‘Insecure’ Series Finale: Issa Rae on Fate of Issa, Molly, Lawrence

SPOILER ALERT: This story includes spoilers from “Everything Gonna Be, Okay?”, the series finale of HBO’s “Insecure.”

With one final time-traveling episode, Issa Rae’s journey with “Insecure,” the hit HBO comedy that vaulted Rae onto Hollywood’s A-list, has come to a close after five seasons.

“Hopefully this finale is a late Christmas gift, an early Kwanzaa gift,” Rae told Reporter Door in a lengthy interview about the 41-minute episode, “Everything Gonna Be, Okay?” “I know people will have a lot to say, but I’m looking forward to not reading it.”

It’s been an emotional roller-coaster of a season — and a series — and Rae has been surprised by some of the audience’s responses. Asked what shocked her most about the reaction to Season 5, she says with a laugh, “The fans rejecting Nathan immediately. Kendrick [Sampson] is the best, and I love Nathan so much, but people were just not seeing it for Issa and Nathan.”

She was also surprised by the quick redemption for Molly. “Yvonne [Orji] laughs at it now and calls the audience very petty for accepting Molly almost immediately, but I’m really happy that people see it for their friendship,” Rae adds.

Rae reveals that key elements of the finale were up in the air until very late in the game, from the final decision on the show’s enduring love triangle to the brass tacks of the script itself. Although she and “Insecure” showrunner/executive producer Prentice Penny always knew the show would last five seasons, bringing its storylines to a satisfying conclusion proved challenging.

The first version of the finale was set five years in the future with Rae’s Issa Dee character and Molly traveling in Morocco. But, just two weeks before filming began, Rae decided to change things up.

“It just wasn’t right,” Rae says of retooling the story. “It was fun, but it just wasn’t the proper send-off to L.A. and it just wasn’t the story that we wanted to tell, the story that we’ve been telling this season and with the series.”

Rae re-wrote the script, changing pretty much everything except for the final montage. Issa’s driving tour around South L.A. — driving past The Dunes, her old apartment complex, then by a Lawrence look-alike outside Rite Aid, and spotting Frieda (Lisa Joyce) and Sara (Sujata Day) outside of We Got Y’all — represented the character’s growth over time.

“It was so important for Prentice and I to look at places that were important to shaping Issa, and sending off the locations that were so central to her own journey,” Rae shares.

The half-hour comedy’s slightly extended running time was a gift to the fans who have been petitioning for hourlong episodes since the series debut in October 2016.

“We really tried to give a full hour and then when you give these cuts to the HBO team, they’re like “OK, let’s trim this, maybe don’t need this …” and so that’s how we ended up with 41 minutes,” Rae explains. “It’s out of our hands. But yes, wanted to pass the [usual] time a little bit.”

Here Rae dives deep with Reporter Door into the finale’s biggest moments, from the conclusion of the Issa/Lawrence/Nathan love triangle to Issa and Molly’s tearful talk after the show’s big wedding. Plus, she dishes on the fate of Issa’s “Mirror Bitch” and that “Bossy” needle drop.

Tell me how you came up with the birthday plot device, where we check in with everybody on each main character’s birthday. Where did that idea come from?

It was twofold. One — this season has been the story of growth for these characters. And, for me, it was really exciting to tell a story through time, with birthdays as the literal device of getting older and growing. Birthdays are how we started the show, so to be able to culminate that way was really like poetic justice for me.

And then thinking about my own life, and wanting to tell the story of Issa and Molly trying to maintain the friendship that they have dutifully kept over time with the circumstances of life, just modeled it after my own life and friendships. I have friends that I’ve had since high school, and we’ve gone from kicking it every Friday guaranteed, to growing up and dealing with families, life, loss and all of those things. Sometimes the only guarantee that we’ll actually be able to hang out is birthdays and I think there’s a sadness to that, but also just the reality of getting older and into your 30s. And I think there is a naivete of thinking, “We’re always gonna be friends and we’re always gong to kick it” but that doesn’t always happen and telling Issa and Molly’s last moments before we see that — and the four girls — just really spoke to that.

Going back to the pilot, Issa was so worried about spending her entire 20s with the guy she wasn’t going to end up with, and then look where we are!

