Prentice Penny has been prepared for the end of Insecure for a while now. The showrunner has worked with Issa Rae for five seasons, guiding her comedy about the friendship between Black millennial women in Los Angeles to a conclusion that feels right for the show’s characters. “I’ve seen a lot of shows go past their expiration date, which we never wanted to happen,” says Penny, 46. Still, Insecure’s end is a bittersweet moment for the producer, writer, and director: He’s helped create something he’s very proud of, but laments that he won’t get to work with this group of people, who he’s grown very close to, anymore.
Insecure is important to Penny because it’s a show he knows probably wouldn’t have existed 10 years ago, even though it has parallels to the show which helped him break into Hollywood nearly 20 years ago. Penny got his start in the writers’ room of Mara Brock Akil’s Girlfriends during the mid-aughts. After the 2007-2008 Writers Guild of America strike dealt the show its death blow, Penny moved on to the likes of Scrubs, Happy Endings, and Brooklyn Nine-Nine, working as a writer and producer. During that post-Girlfriends period of his career, he was the only Black writer in every single writers’ room, right up until he signed on to run Insecure. It’s an experience that stuck with him, and he hopes Insecure’s success will make it less common. “It should be better for the writers that come behind you and I’m so happy Insecure got to be a bridge for that to happen,” he says.
Insecure is at the vanguard of Black art that surfaced around the middle of the 2010s and gave rise to more opportunities for Black creators. And while this development has been fortuitous for those who made it through the door, it underlines the racism of an industry that only inches towards “diversity and inclusion” in the interest of profit. Although Penny can see how things have changed and still wants them to be better, he’s been in the game too long to be unrealistically optimistic about its future. Regardless, he’s still looking forward. His first feature film, Uncorked—which he wrote, directed, and produced—was released last year. He helped create and served as an executive producer for Pause With Sam Jay, which premiered on HBO this year. And just a few months back, he moved his overall deal with HBO to Disney’s Onyx Collective, where he’ll create and oversee projects across various Disney platforms.
Penny spoke to GQ about steering Insecure to the finish line, the show’s explosive Lawrence-Condola capsule episode, the future of Black art, and more.
How do you feel about something as seemingly innocuous as Tiffany, a fictional character, wearing her pink and green and an Alpha Kappa Alpha shield because she’s a member of the sorority—on the fictional show—sparking this ongoing conversation about whether or not that was disrespectful to the organization, to the point that even Melina [Matsoukas], who directed the episode, felt the need to address it?
I don’t know, that’s up to them, because there are people who feel…a way. I’m also a member of a Black Greek Letter Organization, so I think we’ve always tried to represent them well. It’s not anything that hasn’t been on our show before—it’s been on our show since 2016, in the first season, when Molly was drinking out of AKA mugs and wearing an AKA shirt—so I’m not quite sure where this is all coming from now, specifically. But I guess those people would have to explain why it’s a thing now, but I don’t really know to be honest. I’m done trying to guess why people do what they do.
The Issa-Molly tension that we saw boil over last season had been simmering for years. Can you tell me about the importance of showing conflict in a show that’s about Black women’s friendships?
Issa and Molly were always real friends and I think that’s different from some shows where the friends are frenemies. I think on a show like Girls, the characters were more frenemies, whereas we never wanted to pit people against each other. Every season has always built on the season before, so for us, it felt like it was time to dissect that friendship in a specific way.
One of the themes that we did last year was: “Are people in your life for a reason, a season, or a lifetime?” And I think we felt like we couldn’t explore that topic without exploring the Issa-Molly friendship in that same way. We wanted to highlight the true love story of our show: [the relationship between] these two friends. The beauty of their friendship is that they have this shorthand with each other because they know everything about each other—but that’s also the tough part about a friendship: when somebody knows everything about you. So if you’re wanting to grow in some ways, sometimes even if friends are well-intentioned, they can still remind you of your mistakes. And maybe sometimes that’s not what you need or want to hear. For us, it was about getting to the core of that relationship and seeing, for all of the characters, who was going to be around for a reason, a season, or a lifetime.
I’ve seen pretty much everyone involved with the show say that one of the main themes for this season is: “Are we gonna be OK?” And you could feel that early on in Issa and Molly’s interactions. It takes them getting robbed in Oakland—the type of chaotic experience they’re kind of familiar with—to get them back to where they were. How does that theme loom over the remainder of the season?
