Issa Rae Talks 'Insecure' Season 2, Old TV Execs Dying Off, and Progress in Film and TV

Issa Rae is back for a new season of 'Insecure,' and sitting down with Nadeska Alexis for her first Complex Cover she talks the industry and life goals.

View this video on YouTube

Payback comes in many forms. Sometimes it's financial—cash, or something close to liquid. Other times it's an act of righteous revenge. Or it can be both, simultaneously: "Best revenge is your paper." Issa Rae paid her dues, working her way from a YouTube webseries called The Misadventures of Awkward Black Girl to a successful show with HBO, Insecure, and roles in upcoming feature films. She's getting her piece of the American pie after years of struggling to find the proper support for her creative vision. (The years-long journey from YouTube to a scrapped project with ABC to HBO was anything but smooth.) Now that she's here, she's making sure to give opportunities to other women and people of color—opportunities that otherwise wouldn't have been available without someone on the inside pushing for them.

Born in Los Angeles 32 years ago, Rae came of age in the city's Windsor Hills neighborhood, where Insecure often shoots. The show follows Issa, played by Rae, as she navigates an unfulfilling nonprofit education job and a complicated relationship with her long-time boyfriend (and now ex) Lawrence, played by Jay Ellis. Equally rich and intricate is her friendship with Molly, played by Yvonne Orji, who is a successful lawyer. It's a 30-minute, slice-of-life comedy with a killer soundtrack, a sincere appreciation for rap, and lived-in contemporary detail.

Speaking with Complex in 2016, Rae made it clear what Insecure is not. "I don’t want people to watch this show and assume this is the black female experience," she said. "It’s not. There will be stuff that any black woman who watches the show can relate to and there will be stuff where they’re like, 'Oh, that’s not me.' The most important thing is telling a very specific, authentic story, not trying to answer for all black people."

As it returns for its second season on July 23, in a Sunday night lineup that includes HBO's most watched show, Game of Thrones, Insecure will likely find an even bigger audience for the specific, authentic story of its multifaceted characters. But for her first appearance on the Complex Cover, the stage is Issa's.

This interview has been edited for clarity and length


A lot of people became familiar with the genius of Issa Rae when you debuted The Misadventures of Awkward Black Girl, but now you're about to release Season 2 of Insecure on HBO, which is amazing, so there's an entire generation of girls who are going to grow up watching you show them more dynamic images of black women and women of color on TV, which is incredible. What women did you grow up watching on TV that shaped the way you grew up?
I grew up watching Vanessa and Rudy on The Cosby Show. I grew up watching Laura on Family Matters. Moesha—Brandy as Moesha. I mean, Gina Prince-Bythewood, I always say inspired me, just viaLove & Basketball.

And Girlfriends, I know you're also, you're definitely a big, a big fan of.
Girlfriends huge—love Mara and what she did, and just the entire cast. I had a lot of black women to aspire to. Just in my childhood, to be like, "Oh, I want to be like her, look like her.” In music and in television.

And now you're that person for a whole generation, which is pretty amazing.
I don't think about that, but that's crazy. If that's the case I feel sorry for them.

Well, you're not supposed to think about it. You're supposed to keep working. HBO seems like they were really into the idea of you and your best friend Molly being the lead characters and following that friendship. How do we see that friendship develop in Season 2?
So, the friendship between Molly, what I love about it is that they tend to call each other on their shit, sometimes when it's necessary, sometimes they wait a little too late, but they'll do it nonetheless, and they do it to make each other better. So this season you'll see them kind of  calling each other to the carpet in terms of being honest with each other because last season they let a lot of stuff build, so when we come in this season they're like, "Look, we're being honest with each other. We have a trigger word that is to make sure that we're honest at all times," and so we're gonna see how that plays out throughout the season.

Have you enjoyed writing that story line? Does it reflect your real-life friendships?
So much. I love writing any Issa and Molly scenes. I love that they're there for each other and their friendship is real. It's not all flowers and roses. Like they're not out to get each other. they're not conniving and out to steal each other's men. They love each other genuinely. It's like a friendship—I mean it's a sisterhood, if anything. Yeah, that definitely reflects my own personal friendships. My friends are like some of my sisters. We know each other in and out and we also know each other's flaws and we'll call them out or work around them, but you know, we love each other flaws and all.

I think one of the most powerful things about the show that you said is that you're not trying to tell the story of every black woman, right? That would be completely ridiculous.
Mmhmm. Impossible.

