In the run-up to the premiere of the fifth and final season of Insecure on Sunday, Issa Rae is feeling nostalgic. Last weekend, Rae—the show’s creator, star, and muse—hosted a series of watch parties with fans in Los Angeles. While screening seasons one through four of the Emmy-nominated HBO comedy, Rae cringed at points (technical stuff she’d rather not highlight) but, mostly, “I was just really proud of the growth,” she told me this week, fresh off a red-eye to New York in truly fabulous glittery eye shadow.
When Insecure premiered in October 2016, 28-year-old Issa Dee—the fictional, younger version of Rae—was in the throes of a quarter-life crisis: living with her lost, longtime boyfriend, Lawrence (Jay Ellis), but eyeing a sexy ex, Daniel (Y’lan Noel); toiling at a nonprofit, We Got Y’All, which was rife with white savior vibes; and bonding over it all with her best friend, Molly (Yvonne Orji). Insecure nailed that elusive blend of funny, sharp, sexy, and emotionally impactful. Issa was searching for herself—in love, career, and friendships—and when she rapped at her reflection in the mirror, she was as awkward as any of us. The characters fell in and out of love with each other and, during priority Sunday night viewings—with a second screen for Twitter commentary—I fell in love with Insecure.
Five years later, the growth is apparent on- and offscreen. Both Issa Dee and Rae, who got her start with her YouTube series, The Misadventures of Awkward Black Girl, own their own companies (Rae’s production company, Hoorae, has an overall deal with HBO to continue making shows for the network/streamer); Lawrence has detached from the couch; and the sisterhood between Issa and Molly is ever evolving. But the beauty of Insecure is that even with seasons of personal and professional progress, and a sprinkling of weddings and babies, there is still awkwardness (“Art imitating life,” Rae jokes) and plenty of mess. Season four ended with Issa and Lawrence, all grown up and self-assured, on the cusp of a reunion—until his ex, Condola (Christina Elmore), resurfaced and announced a pregnancy.
I spoke with Rae about how she knew it was time to say goodbye, persistent comparisons to Girls, and who—if anyone—Issa will end up with.
Vogue: Issa is sitting on a panel at Stanford in the season premiere, and she gets a question that shakes her: “How did you know when you were on the right path?” It made me wonder: How did you know that ending Insecure was the right choice for you?
Issa Rae: I just felt it from season one. I wanted a five-season show for this particular story. I’m a restless person. We’re going to be asking people to commit five years of their life to something. You kind of get restless after that fourth year, and I want to love these people. I want these people to still want to be on the show, from the writers to the actors to the crew.
Insecure has been compared to Girls and 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.
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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 Insecure fandom was upset in season four when Issa and Molly were not friends.
Oh, boy. Yes.
Were you just thinking, even though they’re best friends, they might not be on the same page every single season of their lives?
We were naturally telling a story where they would bump heads. It really interested us to discuss these friendship breakups that happen, because I’ve had several, and they don’t really get the same attention as romantic breakups. Issa and Molly has always been endgame, but we just wanted to portray what that looked like.
Speaking of the fan reaction: I have to ask you about the Condola hate. It’s really funny, but also sometimes really virulent?
It’s hella funny. Shout-out to Christina Elmore, because she is the best sport about it, but people are crazy. She was actually pregnant and people were wishing things on her. I was like, “Fall back. She’s playing a character and she’s playing it beautifully.” I think, to your earlier point, people are rooting for Lawrence, so people view her as the evil person who is taking his dreams away, you know, blowing his life up, as he puts it. Condola is an equal partner in this. Lawrence is just as culpable, so it’s so funny that he’s not getting as much of the backlash.
People have nicknamed her Coronavirus.
People called her Catapult the other day, and I died. I was like, “Y’all are doing the most.”
The interview has been edited and condensed.