Insecure’s Showrunner on Issa and Molly, Condola’s Pregnancy, and Why Dro Isn’t the Worst

Photo: Courtesy of HBO

Visually and narratively, Insecure’s fourth season was the show’s strongest. Issa finally had a job she was passionate about, and she had worked through her issues with Lawrence. Molly was in love with Asian Bae Andrew, finally happy in a romantic relationship. (Kelli was, as usual, totally off the chain.) And then a finale bombshell: Lawrence’s ex-girlfriend Condola is pregnant and Lawrence is the father. The moment seemed to sink the episode — the season! — before Insecure returned to the relationship that’s always been at its center, the friendship between Molly and Issa.

Over the phone, on a break from Insecure’s recently convened season five writers’ room, showrunner and finale director Prentice Penny talked Vulture through the episode and its many relationships. It all comes back to Issa and Molly, though: “Molly and Issa have been friends since they were 18 years old, and now they’re in their 30s. This idea that you’re only going to have rosey moments the whole time is difficult,” Penny tells me. “When you’ve been friends for so long, you know where all the bodies are buried. You know all of their mistakes. Both Issa and Molly were taking that friendship for granted for a long time.” Prentice broke down the finale, that shocking pregnancy announcement, and what’s next for Issa in season five.

How did the writers’ room arrive at the idea to end season four with Condola’s pregnancy?
We’d felt like we had done a really good job — maybe even too good of a job — at leveling Lawrence up. If you remember in the season two finale, Issa has this fantasy of what her life with Lawrence could look like: She dreams of them being married and having a kid. We wanted to play with what happens if that fantasy gets altered. Is that something she could deal with? Happiness is a choice. That’s what Issa says. So we wanted to challenge that point of view. Can you find happiness here? Or can you not? There’s no wrong answer.

Was Lawrence’s fade a bait and switch?
His haircut? No! That was just Jay [Ellis] wanting to try something since we don’t see Lawrence for a second. People change their haircuts all the time. It wasn’t a fully thought-out thing. He just wanted to try a clean start.

Back to the pregnancy scene: What was the response during the table read?
We read the finale in a trailer, which is never the best place to read the script, because the fans are going. It also doesn’t read the same because the actors aren’t giving you the same emotion. The rehearsals, though, definitely gave a lot of chills. We didn’t want to waste the emotions there.

Tell me about rehearsing this scene.
We tried it in a lot of different ways. For one take, I might tell Jay, “Try to be very logical with her about why this doesn’t make sense.” In another take, it was, “Only think about what you’re losing in this scene. Don’t think about anything else. Don’t think about her feelings. Just think about your feelings and what you’re losing.” And just those two notes gave it a very different performance. Same with Issa and Lawrence. I would tell Issa [Rae], “Hey, this time, you can’t even look at him. Once he tells you, don’t even make eye contact with him, you’re just so hurt and disgusted.” In some cases, I would say, “All I want you to do is try to look in his eyes and read them. Just try to understand. Don’t break eye contact with him, just to try to find something in there to cling to.” You could hear a pin drop when we were filming those scenes. They were brutal.

The cuts between those two conversations were really dynamic. Why did you decide on editing it like that?
Originally, when we were writing it, it was more linear. It was a flashback. You would hear the news, watch the whole Condola-Lawrence scene play all the way through, and then cut back to Lawrence and Issa. It just didn’t feel as interesting. Spike Lee did a similar [intercutting] in Mo’ Better Blues, where Denzel is sleeping with two women and he’s having a conversation with both of them. That always stuck with me. And if we’re intercutting like that, I had to be very methodical about how I was going to shoot it for it to feel like one big conversation between three people.

I loved how beautiful the finale was. The color palettes and tones in every scene were just gorgeous.
When they’re looking for Tiffany, we shot it very differently than we shot the bookends of the episode. When they’re not looking for Tiffany and after they find her, we shot it in our much more traditional style. And then, when they were looking for Tiffany, we shot it all very docuseries.

Later, when Issa’s on the balcony, I really liked this idea of shooting her silhouette as she’s walking out, just doing things that we don’t normally do cinematically in our show. I was trying to go for a very American Honey feeling and vibe. And so I was really trying to lean into that again. We never shoot in slow motion, so that was something new that I wanted to incorporate. I was just really trying to continue to elevate the show visually to where the character was.

Back to the love triangle: Do you think Issa would stay with Lawrence if he chose not to be involved in the child’s life?
I don’t think she’d be with a man that would not actively be part of his child’s life. If he’s gonna ignore his child, I don’t think that’s a character trait she would want a partner to have. I just don’t think there’s a world where she would ever be okay with him doing that.

The city and culture of Los Angeles are obviously part of the fabric of this show. Could Insecure follow Lawrence to San Francisco?
Yeah. As long as the characters always tether back to Issa, it merits following them. That’s what we’re figuring out now in the writers’ room for season five: What does it look like if she’s commuting, or what does this look like if we’re in his point of view? Do we tie things back? Do we bring things full circle?

Do you think Condola still has feelings for Lawrence?
Yeah, of course I think she does. It’s like a volcano: It might not be active, but it doesn’t mean it’s not bubbling under the surface. One of the directions I gave Christina [Elmore] was, “When you’re saying the ‘you can be involved’ line, try one take where that’s the only moment you’re really vulnerable.” Christina plays Condola as very measured in how she responds to things, and obviously she’s had time to process this. At a certain point, she understands that this is hard for him and tries to appeal to him, too. Then she says, “I’m not trying to trap you,” and Jay gives a great look where he doesn’t believe her. That’s when she closes up again.

