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


This is FRESH AIR. I'm David Bianculli, editor of the website TV Worth Watching, sitting in for Terry Gross. Today's first guest, Issa Rae, is the star and co-creator of an HBO comedy series that begins its second season on Sunday. It's called "Insecure." And that title gives a strong hint about Issa Rae's self-image and her comic perspective. So does the title of her web comedy series that preceded "Insecure." It was called "The Misadventures Of Awkward Black Girl."

Both series are about issues of identity and feelings of not fitting in, things Issa Rae dealt with when she was growing up. She was one of the few black kids in her school in Maryland. But when her family moved to South LA, she wasn't considered black enough. And before that, when she lived in Senegal, where her father is from, she was the only American in her West African school.

Rae co-created HBO's "Insecure" with Larry Wilmore, and she stars in it as a 29-year-old woman whose life seems to have stalled. Terry spoke with Issa Rae last year. As the series began last season, she was living with her boyfriend but unsure about both her relationship and her job. She was working as the youth liaison at a nonprofit called We Got Y'all, which sponsors mentoring programs, afterschool tutoring and test coaching in predominantly African-American schools.

Here's a scene from last season's opener.


ISSA 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 way.

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


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

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

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

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

UNIDENTIFIED CHILD #1: (As character) You're rude, she's African.


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

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

UNIDENTIFIED CHILD #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 interest at the time.

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

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

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


RAE: (As Issa Dee) OK, since you guys are so interested in my personal life, here it is. I'm 28 - actually 29 because today is 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.


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


TERRY GROSS, BYLINE: (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, like just in terms of our own experiences - you know, not black enough for the black people and not, you know, white enough for the white people. So initially that scene was in the middle of the script. But in editing, we decided to put it at the front just because - or to make it the opening scene just because it really identified - you know exactly who she is when you see that first scene.

GROSS: Just another thing I really love about that scene is that you're being insulted for things you're proud of - you know, your hair, the way you speak - and you're being insulted by children, a big group of them. And they're kind of, like, ganging up on you. Have you ever been in that position? I mean, I have when I taught briefly.


GROSS: It was just really awful to supposed to be the adult in the room and, like, the kids are just, like, mocking you. And...

RAE: Kids are so good at that, though. They're so witty. And especially at that age - they're, like, 11 or 12, so it feels like their sense of humor is just getting honed. And it kind of gets mean to that point, like they're trying to one-up one another to be the funniest.

And in hindsight, I'm just like, they were funny. They were really, really funny kids. But it hurt my feelings.

GROSS: Can we get to some of the things they insulted you for?

RAE: Definitely my hair. I remember one girl saying to me just that nobody should fight me because I would probably take something out of my nappy hair and throw it at them, like I was just hiding weapons in my hair. They were really funny, though. They were just jerks, but they had a very specific sense of humor.

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 voiceover 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 voiceover, 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 voiceover narrative, you know what I mean? Like, you're talking to yourself, but you're doing it in rap. So that's how this scene ends, but it starts with a voiceover.


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

LISA JOYCE: (As Frieda) 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) 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.

Go shorty, it's my birthday. But no one cares because I'm not having a party 'cause I'm feeling sorry for myself.

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


GROSS: ...Later in the series.

RAE: Do I?

GROSS: Yes. In my opinion, yes (laughter). So part of this series is about, you know, being the person who you think is, like, the token black person at work. And...

RAE: Right.

GROSS: ...Your best friend is the only African-American in the law firm where she works. She's a lawyer. So did you - 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 to pick 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: And she's in the - your character's in the position of having, like, a great Kenyan leader quoted to her by a white person. And the white person is sitting - sitting down your character, saying, like, you've got to work harder. You're not really - you don't seem to be invested in the work anymore. And she says, you know, if you're not invested in the work, maybe this isn't the place for you. And then she quotes this great Kenyan leader as saying, the leader who doesn't take advice is not a leader. And your character's kind of rolling her eyes that, you know, she's getting this Kenyan quote quoted back at her. Is that something that you've experienced and that bothers you when it happens?

