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

TERRY GROSS, HOST:

This is FRESH AIR. I'm Terry Gross. You can get a sense of my guest Issa Rae's self-image by the titles of her best-known works. Her new HBO series is called "Insecure." The web comedy series and memoir that preceded it were both titled "The Misadventures Of Awkward Black Girl."

They're all about issues of identity and feelings of not fitting in, things Issa Rae dealt with all the time 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. She's also lived in Senegal, where her father is from, where she was the only American in her 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. She lives with her boyfriend but isn't sure the relationship has a future, and her job isn't fulfilling her creative impulses. She works as the youth liaison at a nonprofit called We Got Y'all, which works with predominantly African-American schools, offering students mentoring programs, afterschool tutoring, standardized test coaching and other things to try to supplement what the students haven't been getting in school.

Here's a scene from episode one, in which she's talking to a class of junior-high students.

(SOUNDBITE OF TV SHOW, "INSECURE")

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?

(LAUGHTER)

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.

(LAUGHTER)

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

LISA JOYCE: (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 interests 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.

(LAUGHTER)

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'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)

IVAN 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.

(LAUGHTER)

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 non-profit 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: 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? 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: I 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.

(LAUGHTER)

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 I - even in my adult life, like, if I see a group of kids, you know, having a conversation, having a good time, I will cross the street 'cause, like, at that time, they are so - they're just so mean and so funny at the same time. Like, I think about so many of the things that kids made fun of me for and the insults they had. 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 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 the scene ends, but it starts with a voiceover.

(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, that's what we're talking about?

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 '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). 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: So there's a lot of code switching that happens in "Insecure." And your character even is practicing different ways of speaking and being in rehearsing options that she can say to her ex-boyfriend when she meets him for the first time in several years. And she's in front of the mirror putting on different shades of lipstick. And with each shade of lipstick she puts on, she talks differently. And then after doing this for a long time, she finally just puts on lip balm. (Laughter) And to me, the lip balm means, like - not, like, I am proud of who I am and I'm just going to be myself. It's more like, ugh, I'm resigned to who I am...

RAE: Yeah.

GROSS: ...And I have no choice but to be myself (laughter).

RAE: Yep, that's it. It's the easiest to be myself at this point.

GROSS: (Laughter) So can you talk about some of the different ways of speaking that your character is trying on to rehearse approaching her ex-boyfriend?

RAE: Well, in that particular scene, she wants - she's already made a declaration that she wants to be kind of - she wants to go after what she wants. And these lipsticks allow her to try on literally different personalities and to try to be the fun one, the aggressive one, the exotic, you know, dainty one. And, you know, at the end of the day, she realizes, OK, I'm not good at being any of these people. And I just might as well be myself. And she does - she has a lot of those moments in the bathroom in particular. I think the bathroom is definitely her safe space and this space where she can actually be vulnerable and express herself in an extremely honest way. It's the only place that she is actually honest with herself and expresses her thoughts in a way that she can't in the outside world because she's a self-described aggressively-passive person. So you'll see a lot of those mirror moments where she's kind of forced to face her truth and herself at the end of the day.

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.

(SOUNDBITE OF MUSIC)

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 move 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.

RAE: 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: So there's a lot of code switching that happens in "Insecure." And your character even is practicing different ways of speaking and being in rehearsing options that she can say to her ex-boyfriend when she meets him for the first time in several years. And she's in front of the mirror putting on different shades of lipstick. And with each shade of lipstick she puts on, she talks differently. And then after doing this for a long time, she finally just puts on lip balm. (Laughter) And to me, the lip balm means, like - not, like, I am proud of who I am and I'm just going to be myself. It's more like, ugh, I'm resigned to who I am...

RAE: Yeah.

GROSS: ...And I have no choice but to be myself (laughter).

RAE: Yep, that's it. It's the easiest to be myself at this point.

GROSS: (Laughter) So can you talk about some of the different ways of speaking that your character is trying on to rehearse approaching her ex-boyfriend?

