Rebecca: I'm Rebecca Carroll, and this is Come Through. 15 essential conversations about race in a pivotal year for America.

Celebrities are a strange breed — a privileged tribe of attractive people, many of whom live and breathe rarified air, lounging around in big houses sifting through film scripts, project treatments or Late Night TV appearance requests. In America, we created this cult of celebrity as a way to worship that which we desired. And what America has always aspired in addition to wealth and success, is whiteness. 

In fact, when we talk about mainstream media, or mainstream popular culture, what and who we’re really talking about is white people. Black folks, despite our substantial, consistently game-changing contributions to music, film, art, sports, literature and American culture at large — have been relegated to “niche” markets throughout history, no matter how talented, known or productive we are.

But that has changed in recent years. Right now we are experiencing what a lot of black creatives consider a changing of the guard — an opportunity to level up in mainstream popular culture, and create great art, work and entertainment without the stamp of approval from white audiences, consumers, and executives. 

Writer, producer and actress Issa Rae is one member of that new guard.

Issa has had a hell of a glow-up over the past five years -- she’s probably best known for creating and starring in Insecure on HBO. And she thinks it’s time for black folks to pull each other up and into the rooms where we need to be so that we can make the decisions about what we see and how we are seen.

I’ve known Issa for nearly a decade. When I met her, she had just launched The Misadventures of Awkward Black Girl, a web series, which, pretty much as it sounds, follows the very often uncomfortable adventures of a 20-something black woman just trying to live her life. Even though all the black folks that I knew were obsessed with the series — Issa wasn’t making any money from it. She had a day job but was still broke, and, she told me back then, she sometimes felt like giving up.

Well, she clearly did not give up. Awkward Black Girl became a runaway hit, and caught the attention of writer and producer Larry Wilmore, who helped her negotiate a TV deal with an early iteration of Insecure. But it took years for that to happen. And when it did, things got very real. 

In the past two years alone, Issa has landed starring roles in three feature films, and has appeared on multiple magazine covers. She’s a full-blown celebrity now, and she’s still black as hell. And that is interesting to me. Because yes, black folks tend to stay real black, and we maybe even get a bit blacker during times of crisis — we rely on the faith, resilience, collective joy and strength that has kept us here and whole in America.

But I’ve watched Issa’s entire aesthetic change from a bit scrappy and very awkward - to celebrity chic, fashion-focused and super poised. Not that doing any or all of these things makes her less black. But I’ve been fascinated by how Issa navigates mainstream celebrity as a black woman, how she stays true to her vision, and maintains her sense of autonomy.

I talked to Issa a couple days before the new season of Insecure dropped — Twitter was absolutely abuzz. And I asked her -how’s that feel?

 

Issa: Flattering and horrifying because that comes with a lot of expectations. People are literally like, - Oh, do you feel a lot of pressure when you're coming back? Because you took some time off? And you know, before it was like, no. I mean, I'm excited that people want to see it, and it'll come and then it'll go like it always does. And now it just feels like. So many eyes are on it. And the anticipation, I hate anticipation. I hate hype. I try to under hype as much as possible. I'm excited that people feel like it'll be their escape. And you know, with some people who I've talked to who have seen the first five have said, you know, it feels like I am with my friends again, or I have my old friends back. And that makes me feel really good. That people identify with the characters in that way. So, I'm happy and scared. Well,

Rebecca: Wait, you said you hate hype? Are you superstitious person? Is that why?

Issa: Oh, yes. I am very superstitious. I blame my family. I am. I hate the idea of jinxing things. Like, I won't say things out loud. I won't say what I'm working on because it'll go away. And that happens. Every time I fight - I'm like, don't say anything. Don't say anything to your friend. Because as soon as you say it, you know it's not gonna happen anymore. And every time I say it, it disappears. So yes, I'm very superstitious in that way.

Rebecca: I want to revisit that a little bit later, but first lets just sort of in terms of how we know each other. We first met about 10 years ago?

Issa: Back in the day!

Rebecca: yeah, yeah.

And that was when Awkward Black Girl was really just starting to take off. Every black person I knew was obsessed with it. But you weren't actually making any money off of it at the time?

Issa: No, I still had a job when I met you.

Rebecca: What was that job?

Issa: I was working for the March of Dimes at the time.

Rebecca: Oh, I'm starting to see. Was that an inspiration for...?

Issa: Yes it was. It was one of them.

I had a couple of nonprofit jobs, but yes, that was, that definitely inspired, Insecure.