But yes. She’s going to maybe have a child with this guy, and they used to really care about each other. Those feelings are on the table for sure.

I’d like to talk about Molly and Andrew. Can you clarify how long they were actually dating in the show’s universe?
In the course of this season, the first five episodes are five months. The last five episodes are two months. So they were dating like seven or eight months, if you take it back to season three.

Do you think Andrew gave Molly too many chances?
Hmm. We talked a lot about that in the room. I don’t know if he gave her too many chances, but we definitely feel like he acquiesced a lot, and maybe he shouldn’t have. We’re always trying to write relationships where one person isn’t the cause of something. Two people are in a relationship. It takes both of them to make it continue, whether it’s a bad pattern or not.

Why do you think Molly was willing, eager even, to work things out with Andrew but not with Issa?
I don’t know if that’s true. Why would you think she was more willing to work things out with Andrew?

During their breakup scene, Molly keeps saying that they’ve been putting so much effort into their relationship. She’s making a clear argument for why that relationship is important to her. But with Issa, it seems like someone else — usually Andrew or her therapist — has to convince Molly that the friendship was even worth maintaining.
Right. But after what happened with Tiffany, you can see the looks that Issa and Molly share when they’re on the bus. Those things that Derek is talking about are resonating with both of them. After they find Tiffany, Molly realizes that the relationships she has are special and she wants to salvage them. Even her energy is different. She’s much more defensive in her first conversation with Andrew when they’re talking about his brother. When she comes back from looking for Tiffany, she’s just like, “I want to talk about this. I don’t want to just be defensive.” She’s willing to be open.

I think she takes that same energy to Issa. With everything post-Tiffany, she’s different. She’s the one that called Issa this time. In episode nine, if you remember, Issa was the one that called Molly. Now Molly’s tried with Andrew. Maybe it works out, maybe it doesn’t. And she tried with Issa. Issa and Molly have a different history, but Molly is making an effort on both sides.

When do you think Molly and Issa’s friendship was at its healthiest?
It ebbs and flows. The end of season three, they have a little bit of a run about Nathan, but it’s not a real issue in their story, really. I feel like friendship is good. I really don’t like when people are like, “This is a toxic person!” People don’t cancel real people in their lives like that. I’d be curious to ask everyone that tweets “cancel Molly,” if y’all cancel people in your lives like that? People that you’ve been friends with for 20 years? Like, stop it. I think people want these characters to make better decisions. But people are with people that cheat on them, people are with people who are horrible to them, people don’t cancel their mom, their dad. People don’t cancel people like this in real life, the way they say they cancel them on Twitter!

Speaking of Twitter: After Andrew mentioned having difficulties with his sister in two separate episodes, I saw a fan theory that his sister was actually LaToya. What do you make of that?
Oh, no! I will tell you LaToya is a black woman and Andrew is Chinese. So no, I don’t even know how you would get there at all. [Laughs.]

I also wondered if you saw Vulture’s ranking of the men on Insecure.
Is that the one that had Thug Yoda ranked as No. 1?

What was the ranking criteria? What was it based on? Was it based on personality, or looks, or —

It was based on personality and how they behaved in their personal relationships, mostly with either Issa or Molly. What I’m really asking is if you think Dro should be last.
Oh, I don’t think Dro should be last at all! I think people sometimes can’t separate Sarunas [Jackson, who played Dro] from Dro the character. [Editor’s note: I could separate them, actually, because his baby isn’t my business.] This is just my personal opinion. I think people know a lot about his personal life. What people understand about him and Dominique [Perry, who played Lawrence’s season two fling Tasha] being co-parents overlapped over at a weird time with the character.

Molly is a grown-up. Dro was married. He always said, “Hey, this is the scenario. You know what it is.” And he wasn’t ever lying, trying to make it not be that. Molly’s the one that called him and went back to him. Now you could say when Dro was tripping about the house key, yeah, that’s an offense. I feel like he was honest. He was open. I think people don’t necessarily like that Molly got her heart broken, but I don’t know anything he did that was that egregious. I just don’t know why he would be last. He is married, his marriage had an agreement, and Molly knowingly engaged in that. Why did you rank him last?

I agree that Molly knew what kind of relationship she was entering into. But time and time again, Dro would tease her with very relationship-y things — running her a bath, having meals together, all these date activities — but he wouldn’t want to engage unless it was on his terms. 
I get that. But I also think Molly has her own agency. Molly can say, “Don’t do that.” We could’ve written that scene differently in hindsight, but yeah, that was part of it. The other thing to remember is that they were friends from back in the day. In real life, I could see a guy like that doing those things because she’s his friend. It’s not just like some girl I met in a bar and we just have this sort of hookup and my wife is cool with us dating. I think if Dro looked back on it, he would say, “Yeah, that probably was not the move to do that with my friend,” or “Hey, I might’ve said the wrong thing.” I don’t think that inherently makes him trash or last on the list, but those are fair points.

I love that you put Thug Yoda as No. 1. Reading it, I was like, Whooo is going to be No. 1? I was really curious. I thought that Derek was going to be higher. What was Derek, like number six?

He was seventh. I love Derek, but he really lost me when he said having a daughter made him rethink how he’s treated women. It shouldn’t take having a daughter to do that.
Yeah, I get it. That’s not great. But that’s real for a lot of men!

Insecure’s Showrunner on That Surprise Finale Pregnancy