RAE: Well, in that particular scene, she wants - she's already made a declaration that she wants to be kind of - she wants to go after what she wants. And these lipsticks allow her to try on literally different personalities and to try to be the fun one, the aggressive one, the exotic, you know, dainty one. And, you know, at the end of the day, she realizes, OK, I'm not good at being any of these people. And I just might as well be myself. And she does - she has a lot of those moments in the bathroom in particular. I think the bathroom is definitely her safe space and this space where she can actually be vulnerable and express herself in an extremely honest way. It's the only place that she is actually honest with herself and expresses her thoughts in a way that she can't in the outside world because she's a self-described aggressively-passive person. So you'll see a lot of those mirror moments where she's kind of forced to face her truth and herself at the end of the day.

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.

(SOUNDBITE OF MUSIC)

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 move 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...

(LAUGHTER)

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 friend's 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: My guest is Issa Rae. Her comedy series "Insecure" premiered on HBO a few weeks ago. We'll talk more after a break. And John Powers will review the new film "Certain Women," starring Laura Dern, Kristen Stewart and Michelle Williams. I'm Terry Gross, and this is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. I'm Terry Gross, back with Issa Rae, the co-creator and star of the HBO comedy series "Insecure," which premiered on HBO a few weeks ago. Before that, she 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, we were talking about her childhood. She was one of the few black students in her elementary school in Potomac, Md. When she moved to LA, she went to a predominantly black junior high. She says it was a bit of a culture shock.

RAE: It was just because I was watching a lot of television, and so I watch shows like "Saved By The Bell." Even though that wasn't set in LA, I just thought that would be my LA experience. And "90201..."

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 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.

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...

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. Now, 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 or 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: When you were getting started and starting to get serious about, you know, writing and acting, your apartment was broken into and your laptops, your videos, your cameras, all your work was basically stolen. You hadn't backed up (laughter) shame on you. Did you interpret a hidden message with that, like the gods were telling you just, like, give up or that the gods were telling you start a different project or - you know what I mean? Sometimes something happens...

RAE: Yes.

GROSS: ...To you and you figure, like, there's a secret message here. What does it mean?

RAE: That's such a good point, actually. So I was in New York when that happened, and I was struggling. And, well, the start a different project aspect that you just said is so interesting just because that's the advice that I always give to up-and-coming creators because I have seen people constantly try to peddle the same project over the course of years. And it's like you should have multiple projects going on. And I think I was in a state where I was trying to peddle the same project and trying to get it to television. And I actually - the day after the robbery, I was supposed to have a meeting. Like, the day before I was supposed to have this major meeting to try to take this project to television is when my apartment got robbed. And I lost all of the materials that I didn't back up. Thanks, Terry.

But that was a great - for me, a great sign that one, I shouldn't be in New York. Like, I was willingly struggling, and I stayed there an extra year after that despite knowing that and that I needed to try other projects. And that next year is when I came up with the idea for "Awkward Black Girl" but didn't necessarily pursue it because I felt like I was - I was too broke but just started writing more and also just - that next year I also decided to move back to LA, where I knew people and I had more resources and could rely on people to actually help me get my projects done.

GROSS: So your first series, "Awkward Black Girl," was a web series. And it was a very successful web series. What was your approach to getting some attention, to getting noticed? The web has, like, so much stuff on it. Anyone could put anything on there, but it takes a lot to have somebody else notice that it's there.

RAE: Yeah. Well, by the time I did "Awkward Black Girl," it was my third go-around. I was actively producing another web series that - about my brother's group, my brother's music group trying to make it in LA. And it was the first time that I had started to take web series seriously in that I was producing an episode - every Monday at 10 a.m., you could expect a new episode. And, you know, I would put off social plans to be like no, I have to edit this and no, I have to write the outline for the episode and then shoot it and, you know, putting in work just so that we could build an audience. And I realized then - I was like man, it's just not doing the numbers that I want, and I feel like they're so talented and it's really good. And what is the issue? Each episode was seven minutes, and that could have been part of our problem during that time.

So by the time I did "Awkward Black Girl," I was like I'm going to learn from all the mistakes of my other two web series. For one, I know the first episode won't be longer than three or four minutes because people don't have attention spans. Also, I'm just going to write what's close to me and what I know and really tap into my network, which is not to say I wasn't doing that for the other web series, but I really just put it out there to my family and friends and made it for my family and friends and just published it to Facebook, went to sleep. And by the time I woke up, it had really spread amongst my social network, and people were spreading the word on their own in a way that they weren't or they hadn't done for my previous web series.