Look who she chose! And, you know, who knows? I think that they stay together, but one of the things that excited us about these endings for is that they’re not really endings, they’re kind of beginnings. If we were to continue to Season 6, there are stories to tell with all of these characters still. There’s so many new things that they’re exploring — Molly and Kelli (Natasha Rothwell) start a firm together; Kelli’s own personal developments in life and probably new marriage; Issa’s decision to stay with Lawrence (Jay Ellis), and does that mean that there’s a relationship there with Elijah; and, of course, Tiffany (Amanda Seales) being in Denver and having a second child. There’s just so many different factors and that was really important to us to feel like these characters’ lives would still continue.

On that note, let’s start with Issa’s love life. That Issa/Lawrence/Nathan love triangle was a major focus of this season, but at what point did y’all decide Lawrence was going to be the one?

Um…at the end. From jump, I was pretty insistent that I didn’t think that Issa should be with Lawrence. And, as a writer and coming into that writers room, I personally felt like I didn’t want that for Issa Dee. Then as I started to play Issa Dee [this season] and we started to shoot, I just found myself like legitimately missing Lawrence and feeling like, “Did I give up too soon?”

I stand by the fact that Issa should have broken up with Lawrence during that time [at the end of Season 4]. I think that was the best decision she could have made for herself and for them, because he was going to be in a toxic relationship and needed that time to adjust to being a father. And she needed to go on the journey that she went on, and focus on rebuilding her friendship with Molly. I maintain that that was the best decision for her at that time, and with time things change. That’s something special about just being a human and living is that over time, you have the right to change your mind. You have your right to reflect and decide what’s best for you in the moment. And that’s the journey that we both went on.

To clarify, you decided Issa should pick Lawrence while filming Season 5?

Even after determining to rewrite the existing finale, it was just like, “Ehhh.” I was still teetering. And then it was just like, this is what I want, and I’ve kind of been denying myself and I’ve been making Issa deny what ultimately is her happiness and her choosing to be happy, like she discussed with Lawrence. One of the other things that one of our writers [co-executive producer] Laura Kittrell, brought up is just the idea that, in Season 4, we essentially set up the idea that Issa and Lawrence were soulmates. And by denying the chance for them to get together, we’re basically saying that Issa doesn’t deserve her soulmate, which is so antithetical to her victory and her going after what she wants. So that was also went into the final decision to make them end up together.

Issa and Nathan also have a conversation about why he walked away, and telling her that this relationship is toxic and this isn’t working for him. What did you want to explore when closing their chapter?

Following Nathan this season, we watched him grow and be a better communicator. In many ways, he’s choosing himself. He has chosen himself in a selfish way before, but I think this time, for the progress that he’s made, I think he sees that this relationship with Issa, that she’s not ready for him. So we wanted to give him a just ending as well.

Was there ever a version where Issa wound up totally single at the end?

We talked about it in the room, does Issa end up by herself? In some ways, I felt like Issa chose herself at the end of Season 3, in what I thought was like a really beautiful season finale. It’s just like, “I’m going to focus on myself and build myself and not worry about this man — Nathan at the time —  coming back.” Maybe that happens again? We also discussed [a version where] we see Issa come home and somebody’s there, but we don’t know who it is. But for me, I just wanted some closure in that department. I, as a viewer, wanna know.

Yes, you could not pull a “Sopranos” on that; people would not be pleased.

Yeah, no thank you. I wasn’t trying to deal with that. [laughs] But, yes, just as a viewer of the show myself, I just approached it like, “I want answers.” And if we were to continue to show into Season 6, what am I looking forward to?

Now on to Issa’s career. As Lawrence says in this episode – “You’ve gone from We Got Y’all to I’ve Got Mine.” The Blocc is hot now! What did you want to show with its evolution in this final episode?

We wanted to show Issa being successful in her community, in her own way. In Episode 8, we painted a picture of her imagining that things have to happen one way or the other. That’s not always how life works. I think the finale really merged Issa Dee and me in a way, in terms of, aspiring and just keeping your head down and hoping for the best. As you can see in her office, things worked out, things are okay. I’m so happy with where I am at this point, and that was just important for me to showcase [Issa Dee] as aspirational.

