‘Insecure’ Creator Issa Rae on Comedy in a Time of Crisis: ‘We Are More Than Our Trauma’

TheWrap Emmy magazine: “We don’t really get a lot of television shows that promote Black beauty, Black art, without having to have our burden be front and center all the time,” exec producer Prentice Penny says

FOR MAGAZINE USE ONLY Issa Rae and Prentice Penny
Matt Sayles

A version of this story about Issa Rae and Prentice Penny first appeared in the Drama/Comedy/Actors issue of TheWrap Emmy magazine.

There’s nothing normal about this year’s Emmy season as we face a global pandemic and, in recent weeks, a national uprising against systemic racism and police brutality. With this latter upheaval in mind, TheWrap asked two of the creative forces behind the HBO comedy “Insecure” — creator, star and executive producer Issa Rae and executive producer Prentice Penny — to discuss this moment in history with one another, and to share their own experiences of George Floyd’s death and the subsequent protests. They also reflected on how “Insecure,” rooted in the Black experience of Los Angeles, fits into this context. The conversation took place on June 22 at Rae’s studio in South L.A. (It has been edited for length and clarity.)       PRENTICE PENNY Our show came on at a very specific time in history. How did it feel to watch as real life was also playing out on a week-to-week basis? ISSA RAE Initially during the pandemic, I remember feeling the pressure and the expectation and the anticipation to come on, and it was kind of a blessing in disguise because people were at home and ready to watch television. And then of course during the racial unrest and George Floyd’s killing, and the surrounding angst and anxiety, I personally felt anxious and generally worried and was obviously grieving, and it just felt like everything that we were doing was futile. It just felt useless and self-serving to put on a television show during this time. I remember, we had our conversations, some cast members and I are on a group thread saying, “What are we doing? How do we go protest? Do you guys want to go out today?” And luckily we had a conversation with HBO about the messaging, because we couldn’t stop the show from airing. What I found was so many people needed this to air and wanted to escape for 30 minutes because the city was being torn apart. And the episode that aired during the weekend when people were out protesting was specifically about Black love. It was watching two Black people take ownership of themselves and their feelings and looking towards the future, and it was a reflective episode that I think was perfect for that time. From that moment forward, people found solace in our show, and I took solace in the fact that people took solace in our show.     PENNY For me, what I’ve always enjoyed about our show is this idea of, even though it gets into things that are obviously about race and things that are happening, it’s really there to promote Black beauty. We don’t really get a lot of television shows that promote Black beauty, Black art, without having to have our burden be front and center all the time. I think that’s what’s beautiful right now, especially where we are in the world when people of color, specifically Black people, aren’t really seen as having humanity. What I love about our show is we talk about that without having to have a message. Just the fact that Issa gets to exist in the world, that a character like Molly (played by Yvonne Orji) gets to exist in the world is just saying it without having an episode so-and-so. RAE Navigating life as Black people, you don’t have a slow-motion moment when you experience trauma. It’s just, “OK, this happens to me and how do I process that?” That is being Black. It’s all these obstacles — so much to overcome but you keep pushing, nothing stops for you and I think that’s what our show illustrates. PENNY If you think about the first season, we would have these microaggressions of Molly at the office where she has to be told to tell the Black worker, “Don’t be so Black.” But now, seeing these white actors do these PSAs about what they’re sorry for and things like that, everybody’s in some way coming to this funny awakening that racism is a thing. Our show was showing these microaggressions before.     RAE I think it’s also funny that people watch it and non-people of color were like, “Oh, that’s not me, that’s Freddy, I’m glad that’s over.” It’s been an awakening for so many people that, Yes, racism is here. Yes, it exists in California. Yes, it exists everywhere. You can’t be in a bubble — and if you’re in a bubble, it’s by choice at this point. Specifically with this season, even tackling the destruction of a friendship — which I haven’t see in a lot of television, much less in Black television shows — we get to focus on the mundane. We get to focus on the paper cuts. It’s not weighed heavily by the outside burdens of the world, we really love to do these small character studies. And I think that’s the fun of this, to live in the small. PENNY Because right now everything feels so big, but if you think about it, this is just as small. The guy (in Atlanta) was just in a drive-through and that’s such a small thing, right? In all these situations, they all start so small: Someone is just jogging home, a guy is in the park wanting to film birds, and then it becomes giant. I think we’ve always tried to make our show feel small because that’s where things become more universal. RAE We’ve been out there protesting, using our voices, and I think especially during this time it feels like everyone’s listening. I think about the photos in history books of people being out there and putting their lives on the line. I think about someone like Kendrick (Sampson, who plays Nathan on “Insecure”), who does this daily — he’s been about this life for such a long time and he’s using his platform in a way to bring awareness and people are actively listening and he’s become a leader in this space and I’m so proud of him for that. How have you been feeling personally in grappling with everything that’s been happening?     