Last Sunday, HBO’s hit dramedy Insecure began its ascension to TV’s sweet hereafter. It’s been a long journey from broken pussies and freestyle rappin’ at Issa’s L.A. flat and these characters know it. “What would you do if you knew everything was coming to an end?” Kelli (Natasha Rothwell) coos into her podcast microphone.
Earlier in its fifth season premiere, Kelli learns that the organizers of their Stanford alumni reunion have mistook her for dead, and while Kelli is usually seen as a foil to the seriousness of her circle, she seemed to take it really hard. She contemplates her legacy—how she’s seen and how she’s lived her life thus far. They’re big questions that the show’s been wrestling with for its entire celebrated run, but the showrunner’s hardly wanted us to feel like anything is actually final. What is a finale but a moment in time where one chapter ends and another begins?
Prentice Penny, who has served as producer, writer and showrunner of Insecure, is quite optimistic about the show’s meaning both within and outside the tube. These sorts of conversations about where a show will end up fascinate Penny up to a point, but his is a more sobering read: “Our show is birthed out of shows like Living Single and Girlfriends. They’re complements. They’re ancestors to this. So I’m excited to see what will be inspired by our show.”
Looking back on its run, Penny’s words spill, easily and lovingly, about the beautiful growth he’s seen in Kelli, Lawrence, and Molly. He was there at the Essence Festival all those years ago when “people could give a shit about what we were doing,” and in the years after where they could barely get through the door.
Penny comes bearing a powerful TV portfolio with shows like Scrubs, Brooklyn Nine-Nine, and, yes, Girlfriends in his back pocket. These shows, and their banter and fluidity, from the ridiculous to the heart-wrenching, equipped the Los Angeles native with the nerve and acumen to take on a production like Insecure. But that couldn’t prepare him for the fun of writing jokes with Natasha Rothwell (please chill on the spin-off talk!), the evolution of Yvonne Orji into a household name, or shooting a brand new season during a global pandemic. There were joyous and difficult lessons learned along the way—like the period between seasons 3 and 4 when both he and Issa took a break to work in film—but each have imbued Penny with a deep sense of gratitude for his cast and how far they’ve come. “They’re getting opportunities now that it took me longer to get to. I’m happy they don’t have to wait as long.”
This interview has been edited and condensed for clarity.
How does it feel to be done with the series?
I’m super excited for people to watch the last season. We’ve been off, not quite a year but a little more than that. I don’t know if it totally feels like it’s over yet because we just started but everything is in these weird steps. Like first, it’s finishing writing, then finishing wrapping, then airing. So I think it’ll kick in when we get closer to the time, but for right now it’s definitely excitement.
The first episode definitely has audiences thinking of the end. Y’all killed off Kelli! She has that whole monologue at the end. Like, what if you knew the end was coming? It’s such a meta question.
[Laughs] Yeah, it’s super meta on top of that as well.
Was that a conscious choice of letting the audience know, hey, the characters kinda know this is it?
I don’t know if we were thinking about the audience with that. It was more like, ya know, the show is ending and they’re also at an age where… the show starts when they’re in their late twenties and the show is now turning to where they’re dealing with more adult decisions. It sorta feels like your thirties set you up for your forties, and so on and so on. There’s a shift happening of how they want themselves to be remembered and where they’re growing to. I don’t think we were that calculated but we were thinking about how the characters were considering legacy.
The cast of Insecure visit Stanford in Season 5
HBOSpeaking of legacy, the cast has been pretty outspoken about the uniqueness of this show in the pantheon of Black TV and TV more generally. In your estimation what sets it apart from shows like Living Single or Girlfriends aside from the HBO-ness of it all?
