‘Insecure’ Broke Ground by Embracing Imperfection

“Insecure” begins its final season by looking backward.

In the season premiere, which debuts Oct. 24 on HBO, the best friends Issa Dee (Issa Rae) and Molly Carter (Yvonne Orji) meet up at Stanford University for their 10-year college reunion, having spent most of last season fighting and apart. Over an eventful weekend, they reminisce about the origins of their relationship and pledge to move forward together, once again firmly in each other’s corners.

It suggests that for the final stretch, “Insecure” is returning to the thing that made it so appealing for Black viewers especially, and so subtly groundbreaking for premium cable: consistent focus on the ups and downs of Black women’s friendships. Created by Rae (then known for her web series “The Misadventures of Awkward Black Girl”) and the veteran comic and showrunner Larry Wilmore, “Insecure” was only the second comedy created by and starring a Black woman when it debuted in 2016. (The first was Wanda Sykes’s “Wanda at Large,” which premiered in 2003 on Fox.) “Insecure” briefly overlapped on HBO with “Girls,” which ended in 2017 — both descendants of the network’s “Sex and the City,” but which swapped the Blahniks and Birkins for millennial angst and awkwardness.

“Insecure” countered the racial homogeneity of those New York predecessors, but it also stood in contrast to other shows and films set in Los Angeles. Neighborhoods like Baldwin Hills, Windsor Hills and View Park (where Rae grew up) had rarely been seen onscreen; if South Los Angeles was portrayed at all, it tended to happen in movies like “Boyz ’N the Hood” and “Menace II Society” that depicted predominantly Black communities like Watts and Inglewood (where Rae’s father had his dental practice) as plagued by gangs and gun violence. Rae has said her goal was to make those neighborhoods feel as sexy as any other place in the city.

Part of that sexiness came from the look and sound of the show’s world. Melina Matsoukas, best known when the show debuted for having just directed Beyoncé’s “Formation” video, set a visual tone as a director and executive producer. The experimental R&B singer Solange Knowles served as a music consultant. (The neo-soul legend Raphael Saadiq also composed music for the score.)

It also came from the fashion — Molly’s couture work wardrobe, Issa’s chic political T-shirts — and from the dazzling array of natural hairstyles. The aesthetics made for a sleek, inviting backdrop to the show’s trailblazing casting, which centered two dark-skinned Black women as stars and romantic leads.

But the most revolutionary aspect of “Insecure” was the abundance of decidedly unsexy moments — when Issa and friends messed up, hurt themselves and others, indulged in the kinds of mistakes and bad decisions most of us make as young adults.

“True representation is the ability to show your vulnerability and be able to say, ‘I don’t have it all together, just like the next white person doesn’t have it all together,’” Rae said recently. “I think the show gave Black people permission to also be like, ‘You’re right: We are insecure.’”

Like Rae and Matsoukas, most of the show’s creative team had new jobs or new levels of responsibility when “Insecure” began. The showrunner Prentice Penny and the executive producer Amy Aniobi had never before filled those positions. Playing Molly was the first major acting role for Orji, a stand-up comedian. Five years later, they are a tight-knit group of veterans, proud of what they created together.

For a recent video interview about the end of “Insecure,” Rae and Orji were together in Miami; their co-star Jay Ellis, who plays Issa’s intermittent love interest Lawrence, dialed in from that city’s airport; Aniobi was in New York City; and Matsoukas and Penny were in Los Angeles. Despite being all over the country, their intimacy was genuine and inviting. There was plenty of ribbing — Penny’s oversized Green Bay Packers cap and Ellis’s bad phone reception were popular targets — but after nearly every joke came sincere reflection about a colleague’s talent or insights. These are edited excerpts from the conversation.

Issa, when “Insecure” debuted, you described it as a show that wasn’t exclusively about the struggle of being Black but rather “just regular Black people living life.” Looking back, did it live up to that vision?

ISSA RAE: I think we nailed it. The goal was to elevate regular Black people and make us look as beautiful in our regularness as humanly possible. I think we achieved that.

PRENTICE PENNY: One of the problems we show is that Black people face racial microaggressions at random. Like, in Episode 3 of the first season, when Issa Dee realized that her white co-workers were leaving her out of their emails. Not everybody’s shot by the police, but everybody knows what it feels like when white people are talking about you behind your back. Those are the things that felt regular, right? Or what is life like for a Black person on any given Tuesday? A day that’s not special, but super regular. That was our North Star.

RAE: And when we did include Lawrence getting pulled over by the police, a high tension moment that we know ends up so fatally for so many men and women in our community, we asked ourselves, “How does that encounter affect the next events of your day?” We deal with these things all the time and do not get an opportunity to pause and reflect. Instead, Black people experience microaggression or racism and keep pushing. You may come home mad and yell at your partner, or you might journal. “Insecure” is more interested in those moments and how they affect your day-to-day life.

PENNY: Issa said in the writers’ room at one point: “When you’re white, racism is a period. Like, ‘This is wrong, this needs to stop, period.’ But when you’re Black, it’s a comma.” It’s like, this racist thing happened to me, but I still have to go pay bills, still have to drive and go home and see my kids. Yes, this thing happened, but how are you going to deal with it?

In 2016, “Insecure” and “Atlanta” broke new ground as comedies about Black millennials. Did any of you ever feel pressure to speak for your generation?

MELINA MATSOUKAS: I never felt the burden of having to speak for an entire generation of people. The task we felt was to show these characters and this environment authentically. That meant actually shooting in the neighborhoods these characters are from, speaking to and incorporating those people into our storytelling, using strong female relationships and all the things that are authentic to a real, vibrant community and the world where Issa Dee comes from.