Exactly. You're telling the story of these characters, but I think it's also cool that you've tried to hire a lot of staff of color to work behind the scenes.

Melina Matsoukas: We know her for directing incredible music videos for Beyoncé and Rihanna, but I think her first time directing for TV was working on your show. It seems like you guys have developed such a tight relationship and I'm curious how that synergy bleeds over into the show.
I’m so glad that they allowed us to take a risk with her because she’s just killed it. Even when she came in for the interview, we were all speaking the same language, me Prentice, and her, just like three black people talking about the black cultural elements that we wanted to include in the show without having to explain. Just knowing, like, “Oh, you get it.” When the biggest battle is I want to make this more basic and you want to make it more elevated, I say we have a great relationship. When she got the job we went to Matsuhisa, which is her favorite bougie sushi spot. We’re drinking and just getting to know each other, and since then we have developed a friendship where we kind of call each other out, just in terms of trying to make the best show possible. She may feel attacked like, “I feel like your wardrobe is too basic. Just give me some product. Give me some whatever," designers that I don't know. But I just love what she brings to the table, because she has an eye that none of us have, and just really brings a unique, special quality to the show.

You've explained that it was not easy hiring the people that you wanted for the show. The studio would always say they don't have enough experience, et cetera, but after she worked on Insecure, she's now directing episodes of Master of None. It's like your vision is unfolding pretty quickly.
It's amazing. It's just, like, you give someone an opportunity and if they knock it out of the park other doors will open. Then it's crazy because other people will just jump on board, but it's like all they needed was a chance and that's the biggest catch-22 of the situation of just trying to work in Hollywood, trying to hire younger writers, trying to hire people who aren't in the union and who aren't experienced. It's like they'll never get those opportunities if they don't get a chance, and some people get a chance and blow it. OK, but at least they got one.

Did the staff actually roll over from Season 1, or did you have an easier time if you wanted to hire more people of color this time? Was it easier?
We definitely had more of a say and we had more of a sense of what we needed. Television was new to me, so the entire dynamics of the crew, even to hire, I was like, "There are so many damn people here." It was more about me learning like, "OK, how does this operate? What do I need? What vision am I looking for? Who understands it best?" And so now understanding that in Season 2, we were able to sort of troubleshoot to be like what worked and what didn't, and now get a better sense of who we can hire as a result. Happy to say that if you go on set you'll see that there's just all kinds of people from different backgrounds working every job.

I mean, I can definitely imagine it's a huge learning curve going from YouTube to TV, so our background, I work on YouTube and it's, for better or worse, when you put something out you have instant feedback. You know if people love it or hate it.
Yes, yes.

What was the hardest thing or some of the lessons you learned while being in development for TV?
Waiting. Waiting is so hard. I mean, the benefit of YouTube, like you said, is the instant feedback and that you can like, have an idea and just put it out immediately and get the instant gratification. I think for me the hardest part was being like, "I could put this shit out now, like, what's the problem?” But then it forces you to hone in, to make it the best possible. I feel like everything happened for a reason and the timing was perfect.

So then was it easier to do Season 2 because you're continuing the story line? You didn't have to dig deep inside yourself? Or, how did that work this time around?
Yeah, once we did the pilot and I knew what kind of show that I wanted to do, and then of course, Prentice and I, you know, the new show we’re now having conversations with him. We kind of operate the same way. He's all about living, making sure we live life so that we have those stories to tell. And the writers, we mine a lot of people's experiences to make a relatable, real show. Once the characters were down pat, and once I tapped into what I wanted to say and what the core was, it's always harder to come up with stories, just to make everything coherent, because you're making something serial. But I know this world and I know these people, and the root of a lot of the decisions that they make, so it's exciting more than anything. There's nothing more satisfying than breaking a story and being like, "Oh, shit, OK. We're gonna see where it's gonna go from here."


When you're watching the show it always feels like this is a moment you could be having with your friends. For example, the way that you guys addressed mental health and therapy had me dying. Molly getting so pissed off at you that you would even suggest that. How do you make those moments feel so natural?
Just in conversations. The writers' room feels like a dinner party without the dinner, and without the lateness of it, I guess. We're having these conversations about our personal lives. It starts during the day, like, "What'd you do this weekend?" Or, "What's going on with that guy, or girl, you were talking to?" Sharing those personal stories. But with the mental health story, that's just something that culturally we know about a lot of our people; sometimes we use religion to cover up what's going on inside. "Just pray on it. Just pray that this depression will go away." No, you should really like go get treated, or you should talk to someone. Even with the Jared storyline where he dabbled in experimenting with a guy...