I think it was the first kind of serendipitous moment where what the characters were going through is what Issa, myself, and the writers were going through as well. Are we going to be OK now that we’re not going to work together in certain ways anymore? I think we wanted to ask that question of all the characters: Are we gonna be OK if we have to co-parent together? Are we gonna be OK if the man I want to be with isn’t? Are we gonna be OK if people see me as a joke? Am I gonna be OK if I can’t get out of my own way in relationships? Condola, Lawrence, Nathan, Issa, Molly, Tiffany, and Kelli are all wrestling with that.
I talked to Jay [Ellis] recently and he mentioned that one of the themes for the final season is whether anyone can really “have it all.” To your point, that applies to every character. Issa has her career a little more together now externally, but she has imposter syndrome. Molly’s career has always been in a good place, but her personal life has always been a mess. Now Lawrence’s career is in a good place, but he and Condola are having issues co-parenting, to say the absolute least. How does the concept of “having it all” manifest beyond that throughout the remainder of the season?
That’s the thing: Issa always talks about how you can’t control the cards you’re dealt, but you can kind of control how you play them. All of these characters are in the same early 30s space where so much of your life has kind of already been set, but you also still have so much ground in front of you, and you’re still in that place where you think: “By 25 I want to have this and by 29 I want to have this.” It’s good to have those markers, but you can’t treat them like hard and fast rules, and I think these characters are discovering that the older you get, the more those markers move.
What does it mean to “have it all,” right? And I think people tend to think that literally means “have it all,” but I think for us, it’s about defining what “all” means. We kind of did that last year with Issa and Lawrence where he’s like: “You make me happy. Happiness is a choice.” So then it’s like, “OK, let’s test that.” If it’s a choice, then these are the choices we’re going to make as a result of that. Basically, I think it’s all of these characters redefining their legacies. What do the things they said they wanted actually look like in practice? It’s one thing to say it in a vacuum, it’s another to have to live it out and I think we’re trying to have the character figure this out.
You mentioned Kelli, who’s always been a reliable and sobering source of comedy. But this season, you see her dealing with the toll of being “the funny friend.” Was that in response to any criticism about Kelli’s character being one-note—for the record, I don’t think she is—even though she is funny and Natasha Rothwell has been great in the role?
No, none of it was in response to anything social media-related. We’ve always wanted to give Kelli more story, it’s just that our show is a half-hour—or 28 minutes, for people who throw shade. Issa’s the sun, so the further you get from the sun, the darker or colder the story becomes, so it’s hard to give Kelli her own individual story unless it’s somehow affecting Issa or Molly. As much as we may want to expand that, it’s difficult because, unless it’s affecting Issa, it’s not really as relevant to our world. We talked about doing a separate Kelli story with like, three separate storylines and we’d have 10 minutes to tell these mini-stories, but we couldn’t figure out how it would all connect to our main characters.
I think if we had another season then we could use an episode like that, because we’d have the space, but we just didn’t have the real estate to take the longer route home while trying to end the show. But we did figure that we could give Kelli a mini-arc at the beginning of the season that addresses these things, so even though it might not be her own storyline, we can use this jumping-off point as a way to explore things for her. That was our happy medium of giving Natasha something real—the show’s dealing with legacy, Kelli’s thinking about legacy—that the character gets to explore throughout the season.
You know that would probably make even more people say Insecure should be more than 30 minutes, right?
Well, they can go make their own show. We’re done with ours [laughs].
Insecure has made what I think is a wise decision not to address the pandemic. Logistically, it just wouldn’t work within the narrative. But, was having Kelli think about her own mortality an intentional decision considering that a lot of people have had to do that, in some way, during the pandemic?
I’d say no. It was only May of last year when we started the writers room, so it was so early that I don’t think any of us really knew where that was going, specifically. We were starting to talk about things independent of the pandemic, and I think the more we kept writing, the more we started thinking about whether we should do it. We were also starting to see people selling all of these pandemic shows and we agreed that by the time this season came out, people would want a break from all of that.
I think when we had the episode last season where Issa and Lawrence are on their date, that came out around the same time as all of the George Floyd and Ahmaud Arbery stuff and people really wanted a reprieve from all we were watching on the news. People were thankful that it was a nice break from that, and know that these characters are in the world, but it’s also kind of a break from the world. So we decided not to do it—and this was pre-vaccine and everything. Once the vaccine came out, we were so thankful we didn’t do anything pandemic-related, because for a while we were wondering if we’d seem so tone deaf [by not addressing it] because we were all living it.