GROSS: So how'd you go from YouTube to HBO? It's a big jump.

RAE: Oh, that was a journey as well. You know, I - our second season of "Awkward Black Girl" was produced by Pharrell Williams via his i am OTHER company. And that got press, and we got reviewed in The New York Times for our second-season opening. And that got the attention of ABC and ShondaLand. And I got an opportunity to develop a pilot with them, a completely different pilot called "I Hate L.A. Dudes."

And ABC ended up passing on that project, and, you know, I was devastated. I was like man, I blew my one shot. And then HBO called me and said, hey, we heard that you're free - you know, not a month later or two months later, they said, hey, we hear that you're free. Do you have any ideas to pitch for us? And then I pitched them the idea that ultimately became "Insecure."

GROSS: If you're just joining us, my guest is Issa Rae. She is the creator and star of the HBO series "Insecure." And before that, she did the web series "Awkward Black Girl." We're going to take a short break here, then we'll be right back. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

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 "Awkward Black Girl." 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 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: 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 "Awkward Black Girl." So were you brought up with traditions, cultural or religious, from either of your parents?

RAE: Well, my mom is a Christian, and so she raised us as Christians. And so - I mean, that was the - that was pretty much the extent of it. I think when I went back to Senegal for certain summers, if Ramadan would fall during the summer, or Tabaski, which is like the celebration after Ramadan where they kill a goat to celebrate, that is the closest. But for the most part, I've really just tried to form my own opinions and forge my own relationship with spirituality.

GROSS: So since your father was brought up in the Muslim tradition, in the Muslim faith, what's it been like for you to watch his faith be demonized by parts of America?

RAE: Well, for me, it's just always been puzzling just because I've - you know, half of my family is Muslim. So I - the picture that's being painted is of an extreme, you know, facet of Islam. And that's like really - that's like holding Christianity accountable for the actions of the KKK, you know? It's just - it's always been absurd to me. And I've seen - you know, and obviously I have Muslim friends too who just hate that the reputation of Islam is being held by this small group of violent people. It's absolutely unfair. And, you know, I've seen him get upset over it, and lots of my family members rebuke the actions of these terrorists at the end of the day. But that shouldn't be - it just has never made sense to me that people will take a small group of people and judge an entire group.

GROSS: So I listen to a lot of voices (laughter) in hosting this show. And I love your voice. You have a beautiful voice.

RAE: What?

GROSS: It's sort of, like, deep and resonant and...

RAE: (Laughter) Thank you.

GROSS: So when you were - how old were you when it started to get that kind of, you know, depth, that resonance?

RAE: Jeez.

GROSS: You didn't have that in high school, did you?

RAE: 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, 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: (Laughter).

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 because you're not. And I'm, like, because 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 is the co-creator and star of the HBO comedy series "Insecure." Episode six will be shown this Sunday. Coming up, John Powers reviews the film "Certain Women," directed by Kelly Reichardt, starring Laura Dern, Kristen Stewart and Michelle Williams. That's after a break. This is FRESH AIR.

TERRY GROSS, HOST:

This is FRESH AIR. Filmmaker Kelly Reichardt has been described in The New York Times as making feminist Westerns. In her new film "Certain Women," she looks at the intersecting lives of several Montana women played by Laura Dern, Michelle Williams, Kristen Stewart and Lily Gladstone. Our critic-at-large John Powers has this review.

JOHN POWERS, BYLINE: I once took a trip up the Amazon, and the boat went so slowly that for the first several hours all I noticed was my own boredom. But gradually, my inner clock began slowing down. And as I gave myself over to river time, I began to take in the wonders around me. I saw pink freshwater dolphins leaping out of the corner of my eye.

You might find yourself having a similar experience watching the films of Kelly Reichardt, whose almost saintly integrity has won her worldwide critical acclaim but left her largely unknown to the public. Ever since her 1994 debut "River Of Grass," this 52-year-old filmmaker has developed a stripped-down vision uniquely her own, one that asks you to give yourself over to her quiet restraint and unhurried rhythm.

