Insecure Showrunner Prentice Penny talks to Awards Daily about the journey from Season 1 to Season 4, what’s in store for Season 5, and how Lawrence figures into Issa’s journey.
Insecure had a bang-up year for Season 4, with the show confronting conflict between besties Issa (Issa Rae) and Molly (Yvonne Orji). This on-screen dynamic translated to a record eight Emmy nominations for the series in 2020, including Outstanding Comedy Series, Outstanding Lead Actress in a Comedy (Rae), and Outstanding Supporting Actress in a Comedy (Orji).
Prentice Penny has been an executive producer on the HBO comedy series since the beginning, so naturally he was especially thrilled (and surprised!) to learn that the show earned its biggest nomination haul to date, including his first nom. From Scrubs to Happy Endings to Brooklyn Nine-Nine, Penny has been a part of some of TV’s most memorable series of the last 15 years, and I asked him how it feels to be recognized for his work on Insecure after four seasons, and what makes this one stand out from the rest.
Awards Daily: Congratulations on your first Emmy nomination. What was it like finding out on Emmy morning?
Prentice Penny: It was super exciting. We hadn’t been nominated before, so I was a little hesitant to get my hopes up. You’re hopeful, but you don’t want to be disappointed. I was obviously hopeful for Issa and the rest of our cast and crew. I had just come out of the shower and I was watching on my iPad. I didn’t want to look, but my wife was looking, and I almost just missed it. I got to see it as I was coming out of the shower. I was trying not to see it but also see it. (Laughs) It was super exciting.
AD: What is it about this season that really resonated with fans? This season really seemed to strike a nerve with everyone. It was trending on Twitter every Sunday I feel like and just seemed to be like what everyone was talking about. What is it about this season that you think especially resonated with fans and the Television Academy?
PP: Like any show, you try to find your legs. We’ve been very blessed that our fans are super vocal on social media. I think it was a combination of a lot of things. We’ve never challenged the infrastructure of our show before, which obviously you had to have some currency in the bank of other seasons to do that. This season makes you really look at [Issa and Molly’s] friendship. I think based on where they were in their friendship, it got to the root. We’ve always rooted for them as friends, but to see that that friendship could be fractured really hit a nerve with people who really loved the show. I think it allowed us to do more deep diving on these characters and continue to open their worlds up in a different way. I think we found our stride even more so from directors and the writing. Also at the same time, people are stuck at home and it’s not the best circumstance from a health perspective and from a civil unrest perspective. I think people wanted to be entertained. I think people wanted to find something beautiful, especially with black people. Black people wanted to see something about our beauty and not our trauma. I think a lot of those things resonated at a very similar time.
AD: Yeah, also watching it during a pandemic, it was my comfort food to see people out and about. There’s a block party! Are you Team Issa or Team Molly? Do you have an opinion of who was in the wrong?
PP: I don’t have an opinion. I think one, we probably underestimated how much people probably would side with Issa, just because she’s the main character in the show, and she’s a character that wears more of her vulnerability on her sleeve than Molly. Molly is much more guarded and is a much harder character to pull for. From our mind, in the writers’ room, we always felt like Issa had made just as many indiscretions to their friendship as Molly, if not more. We tried to make it 50/50. We probably should have made it more 50/40. Inherently people will respond to Issa because she’s the main person. I was more Team “Fix the Friendship” more so than anything else.
AD: I think we all were. Although I like the fact that it feels very real, that some friendships outgrow each other. Did you always want there to be this bigger conflict between Issa and Molly? I feel like this has been building since Season 1.
PP: We were very careful that we didn’t want the girls to ever be frenemies. There’s enough content with black women tearing each other down on reality shows; that was never the purpose of this: It was about black women who love each other, which is the core love story in the show. The love story is their friendship. I don’t know if we felt it was anything that we felt we wanted to get to, but I think it was something that after Issa and I would meet before the writers’ room—back when you could still get together—we would spend a day just talking about our friendships and our friends and things we’re going through and themes, and based on where the characters had been, with the characters pivoting into their 30s, they’d be asking themselves, is this a thing I’m carrying for a reason, a season or a lifetime? We wanted to address that with Issa and Molly. They’ve been friends since they were 17 or 18 years old, but is this a friendship they can grow into adulthood with? We all know, like a snakeskin, there are relationships you have to shed, because they no longer serve where you’re going. We wanted to explore that with all of our characters. Issa and Lawrence, Molly and Andrew, Issa and Molly, all the four girls. It was definitely something that we felt was building that we wanted to explore. And we also were asking ourselves, what if we put that central relationship in conflict? What does that do for the show? It just felt like the right time to do it.
AD: It’s interesting that you brought up Lawrence, too. Every time I think we’ve seen the last of him, he keeps coming back. It makes me wonder if the journey is between Issa and her relationships or is it a romantic comedy where we’re following the journey of Lawrence and Issa? Why does Lawrence keep coming back? I’m not complaining! I love Lawrence. Just wondering.
PP: We never view this show as about Issa and Lawrence. That’s a story you have the most bank in because of their history and their dynamic. That’s actually one of the things we’re exploring in Season 5—why Lawrence continues to pop up in her life? Is that something she’s allowing to happen or is that something that she outgrew, too? All of these things we set up, we know how we want to pay them off. Your question is one of the questions we’re starting to get to in Season 5 that we’re really excited about. We feel this season is getting to the underbelly of self. The show’s called Insecure, so the way we approach the show is like a video game. Every level you have a new bad guy you have to defeat to get to the next level. This season is the next bad guy you have to beat, and sometimes it’s yourself. Sometimes it’s external things. That’s what we’re really getting at this season. What is the root of all of their insecurities? Where does it initially stem from? That’s really exciting to explore. The origin of insecurities. That’s what it really takes to go to the next place of being in a better place.
AD: You directed the season finale, which was so fantastic and devastating, even for the supporting characters like Tiffany. I think it’s interesting that Tiffany suffers from postpartum depression post-pregnancy in the episode, just as Condola decides to have a baby with someone she’s no longer with. Do these two threads comment on each other in any kind of way?
PP: No, but that’s an interesting vantage point to have about it. We were sort of just taking it from an interesting story perspective. What happens when life doesn’t give you things the way you thought it should look? What do you do? Sometimes part of being a grownup is saying, I thought it was going to look like this, but it looks like that, but you got what you want—does it have to be a certain way? It doesn’t stem from that, but I love that connection between those two things.
AD: I talked to you around the time the show first premiered back in 2016. It feels like such a journey for these characters. How do you think the show has evolved from Season 1 to Season 4?
PP: That’s a great question. I’m not sure what the show has evolved into, but it’s obviously evolved in directing, storytelling, and acting—it continues to get better every season. I feel like the show continues to push and ask uncomfortable questions and examines things in a different way. Season 1, we would have taken a much more narrative approach to certain things. As the show continues on, we start to ask different questions of ourselves. Sometimes episodes become very conceptual. As the show continues to evolve, we continue to get to the truth in a much more dynamic and interesting way. We’ve always wanted to get the truth, but how we get there now is much more dynamic and interesting for sure.
Seasons 1 through 4 of Insecure are available on HBOMaxx.