We also see Molly and Taurean (Leonard Robinson), who have become one of the internet’s favorite couples very quickly. What do you make of that early fan reaction — especially after their edible adventure in Episode 9 — people are like, “Oh, they’re cute”?

A pleasant surprise. I hope you rub it in Yvonne’s face — apropos of nothing, I’m just saying that. But I love that people’s reaction to Taurean has been super-strong and that people really want Molly to be happy, because that’s something she really wanted for herself — to be able to find someone who would get her, who has seen her arguably at her worst and still loves her and wants to be with her. That is what Molly deserves. I’m so happy for her ending.

Was Molly’s wedding a bit of a nod to your photo shoot? [In July, Rae married Louis Diame in a private ceremony, referring to the event as a “photo shoot.”]

You know what… [cracks up laughing]. Yeah, no, no, it was not at all, but there are a lot of similarities there. Yvonne was present [at the wedding], and she came up to me and said, “Like really? So two finales?” And we started dying laughing. Yes, it was very eerily close, but not at all.

There’s so many moments between Issa and Molly. What will you remember about being in those scenes with Yvonne?

We’ve said this before, but this show is about the true love of the two of them, and there’s a little heartbreak, just feeling that loss. And they’ve already dealt with the loss of life circumstances drawing them apart. That moment of appreciation from Molly was also important to showcase, because, this season, we’ve also watched Issa be a better friend to Molly. We started off the show with Issa being selfish, kind of a user and aloof to how her actions affect Molly, and then we watched her continually be there for her and support her in a way, and to have Molly acknowledge that meant a lot to Issa.

I mean, they literally start the show with the “Broken Pussy” rap…

Yes they did — that’s our introduction to the shakiness of those two.

You have a beautiful callback to that in the final needle drop of the series. The first few notes hint at a replay of “Broken Pussy” but instead “Bossy” by Kelis plays. When did you decide to do that? 

In the final edit, I knew that I wanted a callback song, so our editor tried a different song there and I thought, “It’s nice,” but it just didn’t feel … I don’t know, it just didn’t feel appropriate for that moment. For me, when I think about one of the most memorable songs that really shaped how the audience was introduced to Issa, and also shows the trajectory of her journey — like she’s a boss now — the “Broken Pussy”/”Bossy” hybrid felt like the best option.

That song follows a scene with Issa looking in the mirror, putting on lipstick — in another callback to the first episode — and then getting a final phone call from Molly. Issa goes with a nude lip — is that signifying that she’s OK with who she is without trying on these other characters?

Yes, I mean that final mirror shot is something that we also came up with in Season 3. We were actually going to end, instead of Issa sitting on the couch looking at her new apartment, we were going to have this moment where she walks away from her mirror. And I was like “Hmm… that sounds more like a finale moment and I really wanted preserve that for the finale.”

Issa walking away from her mirror just signifies so much, because, from jump in the show, Issa’s mirror has always been a safe space for her to just be who she really is in her bathroom, before she goes in the outside world and kind of lies to herself and others. Then, as the series progressed, it’s become sort of her crutch in terms of making decisions. So, her being okay with seeing her reflection in the mirror and walking away is our way of signifying the fact that she’s okay with who she is and she’s the same in her bathroom, as she is in the outside world. That felt like a full circle moment to have.

So, Issa’s “Mirror Bitch” is totally gone at this point?

She doesn’t really need “Mirror Bitch” in the same way. I think Mirror Issa and Issa are together — they’re married at this point.

This is the final bow, the final goodbye. What are your last words on “Insecure”? What has this meant for you?

I would say, from jump, this show has been a very specific story about Black people, Black women, and I’ve stated that. And I’ve seen people want to make this show their version of what it should be, and I really, really appreciate the people who have stuck with the story that we’ve wanted to tell, which is a journey about a girl who is trying to figure out who she is, where she’s going, and this love story between two women, two friends.

I have just cherished every part of this experience. Thank you for watching these characters grow and thank you for loving these characters. Thank you for watching their mess and thank you for watching them learn from their messes and mistakes. I really hope people cherish this show as they cherish their friendships, and that it lives on with them for years to come as my favorite shows did for me.

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