Saying goodbye to Insecure with Issa Rae

Yvonne Orji has been lovingly heckling Issa Rae and Jay Ellis all day. Right now, her two Insecure costars (who play on-again, off-again couple Issa Dee and Lawrence Walker on the hit HBO comedy) are slow dancing and staring romantically into each other’s eyes on the Miami set of their EW digital cover shoot — and Orji is doing all she can to make them crack.

This has been the energy on set all day as the trio, who haven’t seen each other since Rae’s low-key wedding in July, make up for lost time. From cheerleading (“Oh, I see you,” they say at least 10 times each) to poking fun at each other (“Do you guys know any other vowels?” Ellis asks from the wings as Rae and Orji dance and mimic Megan Thee Stallion’s trademark “Ahhhh”), it’s clear these three love nothing more than making each other laugh — especially at their first group photo shoot since EW’s Three Rounds interview in 2017. But something changes as Orji observes Rae and Ellis, who recently wrapped filming on the upcoming fifth and final season (premiering Oct. 22). One moment she’s laughing and then suddenly she gets rather quiet and actually starts to tear up. “It’s so beautiful,” she says, clearly moved by seeing her two friends channel their characters. Those brief tears — not the heckling — finally cause Rae to break and laugh. 

“We wouldn’t be family if we didn’t clown on each other every once in a while,” Orji, who plays the perfection-seeking Molly, later tells EW. “But it is that moment where you see the chemistry and the magic, and you’re like, ‘Oh my gosh, this is ending. This is the last run.’ And I was having that moment of, we should have fun now because this is the last time we will be Issa, Molly, and Lawrence together.”  

It’s easy to see why it’s hard to say goodbye. Insecure is a hyper-specific portrait of Los Angeles life that Rae first began painting on her acclaimed web series The Misadventures of Awkward Black Girl 10 years ago. In 2016 — in collaboration with co-creator Larry Wilmore — Rae transformed those misadventures into her Emmy-nominated series following Issa, an aspiring community organizer trying to figure out her life. Along for the ride are Issa’s best friend Molly, a lawyer with a messy dating life and penchant for self-sabotage, and Issa’s ex-boyfriend/possible soulmate Lawrence, who started out the series unemployed but found his groove in the tech industry following his breakup with Issa. Because it’s HBO, there is a prestige sheen to the show — but beyond that, there’s no high concept or purposefully timely premise, because Insecure believes there’s nothing more interesting than watching these characters simply have brunch, make questionable romantic decisions, walk around Inglewood, and deal with their insecurities. 

“I think the shows where you get to watch people just being excite me,” says Rae, 36, who serves as an executive producer and has received two Emmy nominations for her relatable lead performance (she also received an Outstanding Comedy nod in 2019 as EP). “We always say internally in the room, it’s [about] being Black on a Tuesday. Those are the stories we’re telling.” 

“I didn’t realize at the [beginning] how important a story like this was,” adds Ellis, 39. “It’s like, we don’t want to watch normal life — but once you get into it, you realize that’s important because we need to normalize these things because we don’t see them enough.” 

Orji believes that’s the main reason Insecure has been successful and developed such a passionate (and very vocal) fan base.

“It shows Black people just being Black without any extra sauce,” says the 37-year-old supporting actress Emmy nominee. “So many times when you have a show that centers around Black characters, it’s like, ‘Okay, well what is the plight that they have to overcome? Was it a deadbeat dad? Was it cocaine?’ No, [on Insecure], it was having a degree and still not finding the job you want. That’s also a real-life plight of Black people. It doesn’t have to be so salaciously traumatic. Every day presents a challenge. You don’t have to add any extraness to it. And every day is not only just a challenge, but every day is also fun in some way, shape, or form.”

Insecure challenges what the prevailing culture has come to expect from predominantly Black shows because it’s a show that deals with racism without becoming about racism. Sure, Issa, Molly, and Lawrence face their share of indignities daily — from co-workers sending “secret white emails” doubting your abilities, to learning you make significantly less money than a straight white male at your level, to feeling used after having a threesome with two women who fetishize Black men — but, as in real life, those experiences live (sometimes uncomfortably) beside other mundane aspects of life, like driving for Lyft to make more money, planning a girls’ trip to Coachella, or just going through your ho phase after a breakup. 

“I think about how being stopped by the police for every Black person doesn’t end in death,” says Rae, referencing the season 2 episode “Hella L.A.” — in which Lawrence got pulled over before he wound up in that threesome. “Every racist moment that a Black person experiences doesn’t elicit a day to process it and think about it and live in it. It really is, ‘This microaggression happened or this blatantly racist thing happened to me, but I still have to work. So how does that affect my mindset, or the decision that I make? How does it affect how I talk to my partner?’ That’s just living for us, and it’s not an afterschool-special moment.” 