RAE: (Laughter) No one's quoted a Kenyan proverb to me, thankfully. But I have had, you know, people - and in this scene, it's kind of hard because the boss isn't wrong. Like, you know, Issa has not been putting herself out there. And I have been called out for just not being present, and that's been correct, you know? I was working at jobs that I knew that I didn't want to be at long-term because I wanted to pursue my dreams.

But - and then conversely, I have had, you know, white people kind of try to take my black card, in a sense, and use examples of "mainstream blackness," quote, unquote, and use me as a reference for why I don't act black. And that's been extremely frustrating, just to be like, whoa, how are you going to, in your limited definition of blackness, try to paint me as non-black? It's kind of absurd.

GROSS: If you're just joining us, my guest is Issa Rae. And she created and stars in the HBO series "Insecure." We're going to take a short break here, then we'll be right back. This is FRESH AIR.


GROSS: This is FRESH AIR. And if you're just joining us, my guest is Issa Rae. She's the creator and star of the HBO series "Insecure." And before that, she created and starred in the web series "The Misadventures Of Awkward Black Girl."

So it seems to me you have a very complicated relationship with rap, starting with when you moved to south LA after having grown up in Maryland and having gone to a predominantly white but multicultural, you know, kind of diverse school in Potomac, Md. You had also lived for a while in Senegal. Your father's from Senegal. So when you moved to south LA, what did rap mean to the students in your school there, and how much did you - like, how much did you know about the music when you moved there?

RAE: I only knew what my older brothers - so I have two older brothers, and they were super into hip-hop, rap. And they would try to introduce me to artists. But I was more into R&B and just pop music in general. And I was young, and my mom shielded me specifically and my younger siblings from, like, explicit lyrics and explicit music in general. So they could introduce me, but I didn't really - I didn't really pay attention. And so by the time I moved to LA, I was great. I was really well-versed in R&B. Like, nobody could touch me there. But I wasn't as into rap as a lot of the other students.

And I remember the year that I started sixth grade Tupac died. And I didn't know much about him. And obviously, Tupac and LA are - go hand in hand to a degree. Like, LA claims claims Tupac really hard. And I didn't know him, so when everyone was devastated that he died, you know, I wanted to be part of the conversation and had only read his name and hadn't heard it. And so I came up to a bunch of classmates who already did not like me already and was just like, oh, my God, I heard that Tupac died? You know, what did he sing - and was just shunned for the rest of the quarter.

GROSS: When your character raps in the series in an early episode, she's - I'm going to keep this really clean for the radio...


RAE: Good luck.

GROSS: The rap is about a woman's privates, which is a popular subject for a lot of rap music.

RAE: So unfair.

GROSS: (Laughter) But this is more from a woman's point of view of somebody whose privates have kind of had enough. And so - and then later on, your character's listening to a male rapper in a recording studio, who's just doing this really - just kind of - just misogynist kind of filthy rap (laughter). It's an interesting contrast between the two. But did you see yourself as taking that kind of explicit rap lyric and doing it from, like, a woman's point of view?

RAE: I saw it as just doing something very raw. And, yeah, I mean, I think that the P word, which is used, is something that up until recently, up until Donald Trump came around, we were, like, shying away from and was always seen as vulgar or, like, claimed by men. And I kind of wanted to reclaim it for women and kind of force you to bump this song, to like it and to get it stuck in your head. But that conversation about a woman's nether regions is actually one that I've had with my very close friend.

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 being - 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's - 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' taste - 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: So when you got to LA, was it a bit of a culture shock from Maryland?

RAE: It was just because I was watching a lot of television, and 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. And "90210..."

GROSS: (Laughter) That's hilarious.

RAE: And just - 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: Did your parents help you through that at all? Did they have any helpful advice or reassurance?

RAE: Well, my dad just being African was like deal with it, like, stop crying. And my mom, she tried to get it. But she was - her thing was just always about embracing it. And nobody wants to hear that. Like, no, I think being a teen and being a preteen is all about, like, fitting in and not standing out. And everything that she told me to do would be - would cause me to stand out, like embrace your hair and, you know, if they're talking about the way that you're talking, then just say I'm smart. That's why, you know? Or I'm speaking English correctly. And it's like, mom, no, nobody wants to - I'm not trying to feel superior. I just want - I want people to like me.

