with my boyfriend for five years. And I did this to my hair on purpose. So I hope that covers everything. Does anybody actually have any questions about We Got Y'all?

TIANA LE: (As Dayniece) Why ain't you married?

RAE: (As Issa Dee) I'm just not right now.

LE: (As Dayniece) My dad said ain't nobody checking for bitter-ass black women anymore.

(LAUGHTER)

SHAW: (As Justin) Dayniece, that's detention. Apologize now.

LE: (As Dayniece) Sorry.

RAE: (As Issa Dee) That's OK. And tell your dad that black women aren't bitter. They're just tired of being expected to settle for less.

UNIDENTIFIED ACTOR #3: (As character) Her outfit settled for less.

(LAUGHTER, SOUNDBITE OF ARCHIVED BROADCAST)

GROSS: (Laughter) That's Issa Rae from the first episode of her series "Insecure." Issa Rae, I love the series. Welcome to FRESH AIR.

RAE: Thank you so much, Terry.

GROSS: You really set the tone in that scene. I mean, you work for this nonprofit that - you're the only African-American at that organization. But when you get in front of, like, the African-American students - and I forget if it's junior high or high school...

RAE: Junior high.

GROSS: Yeah. So they just start, like, mocking you, you know, like, your hair, the way you speak, that your clothes - (laughter) they don't like your clothes. You're not married (laughter). So I just think it's so interesting that you start the series off with discomfort coming at you from both the white people that you work with and the black kids that you're trying to help.

RAE: Yeah, we wanted to kind of paint that this character is in between two worlds and is just in a constant state of discomfort. And, you know, that is kind of reflected in the title of the series. But just in terms of her own experiences - you know, not black enough for the black people and not, you know, white enough for the white people.

GROSS: So the things that your character is mocked for by the junior high school kids - where do those lines come from? Did kids in junior high say that to you?

RAE: Yes. Pretty much everything aside from the why aren't you married part I've been asked. Actually, in my adult life I've been asked, why aren't you married? What am I talking about?

GROSS: (Laughter).

RAE: But all of those questions those kids asked I've been asked at some point in time. So that was all truth. And we just wanted to have her face all of those questions at once in a very irritating way.

GROSS: So let's hear a scene at work. So this is from the start of the series where you're describing the nonprofit that you work at, which is called We Got Y'all. And you're talking about the organization. And as you are doing this kind of voice-over thing, we see images of where you work, and we see your white boss wearing a dashiki. The office is full of posters of Martin Luther King and Beyonce and a photo of the boss with President Obama. And at the end of this voice-over, it cuts to you. And you're in front of a mirror. And you're rapping in front of the mirror. In the series, this is the equivalent sometimes of your voice-over narrative - you know what I mean? Like, you're talking to yourself, but you're doing it in rap. So that's how the scene ends, but it starts with a voice-over.

(SOUNDBITE OF TV SHOW, "INSECURE")

RAE: (As Issa Dee) My boss founded a nonprofit to help kids from the 'hood, but she didn't hire anybody from the 'hood.

CATHERINE CURTIN: (As Joanne) I'm torn between the Booker T. method and the DuBois method. What would James Baldwin say is most beneficial for people of color?

RAE: (As Issa Dee) In 2016? I've been here five years, and they think I'm the token with all the answers.

VERONICA MANNION: (As Kitty) Let's just ask Issa. Issa, what's on fleek?

RAE: (As Issa Dee) I don't know what that means. I know what that [expletive] means. But being aggressively passive is what I do best. I used to keep a journal to vent. Now I just write raps. (Rapping) Go shawty (ph), it's my birthday. But no one cares 'cause I'm not having a party 'cause I'm feeling sorry for myself.

GROSS: OK, and you rap much better than that later...

(LAUGHTER)

GROSS: ...Later in the series.

RAE: Do I?

GROSS: Yes. In my opinion, yes.

(LAUGHTER)

GROSS: So part of this series is about, you know, being the person who you think is, like, the token black person at work. And your best friend is the only African-American in the law firm where she works. She's a lawyer. So did you have - I mean, being an artist, like, you're working on TV shows. And this is, like, your own show. It's, like, your creation. Did you work in a nonprofit where you felt similar to how your character does?

RAE: Absolutely. I've worked in a couple of nonprofit settings. I've worked in - briefly in the corporate world and have definitely been the sole person of color, the sole black person. And for me, with this organization in the series, We Got Y'all, I really wanted to just depict my nightmare nonprofit organization. I found the world of nonprofits funny to begin with just because having worked there, you see that people are so altruistic and they're so benevolent and they're pretty selfless and you're working generally for a great cause.

