Last night was the season four finale of HBO’s hit series Insecure, which was written and directed by its showrunner Prentice Penny. With the show already renewed for another season, audience didn’t know what to expect. With Issa and Lawrence starting to get back together, since episode 8, it was a question of whether this happiness was too good to be true. Then there’s the rocky relationship between Issa and Molly and Molly and Andrew. Molly has had a lot to deal with and audiences have been divided as to whether or not to be on her side of things.
Shortly after the episode aired, Blackfilm.com spoke exclusively with Penny on the final episode and how several plot lines played out this season.
When did you come up with the season finale episode when you wrote it?
Prentice Penny: We came up with it into mid-season in the room. We were always just trying to find ways to dirty out Lawrence’s character a little bit. That’s real life. The whole purpose of the season was, “Are these relationships for a reason or a season?” These characters are 30-31 and they’re entering a new phase of adulthood. Who’s supposed to be around for a reason and who’s supposed to be around for a season and who’s here for a lifetime? We wanted to explore “Is Lawrence a reason or is he a season?” “Is Molly a reason, season or a lifetime?” Same thing for Molly. She says at the end of episode nine, “Maybe who you are now and who I am now just don’t fit anymore.” That’s a real question. We always knew that theme was going to be playing this year. Was Issa and Molly’s friendship building to something? With Lawrence, “What is the Issa and Lawrence version of that?” of the Molly situation? That’s the idea that we landed on and that we wanted to explore.
With Episode 8 when Lawrence and Issa got together and Condola calling him throughout the episode, it almost became a little predictable where things were headed; especially when there are two episodes left to go. With Nathan featured in episode 9, things got intriguing. Was the game plan to shift the focus off Lawrence and see whether Issa would wreck a good thing happening?
Prentice Penny: It’s so funny because we always knew that if we had Condola calling him a lot, it wasn’t until hindsight that we said, “Oh, people might read that as ‘she’s pregnant.'” But in our world, we never wanted her to know she was pregnant at that moment. We were always like, “she was just trying to get back with him.” It really was in between episodes 9 and 10 when she discovered she was pregnant. Not when she was calling him. Weirdly, if you look at it, it looks that way but when we were breaking the story, we never thought about it like that. We were always like, she just trying to get back with him because we were using that as a plot device for Issa to activate Issa. In hindsight, it probably will read that way. But that wasn’t our intention.
Throughout the season, Molly’s had this hate towards her from fans based on her actions, whether it’s with Issa or with Andrew. How challenging was it defining her character for this season?
Prentice Penny: I think it’s a testament to the Yvonne’s acting. The funny thing is that they’ve never been undivided. They’ve never been on split sides. The most thing they’ve had is a little bit of argument about Nathan, a little bit of argument about Lawrence. Molly has to run interference for Daniel and Lawrence in the first season, but they’ve never really had issues. We really wanted to explore that. The audience never had to like pick a side. The audience never had to a choose a team, like Team Daniel or Team Lawrence or any guy team.
You never questioned if Issa and Molly are on the same side. So this was the first season where that happened. I think just because naturally the show is through Issa’s point of view, we probably underestimated that in some capacity in the writers room that the audience will naturally default to Issa because it’s her show. I think we underestimated that. But we always tried to write it from the standpoint that both had receipts on each other. Then it was a 5-050 split. But in hindsight, we’ve talked about how we maybe should have made Issa a little bit harsher so you empathize a little bit more with Molly as opposed to painting it down the middle.
I think in some ways people are actually more Molly than what they care to admit and sometimes that’s the hardest thing to say. When you watch the show you want to identify with the best parts of the show, and not say to yourself that you might be the worst part of that show. That’s what people are actually are reacting to. With Molly they might be seeing parts of themselves, but they’re not consciously aware of it. We always said in the room that Molly’s been a great friend to Issa from day one. When Issa needs to go to Nathan’s house because he’s been ghosting her, Molly’s there. Molly goes with her when Issa has to do the Lyft in the season two premiere. Molly’s running interference for her and Daniel and Lawrence. She’s there for her when they break up. Molly’s always there. She’s given her money and so I was really surprised that people turned up so quick on Molly this season. To me, Molly has been a way better friend to Issa than Issa has been to Molly, but that’s in the eyes of the beholder.
This season seemed to be more centered on the four characters, Issa, Molly, Lawrence and Andrew than in previous years where, you never really gave much to Molly’s boyfriend’s. Was there a conscious effort to make them a bigger part of this season?