Was representing Black people of varying class statuses part of that honesty? The characters Issa and Lawrence, for example, live in the Dunes, an apartment complex with predominantly working-class Black residents, even though they graduated from Stanford and Georgetown.

RAE: To Melina’s point, it was authenticity. I graduated from Stanford and didn’t have a job, so I moved back to L.A. into my parents house, and the first place I moved to after that was a Dunes-like apartment complex where you have people of different classes.

PENNY: There’s this expectation that we have to be perfect and excellent all the time. I remember we when we were pitching it with the title “Insecure,” there was push back about that because insecurity is not usually associated with Black people. That was such a moment for Issa, Melina and me, and it made me realize, “No, that’s even more reason we want the show to be that.”

YVONNE ORJI: They were like, “You guys are flawless, you’re fierce, you’re ——”

PENNY: “So dope, you’re so dope.”

MATSOUKAS: I’m literally feeling uncomfortable and insecure right now.

ORJI: This conversation is making me insecure.

JAY ELLIS: That is part of the reason this show never felt like a burden. Because the burden is being excellent all the time. The burden is the expectation that we have for what a Black man or a Black woman who went to Princeton or Stanford is supposed to be like, or what Molly had to go through being in that white law firm, right? But when we got to do the show the way Issa, Prentice, Melina and Amy wanted to do it, we didn’t have to wear a mask for anybody or live up to anybody else’s expectation. This is actual freedom.

For most of you, this was your first time leading a project of this caliber. How do you look back on that risk now?

AMY ANIOBI: I think back to our first production meeting when someone asked a really good question. And then I realized, “Oh, I’m supposed to answer that?” It was a bit like working at a teaching hospital; we were all learning for the first time together. That contributed to why we had each other’s backs so hard.

PENNY: We were trying to create a safe space for failure. We’re going to open the door as fast as possible to get many people in and make a safe space for Black creative people.

ORJI: What Issa has started for me is a chain reaction. With my specials or next projects, I’m pulling in people that I’ve seen doing amazing things but haven’t had that big break yet. I’m giving them a chance. White people are allowed to do that for their friends.

ANIOBI: If you want to get enraged, read the Wikipedia for “Seinfeld.” I’m like, what? It had so many tries.

PENNY: And I’ve worked with writers from “Seinfeld” and “Friends” after those shows ended, and they still get overall deals all the time. Those shows are 20 years old now. They still believe, “I think those white people still got something in them.”

Even though your show was on HBO, it often felt as if it was written for a Black audience. Characters like Issa and Molly started off code-switching and working in predominantly white offices, and they quit. Their worlds and the show itself started getting more and more ——

ANIOBI: Blacker.

RAE: With “We Got Y’all,” we just felt tired of telling those stories. There is this pressure for Black writers to talk about the Black experience within a white context. In Season 1, we were briefly encouraged to tell the point of view of the Frieda character [Issa’s white colleague at the nonprofit, played by Lisa Joyce]. Why would we do that?

ORJI: By Season 4, Issa was out of that environment, and Molly went to a Black firm. And when you put the characters in a Black space, you also told a realistic story of what that looks like, too. When Molly goes from the white firm to the Black firm, it’s not like, “Ah! My people!” It’s like, “Hi, this other place did it differently …” and they were like, “You can go back there.” But at the same time, she’s like, “Whatever I lost coming here, I gained this other thing that you can’t put a price tag on.”

MATSOUKAS: Those story lines really paralleled what was happening to us within the industry. We all came together and we were all coming from a place where we were othered, where we were the only Black person working in white spaces. Then naturally gravitating toward one another and really enjoying the freedom that comes with working with each other, speaking the same language and not having to code switch. Now we just have one code.

RAE: Now we are the code.

Making a complex friendship between two dark-brown complexioned Black women, Molly and Issa, the heart of the show still seems rare, even today.

ORJI: That was very refreshing to see that casting breakdown and realize, “Hold up, she’s talking about me.”

RAE: This is based off my real friendship. So I wasn’t interested in the trope of one light-skinned and one dark-skinned friend. I was very interested in staying true to that authentic friendship, and we often don’t get two dark-skinned Black woman leads. So that was a mandate for us, to make sure that was showcased.

MATSOUKAS: We really wanted to be a part of redefining what beauty looked like. I remember going to film school and them being like, “If you cast a Black woman as your lead, it won’t be a marketable film.” That’s literally what I was taught in school. So to show that beauty exists in all different shades and colors, and that these women and can just be as sexy as anyone else, was really important for all of us.

ANIOBI: Some of the storytelling felt almost like wish fulfillment for us as dark-skinned Black women. It was exciting to be like: “If we were the center of the story, what would happen? How would it happen?” There was so much of it, especially in the early seasons, where we were like, “Well, what would you expect if it were your story?”

RAE: Portraying a desirable dark-skinned lead over the years — this is something I’m only recognizing now — greatly increased my own sense of self, too. My life would be completely different had we not written those characters that way. I don’t think I’ve ever attributed this to the show and to the portrayal of this lead. I wrote myself with more confidence, and now I get to live that out and portray it, too.

“Insecure” is ending in a complicated moment, a year after Black Lives Matter protests ignited the country, and we are still in a pandemic. What do you hope the show’s legacy will be?

ELLIS: There’s security in insecurity. There’s something about the journey that these characters go on by the end of Season 5 that it just feels like, “What happened on Tuesday?” I’m good with what happened Tuesday, and I’m going to keep moving on to Wednesday and not let it ruin my day or my life or whatever.

RAE: I’ve got to credit Amy. We were really trying to find the right way to end the show and she told us, “We keep trying to land the plane.” Instead, she reminded us that the plane ride continues, and these characters are going to live on. That was so freeing to be able to say to each other, “Oh, we’re not ending this show.” These characters that I know and I’ve grown with are going to continue to make decisions and live on.