I think nonprofit environments are kind of competitive in a way for where altruism is concerned. And I always found that very interesting and comical, and I just always felt like I wasn't doing enough, or maybe I didn't. Care enough and how that was reflected and yeah, it was just an interesting group of people.

Rebecca: And, so back in your Awkward Black Girl days, you were operating with a pretty bare bones team, right. Which was probably both fun and exhausting. Was there a moment when you were like, this just isn't worth it?

Issa: Heck yeah. I mean, the first one happened When I just didn't have any more money, uh, season one. Um, but then when we were able to raise funding during that Kickstarter, it was great. It reinvigorated it more people found out about it. And then season two was just really hard for a lot of different reasons.

People don't realize that, like the actors in the show were friends of mine who have real jobs. Some of them were working in San Francisco. Some of them were, you know, living abroad. So it was always hard to get people together on a schedule. And yeah, I kind of couldn't wait to be done with it. It was, it was very eye opening to what the industry could be like.

And I think that that ended up being a bootcamp and helping me to kind of just do better when I finally got the opportunity to have a show. You know, I learned a lot of lessons from working on that show.

 

Rebecca: And then, a few years after we first met, we had this conversation that I often revisit in my mind. We were at South by Southwest having dinner with a bunch of folks. And we were all talking about the various side hustles and ways that we're trying to live and survive - like, oh maybe I’ll start a blog, or maybe I’ll start a youtube channel, but you were like - that’s not for me, I have a vision and I’m gonna stay in my lane. Do you remember that conversation?

 

Issa: Mm. I mean, that feels so interesting. I like, I still feel that way, but I've obviously dabbled in a lot of lanes now. I would still maintain that. I say, I know what I'm not going to do. Like, I know that I'm not really passionate about directing and don't feel the need to be a director just because women aren't as prominent, and you know - black women especially aren’t as prominent.

And so I'm just like, Oh, I don't like to do that. And so I can, you know, work with, or hire people that do. And there are other business ideas, and other ventures and things, that I'm just not interested in. I'm blessed to be able to say that I pursue things that I'm interested in.

Rebecca: So, how did you find your lane and how have you stayed in it at the end of the day?

Issa: I found my lane by just being true to myself. Like it's always been driven by a passion for what I like, what I want to see. What I feel like I could bring to the table. And I don't like to feel like I'm in a crowded space by any means. Cause then I'm just like, well, what's the use for me? What can I contribute that a hundred other people aren't?

And. Again, that's ironic for television because it is such a crowded space, but I think for me, it's just about finding these niche stories, and very specific stories in anything that I do. Whether that's podcasting or music or whatever. I think that I'm always asking myself the question, what can I do that's different?

Rebecca: Yeah. I mean, it's funny and also interesting that you mentioned niche stories. Because in so many ways they, they aren't niche. I mean, you have sort of created stories in a way that speaks to such a broader audience, right? I think about The Photograph. That movie is actually. I mean from the outset, maybe niche, but the actual story and the relationships and the themes are not.  And so I think it's interesting to kind of grapple with the idea of what niche means, particularly at the intersection of race.

Issa: That's actually a great point. And I think that that, that's also always bothered me in the description of it, but I think where my stories are concerned - specifically, it's because I thought of them as smaller stories. You know, stories about my friends, my family, you know, I think those don't feel like they're necessarily universal stock topics.

I think something like Awkward Black Girl felt also niche because of the specificity in the title. But I knew that the awkwardness was a universal experience. It was more about how I related to the black experience.

Rebecca: You've had a pretty extraordinary glow up, I would say in the time since we've met.

Right? I mean, you've had starring roles in three major motion picture movies in less than two years. That's wild. And you're producing all sorts of other materials and multiple magazine covers, girl, multiple. Are you past the novelty of it? What does it feel like to have arrived. 

Issa: To have arrived. I'm definitely not past the novelty of it. Because it just feels like -  it still feels like I have a lot to prove.

I do have a lot to prove. Especially in this starring role lane. Like, cause I've never considered myself an actress first. I've always considered myself a writer, a producer first. And so. If I'm going to keep taking these opportunities, I want to Excel. And so in that way, it still feels novel, it still feels exciting and a little bit scary. And I, I joke that, and it's not necessarily a joke, but I think about how I started. I started with a sense of confidence. Because it was just like, I'm creating this archetype, I'm creating these characters, and, producing for the internet and making something from scratch and forging a career for myself.

And now that I'm in it, there's a sense of insecurity that comes with -Oh, well how long do I have here, and what more can I do that will be accepted? You know, what will be my legacy? I don't want to be a flash in the pan moment. And you know, am I good enough to stay?

