There Is Only One Insecure Love Affair That Truly Obsesses Issa Rae

.@IssaRae discusses how she knew it was time for the final season of #Insecurehbo and who—if anyone—Issa Dee will end up with.

Insecurehbo

10/23/2021 5:16:00 PM

.IssaRae discusses how she knew it was time for the final season of Insecurehbo and who—if anyone—Issa Dee will end up with.

Just before the premiere of the final season of “Insecure,” Rae discusses how she knew it was time to say goodbye, persistent comparisons to “Girls,” and who—if anyone—Issa will end up with.

I think it’s fair for the most part. Season one, I was more frustrated with theAwkward Black Girlin season one, and I was like, “No. It’s unfair. We will never stand on our own and we will be pitted against each other.” That, to me, was a no-no. Now? Make all the comparisons you want. We are our own show.

Insecure”Storylines about work don’t always work on TV, but they do on.”In a lot of ways, Issa has “made it,” but that comes with new problems. We see that in the new episode, where she’s planning a fashion show for a local artist, Crenshawn, and getting notes from a corporate boss about toning it down. Have you had that experience where you’re having to reconcile pleasing powerful people and doing what you think is right and true?

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Issa Rae on How ‘Insecure’ Will Be Remembered After Its Final Season: “It Was for Us, by Us”Rae, Yvonne Orji, Jay Ellis and showrunner Prentice Penny celebrated the fifth and final season of the HBO show at Thursday night's premiere.

“ Sex and the City” —I think because of the HBO connection, the female friendship, the love and the sex. How did those comparisons strike you? I think it’s fair for the most part. Season one, I was more frustrated with the Girls comparisons. I wanted to stand on my own two feet because I had been continuously compared to Lena Dunham since my Awkward Black Girl days and, love her, respect her, but as a creative, when you’re coming out, you want to do your own thing. HBO wanted to pair us with Girls in season one, and I was like, “No. It’s unfair. We will never stand on our own and we will be pitted against each other.” That, to me, was a no-no. Now? Make all the comparisons you want. We are our own show. I have felt—and maybe it’s changing now in terms of traditional markers like Emmy nominations—that “ Insecure” did not always get the level of love and buzz it deserved. Did you ever feel that? I didn’t feel that way, but I know that some of my colleagues—some of the other EPs (executive producers)—felt that way. I cared more about: Does the audience connect with the show? Is it still good? Are we happy with it? Yes, acknowledgment excited me, because more people find out about the show. If you’re Emmy nominated or Golden Globe nominated, it piques their curiosity, so that mattered to me. But I tried not to focus on it. Storylines about work don’t always work on TV, but they do on “ Insecure .” I’ve never felt so invested in characters’ careers and professional growth. Why has that been an important part of the show for you? It’s an important part of my own identity. A lot of people have asked me over the years how much I identify with the character, and in those first couple of seasons, I felt like Issa was the younger version of me. By the time I had done the show, I knew who I was, and I was confident in the path that I was on, and we were creating this character who’s not yet. So much of your 30s is about establishing yourself and understanding what your purpose is and finding your passion. The short answer is: It just mirrors my own journey. In a lot of ways, Issa has “made it,” but that comes with new problems. We see that in the new episode, where she’s planning a fashion show for a local artist, Crenshawn, and getting notes from a corporate boss about toning it down. Have you had that experience where you’re having to reconcile pleasing powerful people and doing what you think is right and true? One thousand percent. That comes with holding the door open for other creatives in the industry. I’ve had plenty of times when I believed in someone and then had to navigate, or help them navigate, the corporate executive notes. I’m dealing with that actively, and it sucks because you almost become part of the system. You become the bad guy, when all you wanted to do was just uplift this person. You’re wrangled in that red-tape culture. It’s a balance, and it sucks that it has to be that way. But that Crenshawn situation is one that we wanted to live in a gray area. Issa believes in Crenshawn. She was just trying to get his show made. photo: Merie Weismiller Wallace / courtesy HBO I read that “ Insecure” is only the second comedy created by and starring a Black woman. That seemed really wild although believable at the same time. Was knowing that a motivator? A burden? I didn’t know that making the show at all. It was in a magazine or on one of those lists, and I was like, “Oh, that’s fucking crazy.” I guess I didn’t think about the creation part of it. Part of that was my problem to begin with: We don’t have shows that are solely centered around our experiences or haven’t had those shows since the ’90s. That was very much in my mind: I want to represent the shows that I grew up watching for this age. But I also don’t want to represent all Black women. Don’t put that on us, because it’s impossible. It used to be that whenever a show ended, people assumed that the star of it wanted to go make movies. Is that part of your plan? I’m definitely being guided in that way. I feel like that is “the path,” and I’ve fallen into that, like, Oh, is this what I’m supposed to be doing? But I love TV so much. Yeah, movies are cool, but television, you get to live in a world, and I love creating worlds. There’s just something more interesting and compelling about television to me. I want to ask you about the men in Issa Dee’s life. Some people are Team Daniel; others are Team Nathan (Kendrick Sampson). I am a basic Team Lawrence lady. Can you reveal any allegiances you have? I have shifted several times. I have been Team Daniel. As an artist, I identify with his insecurities, his pride. I do think that he tried to be there for her and it mirrors a relationship I’ve had in the past. There’s just a soft spot in my heart for Daniel, but I don’t think, at that time, he was right for her, and I think that she was right to move on from him to stand on her own two feet. I’ve been Team Lawrence; I’ve been Team Nathan; I’ve been all over the map. I know you can’t tell me who Issa ends up with, if anyone, but can you talk about the decision-making process or any conversations you had behind the scenes about her love life and how to end it? We had a lot of conversations. We did a lot of voting. The room had very strong opinions. There was a lot of butting heads, so I don’t know who is going to be satisfied by this ending. I don’t think we’re going to satisfy anyone. You can’t. You can’t satisfy everyone, but there was a lot of discussion and a lot of personal change that happened throughout the season. I, as a writer, changed my mind a lot, and that will be reflected. The guys aren’t just afterthoughts on “ Insecure.” They’re real parts of the show. I am rooting for Lawrence so much, not just as a boyfriend for Issa but because we saw him sitting on the couch for a whole season and now he’s thriving! Was that always a conscious decision? That was not the plan, but after we cast Jay, he was just so good in the role, you wanted to see more of him. That was something I saw at the watch parties. Jay brought it from day one, and you do become invested in him and identify with his struggle. I understand what the Lawrence hive sees in this man. They see themselves in him. But the love story we’ve always been the most obsessed with is Issa and Molly. The