They’re all just different shows, ya know? They’re shows that have Black women at the core of their main characters and obviously those are two amazing shows—one of which I wrote on, Girlfriends. But in terms of setting it apart, it’s kinda like, what sets it apart from any show, not just those specific shows, you know what I mean? I was actually texting Mara [Brock Akil, creator of Girlfriends] yesterday just how thankful I was. And how working for Mara was a masterclass in just how to be a professional. I was telling her, “You were doing things that we do now but you were doing it 14 years ago.” I remember her talking about how she wanted to make Girlfriends more single camera-y in the moments that needed to be more dramatic than comedic. She was doing all of those things where now it’s just how we make TV, but that wasn’t how we made TV in 2006. I think our show is birthed out of shows like Living Single and Girlfriends. They’re complements. They’re the ancestors to this. So I’m excited to see what will be inspired by our show.
It does feel like this continuation. Living Single was made for its time and Girlfriends was made for its time. Both of them are pushing things forward in their own special ways. And Insecure is of its time. Like the millennial women and men in this social circle who are learning how to age and grow up together. There’s an underlying theme within the first couple episodes where it’s like, when do these people figure it out? And the answer is, you don’t! [Laughs]
Yeah! That was always a big driver for us. Thematically, the characters’ arc from the first episode to the last—Issa needed to learn how to be secure in her insecurities. To know that they never leave you, just learn to manage them in a healthier, better way. You just understand that that’s all part of it. There’s no, “Oh, I conquered it.” We’ll never conquer it. You just find ways to grow and thrive no matter what insecurities you might have. But yeah that’s the point, ya know? That’s what living is. You learn these lessons along the way. It never stops or goes away.
There isn’t a figuring-out point but there are moments in one’s life that changes them. And it’s like, how are you going to respond to this? This season, specifically for Lawrence, he’s starting a new chapter. Where once he could be a single dude hoeing around, now he has a kid. He wants to be a part of that child’s life. It seems like this is the first time the characters are dealing with baby mama/daddy drama. How do you think the show skirts that line of showing the real difficulty of alternative parenting setups between Lawrence and Condola?
One thing that we wanted to show was that Lawrence didn’t plan on this; he didn’t count on this being a part of his life. And what we wanted all our characters, even Issa, to confront was like, what happens when you get dealt a hand that you didn’t expect to play? Do you fold? Do you try to make the best of that hand? For Lawrence, he didn’t count on this. He had a whole plan of possibly being with Issa and having a job in San Francisco. So, what happens when someone comes along and disrupts that? Do you step up? Do you blame others? Do you have a lot of anger and frustration? Same thing for Condola. She tried to play this tough “I don’t need you” role, and we wanted to test that. We wanted to show up honest and real for two people who didn’t expect their lives to end up this way.
Can you recall how the writing and production team approached season 4? It really seemed like a turning point in the show. It just seemed like y’all started hitting on all the things that made Insecure really fucking cool. Centering Issa and Molly’s friendship breakup, it’s not something that generally happens on TV. And also the cinematography. Y’all just stepped it up.
Yeah, a lot of things happened that year. The main thing is we put Issa and Molly’s true love story at the center of the show. Fundamentally, these two women we loved, we got to see a real story around without having men be the driver of the story. It was a huge thing for us to care about in a different way than who they were gonna be with. It’s about the love story in peril, so it changed things. That season, Shiona Turini, our costume designer, came in halfway through season 3. She got to be there for a full season and set different looks. That was a time that Issa and I took a break from the show to make movies. We both came back renewed.
And from a directing standpoint, I grew a lot directing a feature [Uncorked], and I wanted to bring more cinematography, more things we don’t normally do in our show like shooting in silhouette or in slow-motion. Shooting in one take without cutting. And even being a better director telling stories. Normally, that last scene [in season 4] with Issa, Lawrence and Condola, we might’ve made the Condola scene one long flashback. I was pitching it as we should cut back and forth so it can seem like one conversation. Because visually that could be really interesting, and each other answers the other’s questions and we don’t really know where we’re at until we’re in it. The audience won’t know when you’re cutting out of something so we could use that for impact. But I don’t know if I would’ve thought of that without directing a movie.
Yeah, it seems like there’s this great combination of continuity and these bursts of new people, new ideas. I remember watching that season and just being like, oh, y’all have figured it the fuck out completely. Just a total cinematic experience. The movie that you’re talking about, though, that’s Uncorked, right? Were you just picking up tips from [cinematographer] Elliot Davis or [editor] Sandra [Montiel]?