PENNY It’s horrible! It’s soul-crushing in so many ways, but also beautiful in so many ways because it’s prompted conversations. A lot of Black families have had conversations with their kids about the world, and kids are trying to process those things. So there’s the part I feel as a man, there’s the part I feel as a father and as a husband and as an artist. Each of those has been hurt in a lot of ways. But also the other part of me is excited and curious and scared: Where this is going? Because so much of my parents talking about the ’60s and what that time was like, was so defining for so many people and a generation. Whether they were like, “We’re going back to Africa, we’re going to build black schools…” I was born in a time in the ’70s and ’80s where you started to see the Reagan stuff come along, and I was always curious where that energy went. You see those pictures in the ’60s and you look at today and there’s a lot of that energy now. I know all the ways it’s going to be horrible. We all know, but it’s a new feeling for some people. Black people have just been exhausted, but I think for more non-people of color, it is a new thing for them, it is a new feeling for them, it is a thing where they go, “Oh, snap, is this the world we’ve lived in.” So for Black people, you can look at our show and go, “Oh, yeah, we’ve been talking about these things since the show came on,” but just see us as people. I love that people are coming into their awakening, but we’ve always talked about that racism in this country is a comma for black people: “Oh, I got discriminated against by the cops, but comma, I still have to go to work…” “This slight happened to me, comma, I still have to pay my bills.” So what I love is that our show is trying to see our beauty, see our strength, that we can have scenes that go from dramatic to comedic to heartbreaking and back to comedic and that’s showing us at our full spectrum. So in all the ways that it’s horrible I’m trying to find how we … not move past it but move through it in a way that good things will come out of for us on that side. How about you? RAE Even hearing you talk about the ’60s and where’d that energy go, it speaks to how I was feeling at the time. Specifically as it relates to our show coming out, it felt like this moment is so important where people are finally listening and their ears are open. It feels so precious and I’m just, “We can’t f— this up!” Is the show a distraction? I don’t want to take away from the messaging and the focus at hand because people are so willing to be distracted so they don’t have to think about it while we’re living in this. A lot of my anxiety came from that. A lot of my soul-crushing anxiety came from, “Please make this moment matter,” because — to your point — so many of our elders have been through this time and time again and been defeated time and time again. I guess I get tired of incremental progress and I just can’t take the heartbreak if we’re back to more of the same. PENNY I’m curious how it’s also going to impact the industry. Obviously, we work in an industry where we’re not a lot of the gatekeepers deciding what gets on the air and what doesn’t get on the air. So I’d be curious in a micro world, where we work and make our living, is this going to open more doors for heads of studios? Is this going to open more doors for people who can say yes or “I get that, you don’t have to explain it to me?” I’m curious if it’s going to open showrunners’ eyes to “Hey, I don’t have to just count the one Black person in my room.” I’ve been on those shows, where you can watch other white people continually get hired and you’re still just the only Black person here. So I’m curious: Will our art be taken as seriously as everybody else’s?     RAE Or will it be defined by pain? I think that’s the other part of it. Are people going want to see more of this time, and are they going to want to contextualize it in a way that still puts our pain as the sole identifying factor of our identity? We are more than our pain, we are more than our trauma, we are human and we want to showcase human experience. PENNY I think one thing that people like about our show is they can relate to Issa, and you see a Black female get to be the awkward, uncomfortable one. Usually that’s been a role in Hollywood that is a white woman’s role. Our show shows that clumsy and awkward is not a unique white trait… RAE You don’t get to own that, too! PENNY Yeah, you don’t get to own awkwardness. I hope people see the full spectrum of that in all of our show and all of our characters and the world we’re painting. RAE We’re in the room for Season 5 and we’ve had a lot of conversations about whether or not we want to showcase what’s happening now, specifically with the COVID of it. Do you want to talk about where we are with that? PENNY We’re obviously in the real world. The show came on when Obama was at the end of his term and we would never really say “Obama,” we would always say, “in this climate.” Even when Trump got into office, it was always, “in this climate.” Going forward with the pandemic and racial stuff, it’s changing day by day and we write our show and produce it almost a year out from the time it airs. Who knows what will happen? So I think that’s the balance we’re trying to find. We don’t want our stories to be solely defined by those things, too. So sure, we might see some people in masks in the background or people on our show might have hobbies all of a sudden that they didn’t have before, or certain abilities that they didn’t have before. But we’re trying to find that… I think race has always been a part of our show so that doesn’t feel like a new element, we don’t have to be like, “How do we incorporate that?” For us, a lot of those elements don’t necessarily change. What do you think? RAE I think about the L.A. of it, because our show is so rooted in L.A. L.A. is a character in this series, and (I’m) thinking about the Black businesses that we showcase and obviously the specific communities and even our main character’s chosen passion and profession, which is very events-heavy. I want people to be able to watch this show 10, 20 years from now, so I don’t want to feel bogged down by this. But it’s always going to be a balance. We don’t want to lose the journey of the character of Issa — I think that’s the most important thing. What I want to see as an audience member is just, “Is this boring?” I think there’s an element of making what we want to see and not necessarily changing that. Read more from the Drama/Comedy/Actors issue of TheWrap Emmy magazine. Drama/Comedy/Actors cover