Prentice Penny: I think it was. That was something that we wanted to explore. Explore that dynamic. We always have three points of views in our show. We always have Issa’s point of view, Molly’s point of view, and always had a male point of view. Typically, it’s been Lawrence and in some moment it’s been Daniel. And there’s a couple moments it’s been Nathan and I think around the time of the episode, there wasn’t really a male point of view. Specifically, around episodes 5,6, and 7 there really wasn’t a male point of view in the show.
Our thing was to explore Andrew and round that character out in all of its fullness so that we could explore somebody. With the show, it’s always tough because you never want to get too far off because Issa is the sun of the universe. We didn’t want to venture off too much. We need to be close to home. But obviously, because it’s Molly that gave us some other territory to explore. That was definitely a calculated thing to explore this year.
For the final episode this season, you were able to use Tiffany postpardum to bring in the whole cast. Can you talk about that?
Prentice Penny: The original premise was to tie it back to “Looking for Latoya.” We’ve never really integrated the show within the show as a shooting style, nor as a story device in the show, and we felt this year that that was an interesting way that we could explore the way that they don’t really look for black women in the same way that the healthcare industry doesn’t really look for black women when postpartum are there. We set it for Tiffany when she says in episode four, she says the doctors didn’t really believe she was in as much pain as she was. Because doctors typically don’t believe black women don’t have as much pain as white women. We wanted to tee up the idea of what Serena Williams went through. We were teeing it up in that episode to pay it off in this episode. It felt like a natural idea to explore Tiffany’s thing in the premise of ‘Looking for Latoya.’
The original cuts of the episodes the script started with a lot of chaos when you see the, when you see Natasha and all the friends arguing outside the bus. That was actually the code open originally, that chaotic scene and you don’t really know why you’re watching this moment. Then when Derek was sort of telling the girls what was happening with Tiffany, we shot reenactments of what Tiffany was doing with like a fake Tiffany. We really leaned into the ‘Looking for Latoya’ model as a device to pay back in the edit. In the cut, it didn’t feel like our show. But that was always the intention, to tie in Looking for Latoya with Looking for Tiffany.
Are you involved with the Looking for Latoya podcast?
Prentice Penny: Of course, one of our writers Amy Aniobi really spearheaded that and she’s one of our EPs and has been with the show from the beginning. We were really excited that we got to branch that out into a bigger thing. Every year we tried to expand on that, the show within the show. We’re having some conversations this year, but the show within a show really happens organically. In the writers room, it’s never anything that we manufacturer or force. It just happens organically. Looking for Latoya came out of the thing where we were watching all these podcasts about like serials, and HBO did the live version of what serial was on and all these docuseries, like Tiger King and others. All these docuseries around murders and things felt like the right territory right now. This is something that was discussed in the writers room and what would it be like for us? We’re a comedy show, but we’re also trying to point out similarities on what’s happening in the real world.
Where do you go next year? Have you started working on it? Have we seen the last of Lawrence or Nathan?
Prentice Penny: We’re starting to but you can’t say that with our show. You never know if Daniel pop up. When they’re going to pop up or how they are going to pop up. We’re in the middle of writing the first two to three episodes and I’m super excited about where season five is going. We’re building on what we just finished like and I’m super excited.
Congratulations on this year. You had Uncorked and this episode. Are you going to direct any more episodes for next year?
Prentice Penny: For sure. I usually just have a direct one. We are trying to give spots to other directors but usually as the showrunner, there’s so much I have to do that I just don’t have the bandwidth to do more than one because either I’m editing or casting or rewriting or supervising on set. Typically one episode, at least for our show, is about as much as I could handle in terms of responsibilities. That was great about coming from Uncorked and coming back to do the finale. I got to take other ideas and things I learned and apply them. If you look at the moments when we’re in the normal parts of the show, you saw a standard way but when we were shooting Looking for Latoya, we specifically shot it docuseries style. We would do more like the way The Office was shot where you’re wit panning between characters and not cutting. I really wanted to lean into a different cinematic style. But that was all because I was able to do more stuff from the movie side and incorporate those ideas and things into the into the finale.
Before I let you go, can you talk about the tribute to Nipsey Hussle and Kobe Bryant?
Prentice Penny: Absolutely. Nipsey Hussle was always as a part of that. With Kobe, we wrapped before before he passed away, but we shot that after. We had the Nipsey shot and we were like, “Oh, we need to do something for Kobe.” We were still editing this episode up until a month ago. With Kobe passing in January we wanted to honor Nipsey and Kobe as LA icons. It worked out that we were able do that and we’re very obviously heartbroken but honored that we were able to put the two of them together in the finale.
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