In the beginning, Rae says, the writers asked themselves three questions while breaking stories: What’s the L.A. of this episode? What’s the gender of this episode? What’s the race of this episode? “That felt like that was a driving factor, thematically, of the kinds of stories we wanted to tell,” she explains. “Then the more and more we dug into these characters’ stories, the less we felt compelled to have themes in that way.” 

It’s important to Rae that people understand she and the writers were crafting these stories based on their own experiences and that the show isn’t trying to represent every single Black person. They want the audience to feel seen, but Rae’s goal has always been to tell a specific story inspired by the people in her life and the South L.A. neighborhood she loves.

“I just think about the old [advice], ‘Write what you know,’ and that is what I know. I know myself, to an extent, and my relationships. And the shows that I’ve loved have a specificity. The shows that I don’t like are targeted towards us, try to teach us a lesson, or group us in a certain category, or tell us what we’re not supposed to be,” says Rae. “It just came down to specificity and not trying to be like, ‘This is the Type A person’ or ‘This is the goofy person who can’t get it together.’ It just really came down to basing it off real people and real experience. Issa is so close to me, and Molly is so close to my best friend.” 

Though Insecure explores relationships of all kinds, Issa and Molly’s friendship is the main axis around which the show revolves — buoyed by a real-life respect established when Rae and Orji first met in 2008, which has blossomed into a sisterhood since they became costars. 

“It’s just that thing where we both really deeply cared about art, humanity, people having chances. When you come [into] a situation with that kind of spirit, it just translates into the work,” says Orji.

Adds Rae: “We were cast as best friends, and we became real friends, very very fast friends.”

The love between them is so real that Orji often found it hard when their characters were at odds. An argument in season 1’s penultimate episode left the actress shaken after the cameras stopped rolling.

“It was so vicious,” she recalls of the moment when the duo exchanged harsh words about their shambolic love lives. “We knew we had so much love for each other. I was so worked up that I had to actually watch back-to-back episodes of Veep to just calm me down when I got home — I needed Selina Meyer to ease me to sleep — because you’re just like, ‘Who are you fighting with? I know you’re talking to Issa, but girl, is there somebody you need to call in real life to get some stuff off your chest?'” 

But that season 1 blowup was nothing compared to where we left Issa and Molly at the end of season 4. As the friends drifted apart, years of uncommunicated issues boiled to the surface, culminating in an explosive falling out between the two that lasted the entire season.

“What really stood out [to the writers] is we hadn’t seen examples of friendship breakups happen on screen, and I’ve experienced it twice. That s— hurts,” says Rae. “You don’t really have the same sympathy or the same knowledge or guidance that you have when a romantic relationship ends. To really dissect the dissolution — the slow dissolution of a friendship — was something that was relatable to a lot of people.” 

Who was at fault for the rift in this case? It depends on who you ask. While the writers aimed to highlight valid pain on both sides, they also didn’t want to make it easy for the audience to choose a team. They hoped viewers would be split, but that was definitely not the case. 

“I was surprised that people had a lot of Molly hate in season 4,” says showrunner Prentice Penny. “We thought the Issa/Molly thing might be a little bit more split down the middle who was mad at who, but it was definitely more 70/30 people more mad at Molly than Issa.” He continues, “What I surmised from it was, Issa is our main character no matter what — and if people have to choose, they’re going to choose the character we’ve been following emotionally for so long.” 

But there is hope for Molly and Issa, who we last saw meeting up for brunch to hash things out in the season 4 finale.

“We start [season 5] in the aftermath of that, and with them figuring out where the relationship actually goes from here and if there is one left,” says Rae.

Orji adds: “Any time you have a rift, it’s always this balancing act of, ‘Are we good?’ or ‘What that mean?’ Every word… every moment feels like something that needs to be processed or analyzed.” 

Issa, Molly, and Lawrence spent the first four seasons searching for satisfaction and stability in their professional and personal lives. That quest becomes even more imperative in the final season, which aims to answer one question: Will they be okay? (To that end, all of season 5’s episode titles end with, “Okay?!”)

“The show is called Insecure, and when you have insecurities, what you’re really saying is, ‘I’m not okay in these areas of my life,'” says Penny. “What we wanted to answer in the last season was, ‘Am I going to be okay if this relationship doesn’t work out? Am I going to be okay if this friendship goes away?’ Sometimes you aren’t dealt the cards you wanted, and then [the question becomes], how do you respond? Can you find a way to be happy? Can you find a way to still thrive?” 

Issa’s relationship with Lawrence also remains up in the air. After breaking up in season 1 and forging their separate paths, the former lovers found their way back to each other in season 4’s Before Sunrise-like eighth episode, “Lowkey Happy,” which saw them go on a dreamy date and rekindle their flame. Unfortunately, the honeymoon period didn’t last long. Lawrence received a job offer in San Francisco and, more importantly, found out his ex-girlfriend Condola was pregnant with his child. As the season ended, Issa was left questioning if she wanted to dive into such a complicated relationship. 