The one thing our show has tried to do is never fully address the literal things. Even when it went from an Obama presidency to a Trump presidency, we thought to address the fact that things were different at the moment regarding the climate, but the show isn’t a documentary or a platform for those things. However, it does have to address that things are different, so that’s why there’s that speech in the beginning in the car where Tiffany, Kelli, and Derek are talking about the way the world is right now. We’re kind of hinting at what we all know, but without showing that they have to wear masks and everything.
I think people would be exasperated if Insecure became a “pandemic show.”
I also think it would feel very dated when people look back on it. People would be like, “Why is it like that?”—and obviously we’d all know why, but I think it would just take from the world the show exists in, even though we know it’s in this world.
I asked Jay this and I feel obligated to ask you as well: What do you make of the resentment towards Condola, who was introduced as the perfect foil to Issa, for supposedly standing in the way of Lawrence and Issa being together?
What did Jay say?
He said all of you viewed Condola as the “adult in the room.” She’s the one who made everyone get their shit together. You can see the big step up in Lawrence’s presentation between when he was with Aparna, then when he was untethered and trying to be the playboy that he absolutely isn’t, and then when he was with Condola. He was far more put together because she is. Condola even made Issa feel like that’s the level she needed to be at. Then it’s the irrational nature of people projecting their whatever onto the characters because everyone has a war they want to fight.
For sure and I think that’s a great answer. It’s a testament to Christina [Elmore]. I think it’s a few things, though. One is how you initially meet her. Some people have an objection to anyone they meet who has their shit together in general and I think obviously because the audience is kind of in Issa’s view. I’d be curious to know how people would feel if she never dated Lawrence—like what if she was just another character in our world? I don’t know that people would feel like she’s so bad, or at least bad in the audience’s eyes.
In addition to the introduction of her dating Lawrence, our main character’s ex, Issa’s kind of putting Condola ahead of Molly. So she’s got your man and you’re putting her in front of your closest friend, and then she gets pregnant by Lawrence. Then it becomes: “See, that’s why I never liked her!” There are all of these layers people wrestle with regarding Condola, even though she’s not engaging in any of that energy at all. I just think that by proxy of how she relates to our main character, people are just checked out—like, “Nah, I don’t like her.” Then when the pregnancy happened, it ramped up.
It all reached another level when everyone found out she was pregnant.
Because they had broken up. So there was literally no threat of Condola until that news came out. She was gone by episode five, so there was no reason for there to be any backlash against her. She was out of our characters’ world.
In the Lawrence-Condola bottle episode, you see his inability to see things from her perspective. What he’s experiencing—having to commute back and forth between San Francisco to L.A. every weekend to see his newborn son—is difficult. But if it’s hard for him, then imagine how hard it is for Condola, who doesn’t get a break. Also, Lawrence doesn’t like being seen as “the bad guy”—which is exactly how Condola’ sister sees him. Can you tell me about the decision to have his life flash before his eyes, in a couple of ways, at the end of the third episode?
I think it’s that thing where you hit some sort of…whether you want to call it “near death” or certainly something that rattles you in a specific way. One thing we always talked about in the script—and there’s no verbiage to this, but it might have been in the scene description and we definitely talked about it in the room—is the point of legacy. How are you going to be remembered? That moment wasn’t just about Lawrence, because Lawrence has someone he’s leaving behind, so what is he leaving behind? Is his son’s memory of him going to be him fighting with Condola? Is it going to be him not coming down to see him when he said he would?
That’s the legacy of Lawrence: him realizing that he’d be the guy who left a son without a father. And even though it wouldn’t be his fault, was he doing everything he could—at the highest level, with the most sacrifice—to be there as a father? And I think Lawrence wants to be remembered as more than that. Going back to “Can I have it all?”…can he? Can you be a single father living in San Francisco with a son in L.A.? We don’t know, but you have to decide what the “all” of it is. If that’s the priority for you, then you’ll do that. If being with your son is the priority, then you’ll do that. And I think that’s the dilemma we wanted Lawrence and Condola to face, because that’s also her story.