Yeah, that was another very relatable one, especially in the world, in hip-hop culture, still not something that’s accepted.
Not at all. Like Lil Uzi, gets a lot of flak currently for wearing—

For wearing a good shirt! I thought he looked great, for the record. I loved his outfit.
Well, that's just something that we want to have those real discussions, and we don't want to take a side either way, because nobody really does take a side, except for you. You said you like the shirt, so you approve, but I mean, it's just those conversation topics to have outside of the show are great. I saw so many people being like, "Would I date a dude who would mess with another dude?" Post that show and I was like, "Yes, progress." But that was something that was a hot topic in the room and then we realized, generationally, it wasn't necessarily consistent. We weren't all on the same page between, you know, black women and white women, between gay and straight, between you know, older and younger, and I find that kind of stuff fascinating and fun to address and talk about.

So is anyone gonna wear a male romper in Season 2, or…? You had to know that was coming.
[Laughs.] Our costume designer, I don't know, she's gotta be for that. I've seen some men look great in rompers. I don't know if Jay Ellis would be down to. He's tall. I don't know.

I think he could do it, though.
Could do rompers?


I just don't know what the scene would be, but that's your creative genius. I'm just here to throw out a suggestion, so who would be your candidate for wearing a male romper in Season 2? Are there going to be new characters or is this someone we know already?
There will be new characters so I think one of our new characters could rock a romper, because I don't know. I don't think that rompers work on tall men.

They have to be short?
They have to be like, average height, and we have a lot of tall men on our show.

So maybe you should consider casting someone average.
You're right.

Look, it doesn't have to be a romper. He could wear other things.
Like what?

Like if you want to look at Young Thug for inspiration, for example. Layered dresses could really bring out his figure.
I don't think we're bold enough. Like, Young Thug can't just walk down the street and pass by. I don't know if we're there yet. Maybe another show we could look for Young Thug as inspiration, and the Uzis of the world, but...

Yeah. We don't have to force it. It's cool.

Just an idea.
Thank you. Thank you, thank you for your creative inspiration.

So I know you don't want this series to be very long and drawn out. We're not gonna see 10 or 15 seasons. How many seasons are you thinking to wrap up this story line in a way you'd be happy with?
I would be killed if I said what I thought, but but they won't be long. I have an idea. But again, I still don't know exactly where the story ends. I know where I want them to end up like, mentally, but I'm not sure yet.

In all of our careers in entertainment, gatekeepers are always gonna be there. So it seems like in college you realized because of YouTube you could do what you want and put it on the Internet and get instant feedback. The same with Misadventures of Awkward Black Girl, and I know some production companies were interested in the series for awhile, but then when you spoke with them they really wanted to change the concept entirely. So is this something you feel like you will be dealing with your entire career, or is it getting easier as you progress?
It definitely gets easier. After a while people are like, "What do you want to do? What can me make? How can we be in business with you?" And then it's just a matter of not being an industry hoe and saying yes to everything. When the door is open it is open wide, and everyone sort of wants a piece, to say that they have a part in this world, and so, and then it's a matter of not repeating yourself. I never want to just go make the same show over and over again. I want to live life so I can have new experiences and new stories. While those opportunities are there, I don't think I'm ready, mentally and life-wise, yet to have a new project that I can stand behind firmly, and so that's also why I'm working with other people who I think are talented. I think it's wise, when the door is open, to bring other people in it. My stories aren't all great. Other people's are, so it's a matter of just putting that on the table for other people to see.

Just to backtrack for a second, you said something that really blew my mind because this is a conversation I've had with friends, but never something I would say out loud, that you feel like, in Hollywood specifically, there are a lot of racist old executives who have to just die for us to make progress. And it sounds really crazy, which is why I would never say it out loud, but I understand what you mean when you say that. So you can hire all the black writers in the world and make progress, but if there are people up there who are just not having it, how far can you really go?
I'm happy to say that we're reporting… To report that we're making progress. People are dying. Roger Ailes just died. He needed to go. It's great, so I mean, as time goes on obviously unfortunately we won't be able to take advantage of it like the younger generation, but it's happening and I feel like there are people in positions of power who wouldn't have had an opportunity in the past who have opportunities now, and who have, like, a firm vision and are intent on hiring the people who haven't been hired in the past. I'm very optimistic on that. Like people die every day, so it's great.