“Issa and Lawrence got to this really great place — and are you really going to let one baby stop a show? Maybe?” says Rae. 

Showstopper or not, becoming a dad allows Lawrence to “come out of his cocoon and be a full butterfly,” says Ellis. “What we’re going to see now is him obviously realizing what it means to be a father [versus] what his vision of being a father was.” 

Ironically, Lawrence wasn’t even supposed to make it this far into the series. “In my mind in season 1, I didn’t know that he would last so long,” says Rae. “But Jay brought so much humanity [to Lawrence] and made him so endearing, but also personable and relatable — where everyone knows a guy like that. Those were the stories that were interesting to write, specifically because there weren’t a lot of examples on screen of just a regular Black dude who’s not cool, not extraordinary. He’s just a dude trying to figure it out, too.” She compares the decision to keep Lawrence around to the Breaking Bad team forgoing their plans to kill off Jesse Pinkman at the end of the AMC drama’s first season after falling in love with actor Aaron Paul’s performance.

“If you asked me, I was Jon Snow. I wasn’t going nowhere. I truly was in my own bubble!” exclaims Ellis, who says he didn’t find out about Lawrence’s original destiny until they were filming season 3. “Had I known that, I don’t think I would have ever phoned it in — because that’s just not who I am — but I’m sure I would have thought about every choice differently. I would have been thinking, ‘Oh, how can I get them to keep me?’ as opposed to just being in it every day. I’m grateful that they waited.” 

While Rae deviated from her Lawrence plan, she held firm on how long Insecure should last. In season 1, Rae and Penny agreed that they only wanted to do five seasons.

“Every show has a DNA,” says Penny. “We always looked at our show as, ‘It isn’t meant to be 90 episodes.’ We never wavered. I think we just felt that’s the right amount of time to tell these characters’ stories.” 

That’s not to say the cast was ready to go their separate ways.

“I retired after Insecure. I think I called it quits,” jokes Orji. “I realize that Insecure and the family we had was such a unique and special experience…. I am still chasing that high.”

Ellis prefers to focus on what’s next for everyone: “Outside of Issa, our entire show has [also] leveled up in a way. Yvonne’s career is insane right now, with specials and hosting and movies. [Consulting producer/star] Natasha Rothwell is doing movies and writing and [signing] deals. There’s [executive producer] Amy Aniobi, and [executive producer] Melina Matsoukas with her movie and big deal. Everyone has had such tremendous success from this show. That, I think, artistically raises the bar in a lot of ways. You can’t put bulls— out. You are challenged to be better every single day because those around you are doing great.” 

That drive to constantly be better was certainly pervasive — particularly heading into the final episode. Two weeks before they were scheduled to start shooting the finale, Rae wrote a lengthy email to Penny, Aniobi, and co-executive producer Laura Kittrell informing them she was unsatisfied with the latest version of the ending.

“Thank God I had a burst of inspiration of what I wanted it to be, and that’s what we ended up shooting. I stand by it, I like it,” Rae says of second-guessing her work. “The other one was good, too, but it just didn’t feel like the most [satisfying]. It didn’t feel like our show,” she continues before acknowledging her, well, insecurities: “I can’t wait to talk about it when it airs to see if I made the wrong decision.”

Motion direction and photography by AB+DM for EW. Studio DP: Geoff George/Neer Motion; Production: Kristen Harding and Alison Wild; Set Design: Chris Darsow/Art Force; Editing: Iyin Landry; Color Correction: Carlos Flores; Post-Production Supervisor: Ethan Bellows; Design: Chuck Kerr. Rae’s Styling: Jason Rembert/Costa Styling; Hair: Nicky B/Texture Management; Makeup: Joanna Simkin/The Wall Group; Manicure: Sherwin Hora/ABTP; Orji’s Styling: Jason Rembert/Costa Styling; Hair: Mary Daniels; Makeup: Joanna Simkin/The Wall Group; Ellis’ Styling: Dan P. Lee; Grooming: Mone’t Howard; Manicure: Andrea Viera/Creative Management.

Family portrait looks: Rae’s Outfit: Thom Browne; Earrings: Jennifer Zeuner; Shoes: Thom Browne; Orji’s Outfit: Thom Browne; Shoes: Versace; Earrings: White Space Jewelry; Ellis’ Suit: Amiri; Shirt: Ralph Lauren; Shoes: AMI; Tie: Stylist’s Own. Character Study looks: Rae’s Outfit: Louis Vuitton; Shoes: Jimmy Choo; Earrings: Sterling King; Orji’s Outfit: Louis Vuitton; Shoes: Louis Vuitton; Earrings: Misho Designs; Ellis’ Outfit: Prada. Mirror looks: Rae’s Fur: Duckie Confetti; Earrings: Chanel; Orji and Ellis’ Fur: Adrienne Landau.