That’s Issa Rae - coming up - the value of Black cultural criticism... and it’s limits.

Hey everyone! Before we get back to Issa, I just wanted to take a quick second and say THANK YOU for listening to this show and for the boost you’ve given it these last couple weeks. This pandemic has been so isolating for us all… and it’s been extra inspiring to hear from you and connect with you on Twitter.

And I want to say a special thank you to the people who have reviewed the show on Apple Podcasts. It’s a huge help to us, getting the word out about this show. AND it lets us know where you’re at, what you’re thinking, where you are in this conversation we’re having.

So please keep reaching out. Review the show. And find me on Twitter, I’m @rebel19.

Thanks again and now, back to Issa.

Rebecca: What is the difference for you between a cover on Teen Vogue and a cover on Essence?

Issa: The cover on Essence means more, and it also looks better, to be honest.

The cover on the Essence, I've always valued the love and support of us more than anything. Like to me, it almost hurts when you're valued by others more than us, you know? And I think, I don't want that, you know? And for me, the support, and appreciation, and love from a publication like Essence, and I think just black people in general. That's a milestone for me. And that's what keeps me going.

Rebecca: That's an amazing thing that you said right there of, it almost hurts to be valued more by others. And by others, I presume you mean white folks. Which definitely speaks directly into, you know, this book that I've written called Surviving the White Gaze. But that the white gaze, that we give so much power to, it does hurt.

It's like Tony Morrison’s The Bluest Eye. It's like, how do we get out from under that? And it sounds to me like you were never under it to begin with.

Issa: But I, I was, I think, I think there's still a validation that comes from, the approval of white publications and white media.

Like all of that is still necessary for visibility. And so in that way, absolutely. And, you know, I'm still on a white network. You know, I think for me it's just as long as I'm staying true to myself and who I'm making the content for - it might not matter what medium. I don't want this to be a permanent thing for me.

But yeah, I think in some ways when you get those reviews from white publications and ultimately white critics that are approving of your work, that helps. And it's sucks. But I think, you know, now there's a great conversation happening around black critics, and the value of their voices when it comes to works of color. And all work in general.

Rebecca: What does it feel like? I wonder when there is sort of pointed criticism from a black critic about something you've done.

Issa:  It depends on who the black critic is. Because I can be 100% honest and say that there are some that I just know don't fuck with me. And so, I don't really respect their opinions. And I almost get frustrated, like, without calling one out, there's one I'm like - why does this bitch have a business writing about the show when  it's clear that she doesn't fuck with me?

But then the other ones where when they're, the critique is. It's a critique is valid. And if I, whether I agree with it or not, I respect their opinions. I'm like, Oh, I read their work independent of my own and really respect what they have to say. So if they didn't fuck with this episode, they didn't get it. Okay. There's validity there and I'm fine with that.

I can sleep at night, but I just ask for thoughtful responses and I ask that you not be harder on the work of black people. Cause I feel like I see that often too. Where you have to prove that you're being fair,  so you hyper critique the works of black artists.

And I see that a lot too in some of my peers work. And I'm just like, is this coming from a sincere place, or is this coming from a snarky place of posturing? So there's a balance

Rebecca:  No, I was just going to say, I was drinking from my, "I'm rooting for everybody black" mug this morning. Which is a direct quote from you, of course, and thinking about like, I am rooting for everybody black. And so, it is a little bit tricky. This whole kind of criticism and this conversation around black critics that has really blossomed and I think is very healthy in some ways, but it's also, it's like, it's us.

Issa: It is. It's us. All we have, and we're ones that are going to ultimately be honest with each other. And we're the ones who the work is going to live through. We're the ones who, you know, maintain the memories of our work ,and the importance of it. And so, yeah, it's important. So

Rebecca: Yeah. so for this podcast, we're asking folks to have essential conversations about this year, which is already just banana pants. Um, what, what do you think are the essential conversations we should be having?

Issa: In general?  How we care for the elderly in this country that’s been plaguing me. Just, from personal experience, and what I've observed. And how we tend to people who don't have the means to take care of themselves.

I think that those are essential conversations that we need to have. Especially, as we're realizing and seeing that this virus is affecting us. And you know, in some cases I'm not even a conspiracy theorist, but I know when the decision has to be made to resuscitate or give us the best care that we're not always a priority.

And some part of me is just like - you know, hearing that it’s affecting black people the most will make things more lax in a way. And that deeply concerns me.

Rebecca: Yeah, me too. But how about in terms of creativity? What's the essential conversation around that this year?

The conversations about the ownership and the, the restructuring of this industry.