I love that you say it with such a straight face.
It's true. [Laughs.]

I'm sorry. I couldn't not laugh. I couldn't not do it. You never want to model your career exactly after anyone else, right? It doesn't make sense. You're inspired by them. You always want to carve your own path. Do you see yourself heading in the direction of a Shonda Rhimes or do you see yourself wanting to act way more than you're producing content?
I mean, I love—it's cliché but the Oprah model is just dope to me. She feels like she does a lot of work, but she plays a lot. She selects the roles that she's in. I love a mix of Oprah and Tina Fey. I just love writing. I love being behind the scenes. I love producing more than I love being on-screen, but if there's opportunities and parts that I relate to, then I'm down to play them. But the behind the scenes, and even the business side, those excite me way more.


I know you have a lot on your plate, but I just want to throw this out there. You remember that you owe us a project with Rihanna and Lupita Nyong'o. We're all good, right? Don't think Twitter forgot about this, Issa.
[Laughs.] Oh, man. Yeah, that's very exciting. The Internet is a gift.

Don't try to curve me here, don't try to curve me. So this really started with a photo of Rihanna and Lupita sitting front row at a fashion show and someone wrote a funny comment: “Rihanna looks like she scams rich white men. Lupita is a computer-smart friend who helps her,” and they nominated you as one of the people who can make this into a great film, and are you gonna do it? For the culture, Issa, come on.
I said I was gonna shoot my shot, and my shot hopefully will make the basket.

Smooth. I like what you did there. So back to Season 2, I have to ask you about music. I've just been waiting this whole time to ask, because I know you're a big fan. I love your raps. I think it's in like the first few episodes of Awkward Black Girl, you're writing rhymes in your room and you're like, "Nah, it's just too Nicki Minaj." And then in Insecure there's a Nicki Minaj pillow.
There is.

I don't want Our Viewers to think about Trump in any way, shape, or form. I don't want the stink of him on this show. If anything, this is an Obama administration show.

Are there any artists that you might want to have on the show this season? I remember you tweeting that you were listening to Wale’s new album and really feeling inspired while you were writing.
I loved how A Different World used to have these cameos and and unconventional guest stars, where people weren't necessarily famous. I love the idea of doing that for our show. That's something Prentice and I talk about all the time where we don't want to go like, “stunt cast” people, but we had Jidenna on last season and we had Ty Dolla Sign who played himself but was still on it.  I love the idea of breaking new talent but bringing in musicians who are looking to break into acting in roles that aren't necessarily like themselves. I think you see a little bit of that in Season 2. I don't know. Yes, you will see a little bit of that. [Laughs.]

You, you just had to go back deep in your mind for a second.
I remember. Yes, yes, yes, and it's just fun. I think this is new, a new experience for so many of us.

Like you were mentioning earlier, Melina, this is her first TV directing debut. Prentice [Penny], it's his first television show running. I mean, it's my first television show, so to work with actors who it's new for them too is just so fun. It feels like we're all going into this and growing together and that's an aspect that I really love.

Just know that every time you Instagram a picture of Frank Ocean, I'm just expecting him to pop up somewhere, somewhere along the way.
I wish. If I could find him.

So is it too much to ask for you to drop a mixtape? I know you've got the bars. I know you know the people.
I don't have the bars.

What's the problem, Issa?
I don't have the bars.

I've seen the show. You can't lie right to my face.
They're trash raps. They're like emotional raps.

But you're trying to write trash raps. I'm sure you can write great ones if you really wanted to.
Thank you for that, the vow of confidence. I really appreciate that.

So no mixtape?
No. It is a fantasy to like, be on stage and have people knowing your lyrics. Like, I envy that. I just told an artist the other day. I was like, "Can we switch lives?" because I love the idea of just, you're on the stage and people know your every word that you wrote down. That's dope, and I know that I'll never have that.

But only because you don't want to.
That's not true.

That's the crazy thing is no one would be shocked if you really dropped a project, at least one. An EP, three tracks? Come on. We're not asking for too much.
If I get tomatoes thrown on stage, I'm putting you as my shield. I just want you to know that.              

I got you. I promise. I brought this up, like why wouldn't I?
[Laughs.] OK.