Her latest film, "Certain Women," is one of her finest. Based on short stories by Maile Meloy, it tells the loosely interlinked tales of three women in small-town Montana, where the air is chill and the skies are gray. In the first, the great Laura Dern plays a lawyer with a slippery boyfriend. She's having trouble with a blue-collar client - that's Jared Harris - who wants something more heartfelt from her than legal advice.

In the second, Michelle Williams shines as a does-everything wife with a slippery husband and a sulky daughter, who focuses her bristling energy onto getting authentic local sandstone for a new house. These rather wispy stories set us up for the third and richest one, which centers on a moving turn by newcomer Lily Gladstone. She plays a lonely Native American ranch hand who stumbles across a night class taught by a badly-dressed young lawyer, Beth Travis, superbly played by Kristen Stewart, who must drive four hours each way to teach it.

Quickly developing a crush, she takes Beth to the local diner. And these two awkward women develop a bond whose fragility will become agonizing to watch. Here, she asks Stewart's lawyer why she once mentioned she feared that she might wind up selling shoes.

(SOUNDBITE OF FILM, "CERTAIN WOMEN")

LILY GLADSTONE: (As Jamie) Why were you afraid of selling shoes?

KRISTEN STEWART: (As Elizabeth Travis) Have you ever sold shoes?

GLADSTONE: (As Jamie) I mean, why were you afraid you couldn't get anything else?

STEWART: (As Elizabeth Travis) I don't know, because my mom works in a school cafeteria, my sister in a hospital laundry. So selling shoes is the nicest job a girl from my family's supposed to get.

POWERS: Now, in some ways, Reichardt's work is most startling for what it refuses to be. Where Hollywood likes big, easy-to-market storylines, her films are almost like haikus - two friends take a seemingly uneventful camping trip in "Old Joy," a drifter searches for her missing dog in "Wendy And Lucy." Where Hollywood heroes are larger than life, Reichardt's live marginal existences, either psychologically or materially, and often have no clear idea what to do. Where Hollywood specializes in punchy dialogue, her characters are so laconic or inarticulate that they make the yup-nope cowboys of yore seem positively garrulous.

And have I mentioned that she's fascinated by female stoicism? In fact, Reichardt is tuned to precisely the thing that most movies cut out, the largely undramatic texture of daily life. She pays rapt attention to silences. She lingers over small private moments charged with ambivalence yearning or fleeting joy and she captures how her characters fit into the vast, sometimes overwhelming landscape of the American frontier, as in her feminist Western "Meek's Cutoff," the most realistic film I've ever seen about the crushing rigors of crossing America in a wagon train.

You find all of this and more in "Certain Women," whose heroines, all tremendously well-acted, are marked by their bottled-up uncertainty. Should Dern's goodhearted lawyer be warmer to her troubled client, even though he doesn't trust her legal advice because she's a woman? Will Williams's wife really find satisfaction when she finally gets that sandstone, or is she actually building herself a prison? And what does the yearning bighearted ranch hand learn from an affection for Beth that she knows is impossible?

These are the kinds of questions that can't be answered by the usual movie methods - cape crusaders, psycho-drama showdowns, miraculous plot twists. They must be approached with the same patience and care that Reichardt brings to her filmmaking. Her movies are all about noticing small things to discover the enormous things within. This doesn't happen quickly. But like life itself, her work has a way of sneaking up on you.

GROSS: John Powers is film and TV critic for Vogue and vogue.com.

(SOUNDBITE OF MUSIC)

GROSS: Tomorrow on FRESH AIR, my guest will be James Fallows, who has been writing an election blog for The Atlantic. He's the magazine's national correspondent. Earlier this year, he wrote an article called "How America Is Putting Itself Back Together" based on three years of flying around the country in a single-engine plane. I hope you'll join us.

FRESH AIR's executive producer is Danny Miller. Our interviews and reviews are produced and edited by Amy Salit, Phyllis Myers, Ann Marie Baldonado, Sam Briger, Lauren Krenzel, John Sheehan, Heidi Saman, Therese Madden and Mooj Zadie. I'm Terry Gross.

Transcripts are created on a rush deadline, and accuracy and availability may vary. This text may not be in its final form and may be updated or revised in the future. Please be aware that the authoritative record of Fresh Air interviews and reviews are the audio recordings of each segment.