After more than a spell of discord and distance between the treasured friends last year and throughout this fifth and final season, the four words from a now married Molly encapsulate and navigate the Prentice Penny directed and Rae penned “Everything Gonna Be, Okay?” deftly. Aware of the debate, definitions and competing perspectives that the end of Insecure will incite, Rae, Penny, the writers and team took a long tail approach with years playing out over the tenth episode of Season 5 through birthday celebrations.
Put it this way, and remember this last season of Insecure was one of my Top 10 TV series of 2021, if you thought the “messy shit,” to quote Kendrick Sampson’s Nathan, that went down between Nathan and Lawrence (Jay Ellis) after the latter professed his love for Issa at the moving to Colorado party of Tiffany (Amanda Seales) and Derek (Wade Allain-Marcus) in the penultimate “Out, Okay” episode was bracing, the finale was prophecy fulfillment in action.
— Yvonne Orji (@YvonneOrji) December 27, 2021
Of course, this being the show that was spawned in 2016 in part out of creator Rae’s The Mis-Adventures of Awkward Black Girl web show, it was far from all cakes and candles, exploding or not. Amidst the passage of time and the emergence of loss literally and figuratively, Orji’s Molly put a ring on her finger and was good with it, and was very good with her friend Issa Dee and the journey their relationship had been on. Correspondingly, as there were pregnancies and regretful moves among other primary characters and big moves for Dee’s the Blocc company, Issa tells a still courting Lawrence that she’s alright with taking another chance on things working out for them.
And if that domestic bliss birthday scene at the end of the episode is any indication,
With all that, the very busy Rae, who inked a lucrative five-year pact with WarnerMedia earlier this year, spoke with me about how Insecure got to that end, what she thinks about the reactions to the finale and what the Emmy-winning show’s legacy is for her.
DEADLINE: So, you finished filming a while ago, but now the finale is out in the world, how does that feel?
RAE: I’m really just relieved that it’s out there, that we were able to end the show on our terms and tell the story that we wanted to tell, and I hope people appreciate where these characters ended up and know that this is more reflecting of a new beginning for them, which is the approach we took to this finale. It’s just like what stories do we want to play out if this did get a Season 6 as our lives in the Insecure world continue. I know people are going to have a lot to say as they always do but I’m really proud of our finale.
— Issa Rae (@IssaRae) December 27, 2021
DEADLINE: Was this the ending you always had in mind, or, if you don’t mind me asking with all the threads that entwined here, was the finale a work in progress over this season? – and I’m not just talking about Issa and Lawrence ..
RAE: (LAUGHS) It was a work in progress for sure. I mean, that bathroom moment with Issa and Molly was something that Prentice and I talked about from the jump.
That was just something that I visualized, and he executed it so perfectly and beautifully, but the elements of the finale definitely changed. At one point, we wanted to jump five years into the future and show Issa and Molly in Morocco and tell that story. While sudden, it did not feel like the right ending, especially spending so much of our finale away from L.A., which has been a character in the show.
DEADLINE: And birthdays became one in the finale, which really hung it together as a backdrop …
RAE: I thought about my own life and my own friendships and how hard it is as you get older to get together. So, birthdays being a staple and almost a guarantee for us despite life’s circumstances, to stay in touch and getting together gave me the path to tell the story of Molly and Issa, not necessarily growing apart but like physically being unable to gather because of life’s circumstances and only get together through birthdays. It was a way to o show that they were just always going to be there for each other in some capacity.
DEADLINE: Series finales are so hard, and I would guess even more so for a show like Insecure, with its finely tuned balance developed over the years. I mention that because you mentioned that you think people are going to have a lot to say about the end, as they have week after week, and this is where I’m asking about Issa and Lawrence getting back together and in apparent domestic blended family bliss – you know the reaction is going to be strong to that with a lot of fans pounding their digital chests in social media rage. What’s your take on that reaction?
RAE: I don’t give a fuck how people react to it, because to answer your question, it was a journey for both of our characters, to be honest.
DEADLINE: How so?
RAE: In the beginning of the season, as soon as we got in the writer’s room, that was a burning question and I was just like no, they’re not ending up together. There was just no way and that was an argument. Like we had the argument that the girls have in episode seven about why Issa should have moved past Lawrence and move off Lawrence. Like Kelli and Molly used to say “I don’t want her to be a stepmom. I don’t want this for her.”