Is your mom gonna end up being in this season, and did you give her a speaking role like Melina said that you should?
She asked. I was like, "You were in Season 1 already." She got a speaking role as a potential donor in our fundraiser episode, and so then she asked me before this season, she shot like, "Oh, so what am I gonna do this year?" And I was like, "Mom, you got your… like, you can't just pop up like you were..."

Just let her live.
That's what everybody's saying, but she was in a Mother's Day commercial for HBO.

She didn't want to, she didn't want to say any of my vulgar lines, and that could've been her shot, so you can't like pick and choose in this industry. You gotta choose a lane, and she got her lane already.

Have you always had such a vulgar mouth? I love it, by the way.
[Laughs.] No, not really, because my mom did put like parental controls. Like I didn't go to PG-13 movies until I was 13, and rated R movies until I was 17 and she was kind of strict about that, but I think once I discovered curse words, I just didn't ever look back.

You definitely have a passion for them.
They punctuate things in a way that I can't do with just regular words. I feel very Trumpian in that way, that I can--

Trumpian. [Laughs.]
Like my vocabulary is limited if I don't have curse words to help accentuate that.

I love it. I just think sometimes people, they give me shit about it, now I feel like we're going to start cursing because we're not ladylike enough.
[Laughs.] Yeah.

But I love it. Even the titles of your episodes are so ridiculous. Like, is your mom still upset or does she just accept it at this point?
She accepts it. She wishes that wasn’t the case but she knows like, she can't do anything about it now. She still watches the show. I think, if anything, she's a little bruised that her friends, you know, can't watch and enjoy it the same way.

Just because they're like, "What's wrong with your daughter? Do a better job."

Just give her the edited version. HBO could hook you up I'm sure.
I wish they would. That's a good idea, actually. Maybe they just get them clean versions of the show, like how Sex and the City aired on CBS, and took out all the sex and the curse words and it was a terrible show. Maybe that would work.

OK, never mind. Scratch that one, but speaking of Trumpian vocabulary, has he inspired any of the writing in this show with his ridiculousness?
I just don't want his stench on our show. Because initially there was a, like, you've gotta do something. You gotta make a statement. We gotta like, you know, have something that refers to him, but if we're so lucky for people to watch our show in 20 years, I don't want our viewers to think about Trump in any way, shape, or form. He's not gonna be here for long anyway. I don't want the stink of him on this show. If anything, this is an Obama administration show. It's the result of him being in office and I want people, for his legacy, to be able to look at what he brought to the culture, I want them to say, if he'll have it, this show came of him. It bothers me that there's any association that we're airing during this time, but hopefully it provides an escape.

I really like to make goals lists, right? Every year. I do one to two months, three, six a year, and they change. You have to go in every few months and like update them. If you were sketching out a very rough draft of your goals list for the next year, what would be on there? Look, small things, like I have one month go to the gym three times a week or cancel your membership.

I've canceled my membership. So like say, it could be the tiniest thing ...
Oh, I love that you give yourself an or.

Oh, yeah.
Oh, that's genius. I want to ... Goals? Within the year you said, or the next six months?

Yeah. They could be the smallest or the biggest goals.
I want to have a yacht party or be on a yacht. I want that. I want to travel to Latin America because I've never been there. I want to write a film.

These are great so far. You're doing incredible. Can you write the film while you're in Latin America?
That. I would love to do that.

There you go.
I would love to.

You're stacking goals.
Just stack on, stack on...

Exactly, and then you also wanted to be friends with Sasha and Malia.
I do want to be friends.

You can add that too.
I do want to be friends with them, but now that I've put it out there it's creepy, and now I feel like I've taken out any coolness I may have had. I met Frank Ocean once, but it doesn't count as a meeting.

Because he was leaving a coffee shop and I was going in, and I was like, "I love you" and he said, "Thank you," so that didn't really count.

So you have awkward fan moments too. I thought that was just normal people. I had the worst with Eminem one time. I was shaking. I didn't know, I was just like, "You changed my life, bye." Just got out of there.
[Laughs.] Well, that's what I do too. I'm very much still star-struck. I will not go up to people and talk to them. I just admire them from afar.

OK. “I love you.”
That's all I have.


Photography: Sarah McColgan/Styling: Jason Bolden/Hair: Felicia Leatherwood/Makeup: Joanna Simkin

Latest in Pop Culture