Final seasons are never easy to do well, as the history of television is packed with entries that left fans disappointed. It’s something Insecure showrunner Prentice Penny was conscious of when speaking to Collider via phone, as the critically acclaimed hilariously awkward comedy will be wrapping up with Season 5 this fall. “People are going to see our finale and they’re going to say, ‘I hate it’ or ‘I love it.’ And everything in between,” he said.
While Penny didn’t spoil anything about the final adventures of Issa (Issa Rae, who co-created the series with Larry Wilmore), Molly (Yvonne Orji), and their friends, he did discuss what shows the writers looked at as examples of great series finales and what was important for them to capture with the Insecure finale. He also dished on one of the abandoned ideas they had for a finale that actually made it to the scripting phase, until they realized that maybe a drunken Moroccan adventure wouldn’t be a great idea.
[Editor’s note: The following contains spoilers for Insecure, Season 5, Episode 2, “”Growth, Okay?!”]
Collider: To start off, I know that Issa’s talked about how this was always intended to be the final season. From your perspective, when did that really start feeling like a reality?
PRENTICE PENNY: I think when Issa and I started talking about the last season last year. We always get together before we sit with the writers to talk about, what do we want to talk about this season? What do we want the show to be? I want to say it was around April when it was like, this is really the last time we would do this. I think that’s when I felt it for the first time. I was like, oh, wow, this is the end.
When you talk about the end, what are your favorite kinds of endings? What feels like a good ending to you?
PENNY: I always like when I feel like, one, I watched it for a reason. I hate feeling like, what did I just spend the last six years of my life invested for? So I think that — well, what’s my takeaway from it? I think the other thing that I like is when I feel like the character’s journey feels complete. And that needed to happen.
Those are the two things that I think about that matter to me the most. It doesn’t have to be happy. It doesn’t have to be any of that. I love the Breaking Bad finale. It doesn’t end with Walter walking off into the sunset. I love that the character redeemed himself in some way and got what he, I hate saying deserved, but he lived a life that he felt, “that was the life I needed to do and I needed to do one last thing and save Jesse.” That’s commendable.
I just think those are things that matter to me as finales. It’s tough, too. It’s so tough because there’s so much pressure on it anyway. The first episode of a show and the last episode have the most pressure on it. You’re never going to do everything anybody wants. People are going to see our finale and they’re going to say, “I hate it” or “I love it.” And everything in between. What we just felt was, did we finish the character’s journey? And that’s where we wanted to end it. I feel like we did that.
That’s great. If you had gone on to a Season 6, do you feel like there were things that you would have wanted to continue to explore?
PENNY: I don’t know. We didn’t, so it’s tough to say. I don’t feel there are enough stories that we had left to tell that would require a whole season. I don’t think that. I think we could have found stories and found interesting things to talk about. I think the things that we would’ve wanted to do had we done it was we always talked about, it’d be interesting to do a Kelly episode or a this episode.
I don’t know if all of that warrants or needed to facilitate an entire season. I feel like we told the character’s journey in a way that felt good. Again, maybe there were two or three things, but I don’t think anything that’s like, we could have done a whole season around that, or that would have been an interesting thing. I think we feel that this feels right. I don’t feel like there’s anything we left on the bone to really say, oh man, that never got explored in a way that would have been really interesting.
When it comes to telling the end of a coming of age story, what are the details that you feel need to be there?
PENNY: Coming of age?
Well, I said coming of age, I don’t know. You probably have a better term for it than I do, because coming of age does imply teenagers.
PENNY: No, I’m agreeing with you. I think that’s actually the perfect thing. This is a weird tangent on this, but my wife and I were talking yesterday — she was telling me about a friend of hers who had a son who was 17. She was saying that when he started high school, he was a typical boy. Doesn’t really want to help around the house that much. You got to remind him 50 times. And she was like, he’s a senior now, and he’ll just do things that I don’t have to tell him anymore. He’ll just do them voluntarily, asking “How can I help do this?” And I was like, that’s coming of age. It’s recognizing, going from thinking about yourself to thinking about others.
I think that’s similar for the characters in Issa. It’s like she’s starting in a place that’s very insecure, and certainly wanting her insecurities to be over with at some point. I think the place we always wanted to grow her was that your insecurities never leave. You just learn that they’re always a part of you and for better or for worse, and that you find ways to deal with them. Either embrace them, or have the tools to understand what they mean. That’s where we wanted to get the character.
So it is a real coming of age. I think anytime you’re growing in some sort of capacity, it’s all a coming of age no matter the physical age, because you may not learn a lesson until you’re in your 50s. I think that’s the point it was for us, was that we wanted to let her character … her character felt, “This will always be with me. I just have to learn how I deal with it in a way that’s productive and not destructive.” Then that’s the journey. That’s where I feel like we eventually get her.
This would be a better question to ask you after watching the series finale, but I feel like with final seasons there’s a lot of pressure to end the show with a big life event — a big wedding, or someone has a baby. Were discussions around those elements a big factor in the writing?
PENNY: There were absolutely factors in that we felt that what we wanted to do was, when you start the series, Issa’s going from 28 to 29. All the characters are single, but dating. In the pilot, Molly’s just gotten broken up with, kind of. So for us, it was really about, that’s the end of one decade. So when we were ending the series, it was a lot of pressure on, well, what is the ending? What do we want to get them to?
We had actually written one or two different finales. They just didn’t really feel right. One of our writers, Amy Aniobi, was like, look, these characters lives aren’t ending. It’s just, we’re not going to follow them anymore. If we were writing season six, what would be interesting starting places for them? That really freed us up to say, well, what would be interesting starting places for all of these characters in some way? Then we just wrote to that and said, well this would be the things. What would we want to be starting these people with? That’s where we ended them.