Here’s this woman who, at the end of last season, was obviously hurt and probably still wanted to be with Lawrence, but basically told him that he didn’t need to be involved. She was trying to be tough in saying that she didn’t need him, but this is what it looks like when you say that. This is the table you’ve set as the result of trying to be hard, and here’s what it looks like. I think both of those characters realize that they’ve taken their anger and pettiness towards each other too far and it’s gotten in the way of what their new responsibilities are. So I think we wanted both of them to reach a humbling place where they go from two people who did love each other to threatening to get lawyers involved—but that’s real. That’s so real. We were all sharing stories of friends of ours who are in those situations, so we thought about how we could do that for not only Lawrence, but for Condola, too. It’s really their episode, together.
I went back and watched the episode from season four where she tells Lawrence that he doesn’t have to be involved, but I think that’s probably much easier to say before the baby’s born and you’re still able to sleep through the night.
Exactly, it’s a whole lot easier. Condola’s the kind of person who talks about feeding the baby organic food and how she’s going to cook the baby’s food, but once the baby comes, sometimes you don’t have time for that. In the writers’ room, we always said that Condola probably thought it was a situation where she’d have a lot of control because she’s very measured and in control, but it’s not. We wanted to test her “You can be as involved as you want to be” comment.
There are people who think Lawrence should have been written out of the show after season two and that you’ve been reaching to keep him around—especially now that he’s moved to San Francisco. Why did you decide to keep him around for the whole ride, save for that pump fake at the beginning of season three?
For us, it was important to keep him around for a few reasons. We felt like the character of Lawrence was interesting because on other shows, I don’t think you get to see Black men in different ways. Lawrence was always a way to have Black men still be part of this world where they also get to be fully-realized, three-dimensional characters. So we decided his story should stay relevant, but we also opened the door for Daniel’s story—what’s he like? What’s Nathan like? They’re all something very unique and specific, but I think Lawrence more so than anybody, because I think when you typically see Black men in other shows, they have to be the cool guy, the style guy, or whatever.
He’s kind of the photo negative of Issa in a lot of ways: a guy who’s not the coolest, makes mistakes, and is trying to figure it out. So I’m really happy that we kept Lawrence around because it’s allowed the show to breathe [in other ways]. Even beyond the romantic parts, because when Lawrence wasn’t tethered to Issa, we let him go. That’s why he’s gone at the top of season three: because she’s living with Daniel. There were no Lawrence stories to tell because he’s not in her orbit, but around that time we also started to identify some areas we wanted to explore in season four. That’s why it felt like, “Oh, this could be an interesting thing we can layer into season four.”
We always knew we wanted to bring Lawrence back somehow so he and Issa could have another shot. Season four felt like the right time because usually when a woman cheats on a man, the guy is like: “I’m done with her forever.” We decided to explore Lawrence owning that he participated in the demise of their relationship and what would it look like if he had some time to step away from it, because he loved her. So we always knew we would bring him back, it was just a matter of figuring out how, but having them give it another shot gave us more to talk about. Can they bounce back? That’s something Lawrence talks about with Chad and Derek.
Speaking of Derek, I’m pretty sure I know what you’re going to say, but I have to ask this anyway: What happened between him and Tiffany? There are theories that Tiffany cheated on him and that the baby isn’t his.
All of those theories are wildly incorrect. They were only separated; that’s it. It’s Derek’s baby, she didn’t cheat, nothing happened. We never even gave them that much of a back story, but they had some hiccups and he went to go live in a hotel during their little separation, but it was never because somebody did something. It wasn’t even that deep in our minds, but to the point of where Tiffany was at during the [season four] finale, we’re always trying to show what it’s like in real life when friends hang out. Even though you see the four of them together, it would be much easier for the three of them who are single to hang out than Tiffany who’s married and has other responsibilities. That’s just being realistic. So sometimes Tiffany’s not around, but it’s funny when people start theorizing about why someone isn’t around.
When it was announced that season five would be the final season, I had a debate with some friends who argued that you all should take the Curb Your Enthusiasm approach and just keep the show going for as long as possible, even if there were extended breaks in between. I disagreed because Insecure isn’t that type of show, first and foremost, and I also don’t think we need to follow these characters for decades. Why does ending Insecure now feel right?
Issa and I always said it was going to be five when we first started making the show and I agree with you. Not every show can handle a lot of episodes, sometimes you’re just there for the journey. We wanted to leave when people still loved the show. I remember when Empire first came on and it was like nine episodes, it was great because you could do so many interesting things. But when the network saw that it was a hit it became, “Let’s make 20 of these.”