But the atmosphere within the work environment can be oddly competitive. People want the credit. Sometimes they don't listen to the people they're trying to help. And for me, this white guilt is so prevalent at this nonprofit. And they're so - they treat the kids as this pity party. And for me, I would hate to work in an environment like this, but it's ripe for comedy.

GROSS: So let me ask you about the Web title "Awkward Black Girl." That's how you saw yourself for a long time. Where did the awkward part come in - which I imagine is the same kind of part that your series takes its name from, "Insecure."

RAE: Yeah, well, I was sitting on my bed in New York one day and just thinking about - just having a reflective moment and trying to figure out what I wanted to do and what my issues were and just was writing in my notebook and wrote down the phrase, I'm awkward, period, and black. And that was just a revelatory moment for me in so many ways. Like, I knew I was black obviously, but the awkward part really just defined me, in a sense.

Like, it defined why I was always, like, socially uncomfortable. It defined my introvert status. It defined, like, why I didn't fit into mainstream media's definition of blackness. And I just thought that that felt like an identity that I had not seen reflected in television or film before or at least in a very long time, not since the '90s with side characters. But I'd never seen, like, a lead black girl just be awkward.

GROSS: So what made you think that the parts of your life that made you feel awkward and insecure you could claim as an identity and then use that to your advantage and create a character who would be kind of, like, funny and relatable and everything, and that - so you could turn what you perceived as, like, your weakness into a strength?

RAE: Well, for me it came from watching shows like "Seinfeld" and "Curb" - "Curb Your Enthusiasm" - and even "30 Rock" and just identifying with a very specific sense of humor that those shows had but also being like, wow, there are no people of color in these shows that have the same sense of humor, you know? And wondering, like, why is there this segregated humor? There seems to be, like, black humor, and there seems to be white humor. And, you know, a lot of my friends' tastes - you know, we like both, but we don't get to see ourselves reflected on the, quote, unquote, "white humor" side.

And so I wanted to take these traits in the same way that, you know, a lot of my favorite comedians have done it, Ellen included - Ellen takes so many relatable, embarrassing moments and amplifies them and makes it like oh, my God, I've been through that, too, and that's so funny - and have a black character go through those things, and make it very racially specific but universal at the same time.

GROSS: We're listening to the interview I recorded with Issa Rae, creator and star of the HBO series "Insecure." She's nominated for an Emmy for outstanding lead actress in a comedy series. We'll hear more of the interview after a break. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. Let's get back to my interview with Issa Rae, creator and star of the HBO series "Insecure." She spent part of her childhood in Maryland, where she was one of the few black students in her elementary school. When she moved to LA, she went to a predominantly black junior high school. She told me it was a bit of a culture shock.

(SOUNDBITE OF ARCHIVED BROADCAST)

RAE: It was just because I was watching a lot of television. So I watched shows like "Saved By The Bell." Even though that wasn't set in LA, I just thought that would be my LA experience.

GROSS: (Laughter) That's hilarious.

RAE: And "90210." (Laughter) And just was excited to be able to go to junior high and have lockers. Like, there was just something sexy and alluring about lockers to me. And there was a culture shock in that way, that I was not the popular girl, that no one cared that I came from Maryland, that I was just not - you know, people always said that I talked like a white girl. And my hair wasn't - did not have the positive traits it had for being natural like it did when I was in Maryland. And I was just, like, out of place. And, you know, I think part of that was also that I was a nerd, too. But I just remember thinking like whoa, I do not fit in. And I wonder why that is. And it's a period of time that I always reference in my work, I find.

GROSS: What was your father's attitude to the whole American thing about what it means to be black and are you black enough and are you authentic and all that? 'Cause coming from Africa, I'm not sure whether all of that would have made any sense to him.

RAE: It didn't. And he didn't really subscribe to those notions. I mean, he understood that there are obstacles that black people faced, but in his mind, those are obstacles that you can overcome just by working hard and by doing the right thing. And we've never really had conversations about race just because, you know, while he acknowledges a lot of the burdens, he's also like his own success story.

You know, he came from a family of, you know, seven kids - the oldest - and came from Dakar, Senegal, and is a successful doctor here. And so he's just, like, very much about working hard. And in some ways, I realize that in not having those discussions with him and just seeing what he's done, I've been able to kind of do that on my end, too. Like, I do refuse to see obstacles to a degree. And, you know, I acknowledge that they exist, but I refuse to kind of let them affect me. And I guess I'm just realizing that about him.

GROSS: You write that the first time in your life you ever felt beautiful was when you went back to Senegal when you were in your sophomore year of high school and that that was the first time you had boys and men pining after you. (Laughter) Were you considered more beautiful in Senegal than you were in LA?

RAE: Yeah. I think when you're in a country of people who look like you and have your features and who are married to people with your features and attracted to, it makes it a lot easier. But, I mean, I just grew to appreciate where I came from more and felt also appreciated in a way that I did not in Los Angeles, Calif.