I’m wildly curious. Can you say anything about what those other potential finales were like?
PENNY: One was, because it’s so far left, but we wanted to tie back in Morocco. Obviously in Season 2, they wanted to go to Morocco but they just do it in their house. What we wanted to do, we had Issa and Molly in Morocco in a Hangover situation where they were trying to get … It was for a bachelorette party. We were like, nah, this isn’t right. But it was basically them going to Morocco finally and they got stranded and they had to go from one city to Marrakesh in two hours. It was the craziest thing. It was like our Planes, Trains, and Automobiles, but we were like, it’s camels, taxis, and such and suches. They were on camels. It was crazy. They were going to end up seeing a Rihanna impersonator called Ribabba, who is a real person. It was funny, but it was crazy times. And we were like, nah, we can’t end the show with them on camels. So we punted on that idea for sure.
That sounds like an amazing episode, but I can totally see why you weren’t sure that that would be a great finale.
PENNY: There’s a full script about it, but it will never be seen. It just didn’t feel like our show. So we scrapped that and said, we’ll start over.
You talked a little bit already about Breaking Bad. Were there other serious finales that you looked to as inspiration?
PENNY: Yeah. Six Feet Under was a big one we talked about in the room a lot. By the way they played the time, by the way that they incorporated their natural storytelling device about their own characters. Typically they would do that for the people who were passing away. For them to do it for their own characters like a fresh way to invert it and still stay within the tone of the show. So Six Feet Under was a good one we would mention a lot, too.
You do have a time jump in Episode 2 this season. Is that the first of more, or is that going to be as far as it goes?
PENNY: No. We pop forward in time. We go back in time. We play with alternate timelines. We’re doing a lot of things about time this year. One of the things Issa and I talked about in the room a lot was, the tough part about life is that when you make a choice, you never get to see the other version of your choice that it could have been. You never get to say, well I made this choice, but if I had made that other choice, what would that have yielded? So we wanted to play a lot with time to let characters … I don’t want to give too much away, but we just tried to play a lot with time. It’s not the first time. We play with time in really specific ways for specific characters.
Looking forward, I saw that you’ve got a number of things lined up, including a fair number of things with HBO. What about HBO has felt like the right place for these things? What makes HBO special?
PENNY: I think what made HBO special is their history of shows that people love and people fall in love with. When I had my time there, I’ve left and I’m at Disney now, but what I have always loved about them is that they’re super creative, friendly-first and artist-friendly first, and it’s all about serving the story. Sometimes in other places it can be a lot of chefs in the kitchen, a lot of people with an agenda that isn’t about serving the show. It could be about serving that production company or serving that studio or serving that network or serving that executive. None of that is what HBO is about. They’re all about, how do we try to hit a bullseye every time? And they’re just always about that. At least, that has been my experience.
You have that level of, they just trust you. Amy Gravitt and Casey Bloyd have always been, whatever you guys feel is right. And then they’ll weigh in. Of course, they’ll weigh in with amazing thoughts, but it’s all about how to make the story better. You feel like you’re in a partnership, not an executive telling you, do this or else. It’s all about a conversation. When we get notes, it’s a conversation, “Hey, this thing, we weren’t sure about this. What were you guys thinking when you did this?” Because sometimes in the writer’s room we might know something, but maybe it’s not being translated fully that way on the page. Sometimes just having the conversation with them because they’re reading it for the first time the way the audience will watch it for the first time. And so sometimes they’ll be like, well that’s not maybe as clear. Maybe there’s a way to make that more clear. And you go, yeah, I could see that.
Even doing Pause with Sam Jay, it’s been the same thing. It’s a lot of trust. I think that’s what makes it so different in a million other places. It’s just trust in the creators to do it. And I think that’s a testament about who they decide to get in bed with, too. You don’t have to micromanage people if you trust your talent.
Meanwhile, I remember seeing those sizzle reels that HBO would do 20 years ago, and it would be all white men and maybe one white woman if they included Sex in the City. I love the fact that it’s such a different playing field now.
PENNY: I don’t think that’s just indicative of there. I think that’s all streamers, all platforms, all networks. I think it’s recognizing that we want to create. People want to see art that looks like themselves. Some networks have even farther to go than others. But I think that’s a testament to the landscape that we live in now. You can see that … shows that are … the streamers in that platform has allowed for more voices of color to create more art with them in mind. So you have shows like On My Block, or shows like Atlanta.
That just gives a platform to see other voices. They don’t have to appeal like a network show does to such a big audience. They can go, we’re going to hit a very niche market for this subscriber base because that’s going overlooked in other places. I think that’s what’s so great.
To wrap up — looking back, if you’re taking away one memory from the experience of making Insecure, one thing that really encapsulated the whole experience of it, what would you pick?
PENNY: I would pick, honestly, every day in the writer’s room. Just to be able to give and help in some small part with opening doors for other writers of color and directors of color. For us to talk about these nuanced stories that were going on in our lives every day with Issa and all of the writers was just such a … So much of what we would pitch would literally end up in these character’s mouths. So just to think about the origin of that to the screen of that was just really special. There was never a day that I didn’t look forward to being with all of them. The show wouldn’t be the show without them being such a gigantic part of it. And any success.
Those are my favorite, favorite, favorite memories because I helped get to shape a different landscape than I always saw in other writers’ rooms. That is the thing that I’ll always remember in those days, for sure.
New episodes of Insecure Season 5 air Sundays at 10 pm on HBO.
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