'Insecure' Boss on Pushing the Boundaries in Season 2 and Surprise Premiere Twist

Showrunner Prentice Penny talks to THR about season two's "creative challenges" and Issa and Lawrence's big moment.
Justina Mintz/Courtesy of HBO

[Warning: This story contains spoilers from Sunday's season two premiere of Insecure, "Hella Great."]

After a critically acclaimed first season last fall, Issa Rae's HBO comedy Insecure returned ahead of schedule for its second season Sunday.

Picking up three months after the season one finale, the season opener saw Issa struggling to come to terms with her breakup from longtime beau Lawrence (Jay Ellis). While Lawrence has seemingly already moved on to someone new, the premiere opened with a montage of Issa's bad dates  which provided a perfect opening for one of Rae's raps and a daydream sequence, two signatures of the HBO comedy. (Despite their split, the episode ended with Issa and Lawrence hooking up when he came to her apartment to pick up his mail.)

But while Issa was consumed with romantic troubles, Issa's best friend Molly (Yvonne Orji) was focused on work, particularly when she learned she was making less than one of her white male equals at her law firm.

To break down the premiere and the rest of season two, THR spoke with showrunner Prentice Penny about where Issa and Lawrence go from here, the inspiration behind Molly's storyline and the one downfall of landing a coveted post-Game of Thrones timeslot.

What were your and Issa's big goals going into season two?

Our first thing was, where do we pick these people up? Where's an interesting place to pick them up? Are we picking them up a week later, a month later, a year later? Because we were kind of free to do whatever we thought. As we kept talking about the characters, [we thought] they just broke up and what does it feel like when you break up with somebody? We kept talking about when you break up with somebody and the process you go through. For us, as we thought about things that felt organic and things that happened to friends of ours, we settled on this three-month time. Because three months is a good amount of time when you've broken up with somebody that you kind of have to start making a choice: Am I trying to get back with them? Am I moving on? Certainly, it's a fair amount of time when people have heard enough of your lamenting for that person and they're kind of over it. So it's this time when you're supposed to seem like you're doing better but if you're not, what does that look like?

Then we started talking about, in general, the idea that what people present publicly in their lives is different than what they actually are feeling privately. Those ideas started to take over, not just the breakup, but things that our characters are experiencing in their own lives and the idea of we have to put on a façade and wear different masks. That ended up being how we started to settle on this time and this idea that things are seemingly great, but really are you?

The show originally premiered as a fall show but HBO brought you back in July. How did that impact the writing and the production of the show, if at all?

When we came back, we initially were coming back for 10 episodes. I think we all thought we would be airing in the fall again and then HBO contacted us a few weeks into the writers' room and was like, "Hey, what do you guys think of airing with Game of Thrones?" We were like, "Uhhh… yeah." (Laughs.) But because we were coming on early, we had to have these hard production dates that we needed to hit. We usually have all [the episodes] written before we start shooting because I'm on set, Issa's acting full-time so we can't be in the room in the same way and have the same impact that we think the show needs to do well. We just said, "Can we just do eight [episodes] again?" And they were like, "Yeah, of course." That's the only way it impacted production.

What were some of the other unique challenges you faced in season two that you hadn't faced in season one?

I think in a lot of ways HBO helped us. Our show is a super heavy location-based show. Eighty percent of our show takes place on location so we just needed an extra day so they were very good. Last year we were five days, this year we were six so they were accommodating about letting us be out there more.

I think for us it was honestly about how do we push ourselves? How do we not get complacent and just repeat it? For our director Melina Matsoukas, she was like, "I want to keep pushing the boundaries of the way the show looks and sounds." Certainly, a show about color and certainly also a comedy  what can a quote unquote comedy look like? How far can we push it and make it feel interesting and real and organic? I think things like that became creative challenges.

What are some examples of how you pushed those boundaries in season two?

I think the whole look of the show just got really elevated and more nuanced. I think for us too, what Melina said of, "Can we push the boundaries?," I think that helped us story-wise say, "Can we push the boundaries?" We were playing with time more and the way we tell stories more. We have one episode that just takes place in one day which is kind of new for us. How do you take all these things that people experience and jam that into just 24 hours? Because obviously our show is a show where things sort of have to ruminate and then happen so that was challenging. We have another episode  I don't want to give anything away  that completely plays with time and the perspective of who the story is about changes constantly throughout the episode. You never know whose story this is. They're all kind of connected  Issa, Molly and Lawrence  you don't know whose story you're following until the end of it. I think the way we started to tell our narratives this year, I'm more excited about doing that if we get a season three.