That’s cool, but the structure of that show couldn’t handle one-upping itself every episode. It started jumping the shark because the way that show was constructed, story wise, it couldn’t handle but so much of itself. It thrived in a certain system and I feel like when other shows start to change their system, they start losing what’s special about them and start doing things that are contrary to the best way to tell the story. For us, it was always about the best way to tell our stories and Issa and I always knew what the thematic ending of the series was, and we were getting closer every season. I don’t even know how we would’ve done a sixth season because I feel like we’ve told every story we wanted to tell.
And as someone who lived through the 2007-2008 WGA strike, wouldn’t you agree that it’s better to end things on your own terms?
Oh, 100 percent.
To me, Insecure has been about growth—literally the Kelli “Growth” meme. It’s the characters growing and the audience growing with them over time. What should people take away from Insecure when those credits roll for the final time?
I would love for people to walk away knowing they saw Black life existing in a very normal way, with a kind of humanity. Seeing our lives with love, beauty, and normalcy, which we tried to do at a very high level and inspire the people behind us. Kind of like how I felt being inspired by The Cosby Show or A Different World, where I felt like, “Wow, that’s my life. That’s my existence up there.” So for somebody else to be inspired by our show for the same reasons, that’s amazing.
I just want people to always feel like Insecure is a special part of their lives. We got to do some things that were groundbreaking and we opened a ton of doors for Black creatives that just weren’t there when I started on the show. I remember what it was like being the only Black writer in different writers’ rooms for seven years, so the fact that the writers in my world won’t know that story—at least right now—is so great. The fact that Issa will never know what it’s like to be the only Black writer in a room is amazing; she skipped all those years. And that’s kind of the point: People like Rosa Parks paved the way for us, we’re paving the way for other people.
Running a show is a management role. What did you learn from Mara Brock Akil during the Girlfriends era about leadership and how have you applied that on other shows where you’ve had leadership roles?
I got to learn from one of the best to ever do it. Every day was like watching a masterclass in seeing someone work, break shows, and how to treat people. Eighty percent of what I still do, I learned from Mara. She set such a great precedent for how I treat people, how I work, how I think about stories, and she was doing things on Girlfriends that we kind of do now. Girlfriends always played with tone and comedy. She always shot it like a single-cam show. She would end episodes on moments that were kind of sad. She always had great music. Then there was the fashion. And she was doing these things in ‘06 that we kind of take for granted now. I’ve learned from being on other shows too, but because I didn’t know anything at the time, working with her for four years was the most knowledge that I soaked up.
I’m not pollyannaish about the current state of Black art. I knew at the time that a lot of people’s post-George Floyd diversity pledges were bullshit because I remember what happened to Black TV moving into the 2000s, back when you were just getting into the business. How do you feel about the state of Black art right now, coming off of five seasons of Insecure? Are you at all optimistic about the future?
I agree with you. People say, “Oh, it looks like we’re having a Renaissance” and I’ve seen like, four Black Renaissances [laughs]. The problem with a Renaissance is that it has an end date. I don’t want there to be an end date for any people of color trying to tell stories, I want to continue to the point that it’s just the norm.
Now is the landscape better than it was when I arrived? Hell yeah. And I think the rise of the streamers really gave birth to not having to tell stories for the masses like the networks have to do because they’re trying to appeal to advertisers and get the biggest numbers they can, whereas streamers are working off of subscribers and it benefits their financial model to serve all people. When we started, Black-ish was just getting on the air and now there’s like three ish shows. The landscape is dramatically better than it was when there was just one.
What’s also better is that there are so many Black showrunners in deals and “overalls” now; that just wasn’t poppin’ six years ago and that’s so dope. I think we have a long way to go in terms of shows run by white showrunners to have diverse writers’ rooms, directors, and cinematographers, because there’s no promotion in me giving another Black person an opportunity on my show. That’s very one-to-one growth, of course it’s gonna happen. But the real growth occurs on 80-something percent of the other shows that are primarily run by white people. I got so many jobs just off one recommendation from one white showrunner to another white showrunner because they just trust each other more inherently than they will any people of color. I just know that sometimes that’s how you get jobs: “They were great, you should hire them.” That’s how it happens and that’s where I feel like the real growth still needs to occur: over there.