GROSS: So when you were a kid and watching TV and not exactly seeing yourself represented, you were sending in scripts at a really young age, like, spec scripts. Like, what kind of kid were you (laughter) that you were sending in scripts?

RAE: Yeah, I mean - I will say that - well, when I was a kid, I did have - like, the '90s gave me everything. You know, we had "Fresh Prince." We had "Living Single." We had, you know, all these shows. And it was when I got to I think high school and college that I didn't see myself represented. And when I was younger, like, I felt like I wanted to be a part of the writer's rooms. I wanted to write my own show. And so, like, I remember the show "Cosby" came out, which was a different iteration of "The Cosby Show," and I sent in a script for that.

And I remember going to my first live taping of a show in LA when we moved back when I was 11 - it was "Moesha." And I got to be in a live studio audience and watch what I say was the last, like, regular black girl we had on TV, Moesha - regular lead black girl we had. And I remember just sitting in that audience, taking it all in and loving it. And then I want to say that I won a copy of the script for that episode. And it was pink, and I still have it in a box somewhere. But that script is tattered because I would always use that as, like, the template to write scripts. And so when I wrote my "Cosby" spec script, and when I wrote my original spec script, like, it was always based on that format and...

GROSS: What did you learn by studying that script so carefully?

RAE: I mean, three-act structure, just how - obviously, it was a shooting script so I didn't understand that at the time. So there were so much - there was a lot of lingo that I just didn't get. But for me, it just felt, like, doable. It was like, oh, my gosh. I have the key. I have the secret of how it's done. And the formula is at my fingertips. And I just remember rereading to see like, oh, OK, this was - there was sort of a cliffhanger before this commercial break. So I need to have that in my own script. Or there was a significant plot device for character A but not on the B story. So just, like, really trying to break it down in a way that was familiar to me in watching so much TV. And, of course, I have no doubt that my own scripts were terrible. But it just felt like, oh, I could do this.

GROSS: How did you know who to send the scripts to?

RAE: (Laughter) My grandmother was great about, you know, helping me to research. She was very computer-savvy. And I remember, you know, typing the scripts on her Mac computer and her teaching me how to copyright them and teaching me to, like, Yahoo the head of NBC. And for me, it was just, like, writing a cover letter to who I saw was the head or the president of NBC. And I remember getting some notices back like...

GROSS: Wait. You wrote to the president (laughter) of the network?

RAE: Yeah. But, of course, from NBC being like, hey, thanks for submitting, but we don't take unsolicited scripts.

GROSS: From children, yeah.

(LAUGHTER)

RAE: Yeah. From babies, yeah.

GROSS: So I listen to a lot of voices (laughter) in hosting the show. And I love your voice. You have a beautiful voice. It's so, like, deep and resonant and...

RAE: (Laughter).

GROSS: So when you were like...

RAE: Thank you.

GROSS: ...How old were you when it started to get that kind of, you know, depth, that resonance? You didn't have that in high school, did you?

RAE: Geez. I don't know. I don't - I do not know. It's so funny - this generation - I was saying, we're so used to seeing ourselves and listening to ourselves now that it's just not a big deal. But I remember being - like, hearing my voice on a voicemail and being like, ugh, stop it. Make it stop.

GROSS: (Laughter).

RAE: And, you know, now I just don't even think about it. So I've always thought I had a deep voice since high school, middle school, but I have no idea. But thank you.

GROSS: It's interesting because your voice conveys a certain confidence that you say that you've lacked in real life.

RAE: That's helpful.

GROSS: (Laughing).

RAE: That's very helpful. Well, that might be why people don't think that, I mean - people are always like, oh, it's so funny that you say that you're awkward 'cause you're not. And I'm like, 'cause I fooled you. But I don't - I don't see the same. I don't see what they see.

GROSS: Issa Rae, it's been great to talk with you. Congratulations on your series.

RAE: Terry, it's been an honor. Thank you so, so much.

GROSS: Issa Rae created and stars in the HBO series "Insecure." Our interview was recorded in 2016. She's nominated for an Emmy for outstanding lead actress in a comedy series. After a break, we'll feature interviews with two more nominees, Trevor Noah, host of "The Daily Show," and Peter Morgan, creator of the series "The Crown." I'm Terry Gross, and this is FRESH AIR.

(SOUNDBITE OF SONG, "FINE LINE")

JORJA SMITH: (Singing) I see you smiling as you're talking on the phone. Hiding your messages, but I already know that I'm not a part of your game. It ain't right what you're doing to me. It ain't right. You're confusing me. Which side of the fine lines do you want me?

(SOUNDBITE OF MUSIC) Transcript provided by NPR, Copyright NPR.