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? Because 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 were obstacles that black people faced. But in his mind, those are - 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.

BIANCULLI: Issa Rae, the star and co-creator of HBO's "Insecure," which returns for its second season this Sunday. She'll be back after a break. Also, we'll remember horror film director George Romero, who died last Sunday. And film critic David Edelstein reviews the new World War II movie "Dunkirk." I'm David Bianculli, and this is FRESH AIR.


BIANCULLI: This is FRESH AIR. I'm David Bianculli in for Terry Gross, back with more of Terry's interview from last year with Issa Rae. She's the co-creator and star of the HBO comedy series "Insecure," which begins its second season this Sunday. She also created and starred in the web comedy series "The Misadventures Of Awkward Black Girl," the same title she gave her memoir. When we left off, Issa Rae was talking about her father, who was born in Senegal, West Africa, before emigrating to America and working hard to build a successful life here.


GROSS: So you lived for I think two periods of your life in Senegal.

RAE: Just one period in my life.

GROSS: And the other time was just for a visit?

RAE: Visiting. So I used to go back, like, you know, every summer.

GROSS: So how did...

RAE: I'm overstating that, sorry. So I went back...

GROSS: Lots of summers (laughter).

RAE: Yes, lots of summers.

GROSS: So in terms of, like, fitting in versus feeling awkward, how did you register those feelings in Senegal? Where did you fit on the scale?

RAE: It's so interesting because my Americanness brought me some street cred in a way just because pop culturally - a lot of my cousins - I had a lot of cousins out there. And I remember going there for the summer, everyone would gather at, like, 4 o'clock to watch "Elech O'Malibu," (ph) which was like "Baywatch." And that was, like, the show to watch, and then "90210" would come on right afterwards.

And I remember them asking me like, wow, you're from LA. Do you see - like, do you see Donna? Do you see Dylan just on the street? And I'd be like yeah, I do. You know, I was just at Kelly's house last week. And they bought it. And that - like, my Americanness for the pop cultural side was valued in a way. It made me cool.

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. Were you considered more beautiful in Senegal than you were in LA?

RAE: Yeah. I think when you're in a country with people who look like you and have your features and who are married to people with their - your features and attracted to it, it just - 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?

RAE: Yeah, I mean, I was...

GROSS: You're sending in scripts.

RAE: 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, it felt like I wanted to be a part of the writers' 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 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 I - 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, 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 a 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 telling - 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 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.

RAE: Yeah. From babies, yeah.

GROSS: Did you ever get any encouraging notes in return?

RAE: The most encouraging note I got ever was when I saw "Love & Basketball" and fell in love with that movie. And that actually made me want to write films. And I remember writing my own script just because I loved that movie so much. And I reached out to Gina Prince-Bythewood. I don't know how I got her address, but I wrote her a letter and just told her how "Love & Basketball" inspired me, and I would really love for her to direct my script if she ever had the time, but just - either way, I loved her.

And three months passed, and I forgot that I wrote her a letter. But then I got an email from her that gave me all the props for writing a script at, you know, 16. And then she told me about the son that she was going to have and was, like, you know, unfortunately, I wouldn't be able to direct your script, but please keep doing it - and just was super encouraging. And I remember, you know, holding onto that letter - I still have it - and feeling super encouraged to continue.

And then she watched "Awkward Black Girl." She actually - we actually referenced the movie "Love & Basketball" in an episode of "Awkward Black Girl." So to know that she had seen it and given me props and encouraged me again was incredible. And then I showed her the letter that she sent me. I sent it back to her, and she was just amazed that I had it and that, you know - she was, like, thank God I wrote you back (laughter).

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.

BIANCULLI: Issa Rae speaking to Terry Gross last year. Her HBO comedy series, "Insecure," begins its second season on Sunday. Coming up, we remember horror film director George Romero, who died last Sunday, by listening back to an interview with him and another with Tom Savini, who worked with him as special effects director on one of Romero's most famous zombie films, "Dawn Of The Dead." This is FRESH AIR. Transcript provided by NPR, Copyright NPR.