I think we're at a pivotal time. Given that we're at a stop and we're seeing how much entertainment is valued and what kind of entertainment is valued to really put our entertainment, in particular on a pedestal and make sure that it gets the respect that it deserves and in a more structured way and in an organized way.

I'm not sure what that looks like, but those are the conversations that I'm interested in having.

Rebecca:  And so, given that we've discussed the power and importance of, not necessarily approval, but I guess a stamp of approval from white audiences. Do you feel like we're, we're going to be able as black folks to take this moment and really leverage our skills and our creativity and find our way out of this, this moment?

Issa: I think we always do. So, I think this time will be no different. And I'm very confident in the people who are players. And I'm also confident in everybody who has a part in this industry right now, and. I think the conversations are so public and the knowledge is just getting more centralized in a way - that I think, yes, absolutely. I think this is the time. This feels like a revolutionary time in that way.

Rebecca: And so what are you hearing and what kinds of conversations are you having with your folks, with your people, with your community and the industry?

Issa: The last conversation I had that was interesting was actually with Justin Simien who I love. And we were just talking about how things have evolved and how, in a sense, we started off watching very limited black creators coming up. And either being inspired by them or feeling like we were being let down by them. And it's interesting to be in a position where now we're subject to the same criticism or inspiration. And I think, to the earlier point of, like what we're doing with it. What is our moment? Will it last long? Will it not? And what are we creating and how are we helping the next generation of creators to find a place within this industry?

And I think, that's definitely a priority for so many of us who are here. It's just like we have the door open, so how can we push as many people through as possible - in addition to trying to train the, the next pool of executives that will be the decision makers. And how do we just create a stake, a long-lasting stake in this industry so that we're not constantly having the same conversations about black waves of content, and, Oh, how great this Renaissance is. You know? Um, so that's a huge part of the conversations that we're having.

It's about creating things that we can ultimately own.

Rebecca: It's striking to me, you know, the old saying, America gets a cold and black folks get pneumonia. But I also think, you know, reflecting on what you just said, which is that we always do come out of this. And I guess I would love to hear from you what on a daily basis do you turn to, to reassure yourself of that?

Issa: Um, I mean, outside of my family, and my mother - I turned to the people that I work with, which I consider my creative community. Oddly enough, I read a lot of voices on Twitter, even though I've been staying away from Twitter a lot for the last couple of years. And trying to take breaks and things like that, but I found myself going there more just to know how people are feeling, what they're going through, just to get a handle on the community sentiment.

And for me that's reassuring cause it points out a lot of problems to me. It just feels real and of course it always feels amplified, which is my problem with that medium to begin with, but that's kind of my comfort place right now, in the panic. And journalists. Good journalists for sure are keeping me hopeful, keeping me in the know, and just keeping me inspired in new ways. When they're not, you know, causing me extreme anxiety.

Rebecca: What's something trashy you're doing to cope? For me, it’s White Cheddar Cheez-its. Like, three or four bowls at a time. It's like, I don't even know why. Like what is that?

Issa: It's the right thing to indulge cause I'm doing the same thing. Like I have been on, I'm like when I get out of this pandemic, and I get to go into the sun, I want a bikini body. And so I've been eating really well and you know, doing my little workouts.

I understand that like why prisoners get so buff cause they don't have shit to do. But at the same time I have like a separate Finsta that only follows food accounts. And there's this. This account that I followed for like a year now called World's Best Cookie Dough. And they always have the most delicious looking fucking cookies and cookie dough batter ever.

And I never ordered it cause I'm always on, you know, trying to be good. So I'm like, let me not put it in my house. But it came and I had been fucking these cookies up like in every which way. So, I will do the same as you - where I cook and really admirable meal and then just fuck that cookie dough up.

Rebecca: I love it. I love it. All right. Keep doing you and thank you so much.

Issa: Thank you so much, and congratulations! I hope our paths cross again soon.

That’s Issa Rae. You can watch Season 4 of Insecure now on HBO.

Come Through is a production of WNYC Studios.

Christina Djossa and Joanna Solotaroff produce the show, with editing by Anna Holmes and Jenny Lawton. Our technical director is Joe Plourde, and the music is by Isaac Jones. Special thanks to Anthony Bansie.

And I want to give a very special shout-out to Paula Szuchman - our executive producer. Paula’s moving on to a very exciting position at the New York Times - I cannot wait to listen to what she makes. Paula championed this show from the very beginning and helped us make it what it is - Paula we could not have done this without you.

Again, you can follow me @Rebel19 for all things Come Through - and - if you liked the show, please rate and review us. Until next time.