He’s clearly grappling with a lot of these issues. There’s going to be drama and I want better for my girl, and so, we had different endings in mind and different journeys for her. Then, when I became Issa Dee and we started shooting the show, there was just a part of me that really missed him and that wanted him. I realized that there was a happiness that she/I had with him, and I stand by the fact that they should have broken up in that first episode because Lawrence was going to be in a toxic, messy relationship and she was going to be wrapped up into all this.
But I am a firm believer that sometimes you need time, and if it’s right for you and you want it, then it can be yours.
Happiness being a choice has been a theme for these two characters for the last couple of seasons. I can choose to be happy with you and I want to choose to be happy with you and if it doesn’t work out, then fuck you. I think that that’s what our character wants at the end of the day, and I know audiences will have opinions. A lot of people hate Lawrence, but luckily, it’s not their relationship.
Uh oh, Issa been thinking about Lawrence…… #insecurehbo
— Jay Ellis (@JayREllis) December 27, 2021
— Yvonne Orji (@YvonneOrji) December 27, 2021
DEADLINE: The definitive. However, another relationship a lot of viewers had with the show and through Issa Dee via Issa Rae and team was with Los Angeles. Over the years, it’s become canon that Insecure is partially a love letter to friendship, true and deep, but the series was also a love letter to the City of Angels. As you said today, L.A. has been a character in the show and that character got a big send off as much as Molly and Issa in some ways, why was that last poignant drive around so important to include?
RAE: I remember being in Arizona last year trying to like think about what this finale was going to be and I was just driving and one of my favorite songs came on the radio, which is ‘Rose in the Dark’ by Cleo Sol. That was what we ended up using for a song, and I just got emotional thinking about how I wanted that final scene to be, of her just revisiting her past and like literally driving on the journey to the landmarks that made her who she is and figure out where she is today.
You know, L.A. has been such a character and these locations that she visited, Prentice and I made up a list of the spots that we just knew meant so much to Issa and the show in general. It just felt right to also give that city a sendoff in the same way we were giving these characters the sendoff, and thanks for noticing that.
DEADLINE: Thank you for that.
Issa, as we come to the end of this year, everyone’s looking back and years always feel like they encapsulate something, but I was particularly struck by that final scene with the mirror because mirror Issa and real Issa have been, obviously, not the closest of sisters over the years to put it mildly …
RAE: (LAUGHS) No!
DEADLINE: Just sayin’, but looking at that final scene in the bathroom of Issa and Lawrence’s house and dinner with Lawrence’s daughter (name) is about to be served, it’s all good — mirror Issa Dee is gone. There is such a precision to this finale, yet of everything you guys got in there, it felt like that scene could have dangled, yet you cut it short. So, long question short, why?
RAE: Across the show, the bathroom, mirror Issa in particular, that’s always been a place where real Issa could be her real self, where she wasn’t in the outside world. So, there was always a separation of who she was in that mirror versus who she was outside. As the series progressed, of course, she started to lean on that mirror a bit more and it became a source of a lot of her insecurities. This show in its entirety has been the journey of her growing into this secure person. Secure in who’s she’s not, who cures her insecurities, and I think not having her rely on that mirror in the end was just a symbolic way to show that she was kind of good on her own. She’s now the same in the bathroom as she is in the outside world and she’s good with that.
— insecurehbo (@insecurehbo) December 27, 2021
DEADLINE: Which is so much of how this finale functions so well, in my opinion – you get us to the place where the show circles itself. Now it is all done and a bit of time has passed on the finale for you, and you have a full dance card of projects, companies and initiatives, what are you most proud of about Insecure?
RAE: Showcasing regular black people. Making regular black people compelling without some of the tropes and stereotypes that sometimes the industry deems compelling about our lives and our history. Also, being able to also be a pipeline for other black creators and creatives and to inspire the industry to take a chance on other stories like this. I’m really, really proud of that. The pipeline in particular is something we set out to do but to have such an influence in this way is not something that we pictured us being able to have.
DEADLINE: What other shows did you draw on for inspiration in getting Insecure to the finale you wanted it to have?
RAE: I mean, I thought about a lot of my favorite finales that stuck with me. You know, Fresh Prince is one. Six Feet Under is one, Breaking Bad is one, but also a lot of my favorite shows, to me, haven’t gotten proper ending. I just thought a lot about that a satisfying ending and there is a satisfying sense of closure, but also, I could see where this story could continue if I wanted to. I could still imagine what these characters, with the exception of like Breaking Bad, but Six Feet Under, to me, is like a representation of an ultra-satisfying finale in addition to like Fresh Prince.
DEADLINE: So, is there any sense that we might see a return of Insecure in some form or another, or some of these characters?
RAE: Not on my watch.