I had worked with Sandra on Happy Endings and Brooklyn Nine-Nine and she’s such an awesome editor. But definitely I learned a ton from Elliot Davis, how could you not? The guy has forgotten more about movies than any of us will ever learn. Like, he was the first AC on the first Dirty Harry movie. Shot Out Of Sight. The guy is amazing. He always encouraged me. Every day we would sit in a cafe and talk about the script, talk about ways to visually push the imagery. We would talk about what the characters are feeling. We’d talk about movies like Last Tango in Paris and then use those as reference points, whereas typically on a TV show you don’t have the time to do that. And the show is already set, the look of the show. You can play a little bit but still have to honor what came before it. In a movie, nothing existed before or after this so it can be whatever it needs to be. That’s the difference; that’s the fun part. I learned so much from Elliot I wanted to bring back to the show to help how we told stories visually. This season too, like thematically, I’d watch other movies to help. Like one episode, I feel, is a Western.
Really?
Yeah, you’ll see when it comes out later. I watched a lot of John Ford, a lot of High Noon and Fistful of Dollars because thematically, that’s what was happening. So I wanted to lean into that feel. We shot it a lot like a Western.
That’s really fascinating.
You don’t watch Insecure thinking Western! When that episode airs there are a lot of things that are Western-y about it.
So, just coming back to the first episode, first off, RIP Kelli. For them to come together and for Issa and Molly to reunite and to sorta work up on their friendship, what was the choice behind that? Because it really could’ve gone either way.
We did want to honor the fact that they wouldn’t be fully together just because they talked a little bit. It’s like a broken bone—it takes some time to heal. In the writers’ room we used the analogy of an athlete breaking a bone and they haven’t tested it in a while, [so] they had to come out of the game. And so they’re nervous about coming back in and doing that move. They’re nervous their knee won’t hold up the same if it gets hit or whatever. And it’s not until you get your first shot, or dunk, or tackle to know, like, hey, my leg’s okay. We always measure whether Issa and Molly are okay based on the hijinks they get into, whether it’s broken pussy or the “wine down” fire or the Lyft fight or at Coachella being high. There’s always some sort of crazy thing they have to go through together that they can look back and laugh about. They aren’t really right until they can crack jokes on each other without worrying, Did I offend you? That’s the whole season, them finding their way back, recognizing that their relationship is fragile—and what I mean by that is that, just like any other relationship, it can be damaged if you don’t nurture it. They thought that their friendship would just last without thinking, no, we have to be intentional. We have to put in real work in this relationship. But that’s something you learn as you grow older too. Hey, I have to be intentional or it may not survive.
I was also thinking about Kelli. Whereas I think the Kelli of season 1 might’ve been able to laugh off Stanford killing her, it does seem like it takes a real toll on her. It’s one of those meta things because viewers are like, Kelli is so fun, she deserves her own spin-off. But then the Kelli within the show is reckoning with being a side character. What was behind that choice?
People keep asking if she’s gonna get a spin-off. I keep telling people Natasha is at Disney now. [Laughs]
Issa Rae in Insecure Season 5
HBOYo! She’s not checkin’ for no spin-off! [Laughs]
Knowing Natasha, she has so many other things she wants to do. I think she loves playing Kelli; she’s doing movies and White Lotus now. She’s doing fine. It’s a real testament to her wanting that because her performances are all great. In the room she always gives us a ton of comedy to use for the show. But over time you don’t wanna just be that. I think it’s different when you’re the one controlling the joke. I think that’s what happened. Again, it’s about legacy. She was wondering, is this how people really see me? A reunion is a good time to get a sense of how you’re seen. It was only the second time we got to rock Kelli—the first being when Tiffany left her off the baby stuff. We wanted to give Kelli a journey that could take us through the whole season even if she doesn’t get a whole episode. This arc will continue to play out all the way through to the end. It’s nice to see her journey and to give her real stuff.