The season premiere also introduces a big obstacle for Molly when she learns that one of her white male coworkers is making more money than her. What was the thinking behind this storyline?

My wife is a recent attorney; my mom is just short of a judge; I grew up around lots of black women attorneys so I was very familiar with what they experience in a corporate environment. Last year, Molly had a lot of dating stories because that was just her character but we felt that we didn't introduce enough about what it's like as a person of color who works in a very corporate environment. Lawrence works in a tech company, Issa works at a non-profit but nobody has a real corporate experience like Molly. So just so Molly isn't a woman who's dating all the time, she works in this environment so [we thought] what kinds of stories can we tell that will feel fresh and interesting? It just kind of organically started coming up. Our friends had experienced it, my wife had experienced it, my mom had experienced it, Issa's friend had experienced it. The universal truth is I think it's not indicative of just law, I think people of color typically… don't make as much as their white counterparts and that's white women included. So I think there's this thing of, "I'm doing the same amount of work if not more and I'm not valued the same way." For us, it was, "How do we tap into that and how do we make it a theme throughout the season?" I think even bigger than that, I think Molly's value this year is something that we're exploring, not just in her work life but also in her relationship life.

What can you say about that balance between her work life and her dating life beyond the season two premiere?

This is a character who obviously had a lot of issues and is going to therapy now and exploring that now. Our thinking was, "Is there a way for her work life to be intertwined with her romance life?" So for us, it was kind of fun because we kind of explored that balance with that character. Everything doesn't have to be so isolated in terms of, this is her life here, and this is her life here. Issa's life is very much like that. Last year, everything was really separate. I think sometimes in our lives things aren't so segregated like that. We just liked the idea of things starting to mish-mosh and things also starting to meld together.

You also have a character coming up in season two that is racist and specifically discusses Trump's proposition for a wall. Given everything that's happened since season one, how much did that impact the writing for season two? How did you decide how much to tackle that subject?

Obviously, the election was happening while we were getting ready to start the room back. First of all, we don't want to give any face time to him on our show. Some of these shows are going to haul that stuff in a much better way than we can, like John Oliver and all those shows can do that in a much better [way] because our show isn't about that. Our show is about this character who's in this world and obviously the world can be changing and so for us, again given that Trump is not really the narrative and the premise of our show, we thought, 'How do we talk about the climate or the way things are changing or what people are talking about, and demonstrating that without saying this is the person and this is the thing.' But obviously, people are a little less sensitive to other people and the world feels very divided right now. So for us, it was how do we include that feeling and that sentiment without being so specific. At the end of the day, it's not about that person, it's just about how people are now treating each other differently based off that. So it was like how do we talk about those things in a way that feels true to our show but we're not just doing a very special episode of Insecure?

The season premiere ends with Issa and Lawrence hooking up. What's going on in Lawrence's mind in that moment? What does this mean for them going forward?

It certainly sets things off in a way. (Laughs.) I think they haven't physically since each other since their fight in episode seven. They have a very small conversation in episode eight, but that's their only interaction post the big fight. So obviously he's called her to get his mail but they haven't ever talked. There's no closure, everything is still sort of fresh. I think he obviously still loves her and still cares for her and I think seeing her sets off something that even he wasn't expecting. I think Lawrence is feeling confusion: "I love her, but I shouldn't. I'm mad that I care about her"  all the conflicted things that he's feeling I think she's feeling too. Again, because they're not talking about anything. They're representing this face that they're OK or they're trying to be OK but neither one of them is saying, "Hey, I miss you. Hey, I'm sorry. Hey, I really love you." They're speaking words but they aren't actually communicating.

Obviously, Lawrence is still a central part of the show aside from his relationship with Issa so how much interaction will we see between the two of them as they're trying to figure out their feelings?

I don't want to give anything away but I think that even when they're not together, the undertone of their relationship is carrying throughout the season. So there are times you'll see them together, times you won't see them together but their presence is always impacting each other. The choices they make  again, because there's no real closure  the choices they make are impacted by each other. That's a constant and a very heavy presence even if they're not in scenes together because it just permeates all their choices and their decisions.

Insecure airs Sundays at 10:30 p.m. on HBO.

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