In addition to the casting of Black actors, it seemed to me that people are responding to the leads of the show being dark-skinned women. Issa and Yvonne are both supremely talented but was it significant to you, maybe after the fact, that dark skin was not only getting great lighting, like hello, but also such a massive response?
That was our intention—to cast a dark-skinned Black woman as Molly. From the beginning. In real life, Issa’s friend who Molly is based on is dark-skinned. That was always the goal; always the plan. Props to Issa because her point was you never see two dark-skinned Black women in these roles that are the core of the relationships. You might see the Issa character with natural hair but the Molly character might be the fairer one. And the second she said it, I was like yeah exactly, ya know? It wasn’t even a doubt or a question. I’m glad that people love it too.
How’s it been watching Issa and Yvonne and all these folks grow over time?
In some ways Issa and I are like big brother/lil sister. But in other ways I feel very parental about them. Even when I first met Issa, I knew she was going to take over the world one day. Just like hearing her dreams and goals. And I’m a dreams-and-goals person, but she even got me beat. So seeing her do it is not super surprising for her own stuff. What I love is how she got to be embraced as a dark-skinned Black woman cover girl. The fact that she got to be the voice of the NBA last season. I think Yvonne, even more so, no one knew who she was. I remember walking down through the Essence Festival, we were showing the pilot, and people could give a shit who we were. [Laughs] Nobody knew what we were doin’, why we were there. Then 365 days later, we couldn’t walk anywhere. The screenings were sold out. We had to be ushered off through the festival; it was a madhouse. To go from no one knows who we are to people screaming, Lawrence! Molly! I’m super proud of all of them and their outside endeavors too. Everybody’s doing stuff that has nothing to do with them being actors. They’re getting opportunities now that it took me a lot longer to get to. So I’m happy now that they don’t have to wait as long.
How was it watching Keke Palmer slide into her role as Condola’s sister? Did it come about as easily as her sending a tweet, forreal?
It was literally exactly what Keke said: her sending a tweet and us saying to Vickie Thomas and her team, yo is this real? So we called and they were like, nah it’s real! It was funny that she ended up playing Condola’s sister since most of her shade on the show was about Condola. And she was like, I didn’t shade you I just hated the situation. [Laughs] It’s so crazy because they’re great together, as you’ll see. Keke is just awesome.
Wade Allain-Marcus, Jean Elie, Leonard Robinson, Yvonne Orji, Issa Rae, Christina Elmore, Jay Ellis, Prentice Penny, and Courtney Taylor attend the after party for the premiere of HBO's Insecure Season 5 on October 21, 2021, in Los Angeles, California.
Amy Sussman/GettyThere’s been a healthy dose of drama outside the purview of the show itself. How does the squad maintain focus in the midst of everything?
Internal stuff—we haven’t had anything on our side. Nothing that I’ve seen. In the world of making a show during COVID, it was super difficult. The beginning part was tough because you’re used to walking up to actors and having conversations. You couldn’t move how you moved in the beginning. Like to give a note, we’d have to wait and clear things. The process was just more of a grind. But once you start doing the scenes, then you’re just doing the work. That was the reprieve from it. We wanted to end the season with directors that we called our faves—not that we didn’t love all our directors. We love Melina [Matsoukas], Ava [Berkofsky], Kerry Washington, and me, but we also wanted to give Natasha [Rothwell] and Amy [Aniobi] and Mo [Marable] and Kevin [Bray] a shot. We were glad we did, because last season we had different directors for almost every episode. This year that wasn’t as possible. But the great thing is that we’ve been together for five seasons and six years, so everyone knows how we function together. For that part, I would say it was easier than if we were a new show. I think everybody was excited to go out in a great way and focused on doing our best work. That was the easier part.
One of those weird inversions where we know it’s going to be harder to shoot the season but because the chemistry is so good you can just ease into it.
If it was not the last season it might’ve been tougher. But honestly, I think that because it was the last season we went into it like no one wanted COVID to win.
