As ‘Insecure’ ends, its heroes -- and its creator -- are still flawed, but now secure

Two women smile and clink glasses in a toast.
Issa Dee, played by writer-creator Issa Rae, right, and her best friend, Molly (Yvonne Orji), find contentment at the end of “Insecure.
(Glen Wilson / HBO)

“Insecure” star-creator Issa Rae always pictured a happy ending for her HBO dramedy. After all, her Issa Dee character and her best friend, Molly (Yvonne Orji), surely deserved some measure of contentment after powering through four seasons of rash decisions, hurt feelings, breakups and confusion. “I decided to approach this season like a romantic comedy,” Rae says, speaking via Zoom from Los Angeles. “If you think of the romantic comedy formula — guy meets girl, guy loses girl, guy tries to win girl back — whatever those iterations are, I wanted to think about those structures within Issa and Molly’s friendship, reminding the characters why they loved each other and needed each other. That permeated the season.”

Even as Issa Dee patched things up with Molly over their long-simmering Season 4 feud, she found herself torn romantically between lovely barbershop owner Nathan (Kendrick Sampson) and soul-mate-in-waiting Lawrence (Jay Ellis). Buoyed by comic relief from hilarious pals Kelli (Natasha Rothwell) and Tiffany (Amanda Seales), “Insecure’s” final season showcased Rae’s quicksilver talents, for which she’s earned her third comedy actress Emmy nomination.

Rae’s first stab at a grand finale imagined Molly and Issa on a “‘Hangover’-ish” holiday in Morocco, but she ditched her fully written script. “It just did not feel right,” Rae says. For one thing, she notes, “most of the episode was not set in L.A., and L.A. has been such a huge part of our show.” Rae retooled the episode, now taking place mainly in South L.A., as a fast-forwarding string of happy birthdays and one tear-splashed wedding when Molly marries fellow lawyer Taureen (Leonard Robinson). “I initially wanted to go straight to Issa and Molly sneaking into the bathroom post-wedding,” Rae says. “But the viewer in me wanted to see them dressed up and having a great time, so I just gave in: ‘Go with the trope, have the big final wedding,’ and I’m glad we did.”


As the sun sets on “Insecure,” Issa Dee celebrates her own birthday with Lawrence, the charming, sometimes maddening boyfriend who fathered a baby with one of Issa’s friends. Rae credits actor Ellis’ natural warmth as key to the couple’s on-screen chemistry. “Jay was immediately so believable and lovable, he became Lawrence. I remember our first major fight when my character’s cheating on him. Being in the scene, I felt like, ‘Damn, I hurt his feelings!’ Jay wasn’t talking to me the entire day. Any time we had scenes together, I’d light up.”

The HBO Max series isn’t flawless, particularly in its attempt to grapple with sexism and the male gaze. But it is always funny, sexy, even moving.

July 21, 2022

Ellis’ character also struck a chord among “Insecure” viewers. Rae, who attended Stanford University before creating her breakthrough YouTube series “Awkward Black Girl,” says, “In many cases, Black men don’t get to be regular guys on television because so often there’s an edge, or a looming death, or a looming arrest, or a looming criminal record. The fact that so many men saw themselves in Lawrence is a testament to Jay’s everyman-ness and also to Prentice Penny, our showrunner, who’s the most empathetic, perfectly sensible person that exists. A lot of Lawrence came from Prentice.”

Although Issa Dee’s personal life often turns messy, the angst rarely lasts long, thanks in large part to former “SNL” writer Rothwell. Originally hired only to write for “Insecure,” Rothwell popped in the room, and Rae invited her to join the cast as irrepressibly naughty accountant Kelli. “My God,” Rae exclaims, “putting Natasha on as a performer was the smartest thing we’ve ever done. From that first day on set, it was just endless jokes, runs, almost like she’s carrying the humor of the show in her pinkie finger.”

However, there wasn’t much to laugh about when Rae and her team started working on Season 5 in the summer of 2020. After George Floyd was killed by police, Rae recalls, “we cried. We were devastated. We were just tired. But ‘Insecure’ was on the air, and here was a show being run by Black people, having mostly people of color in the [writers] room. I’ll never forget thinking about the sense of relief that people could experience by escaping through our show.”

Racism exists as a matter of narrative fact in “Insecure” — Issa Dee runs an events company called BLOcc, short for Black Lives, Opportunities, Culture and Connection — but the characters’ personal lives take precedence over explicit political references. “There’s almost an obligation on some shows that feature Black people to address in quotes, ‘Big Issues,’” Rae says. “With ‘Insecure,’ things manifest themselves in the way you treat your partner or what happens when you go to work. ‘I just had this encounter I don’t know how to deal with and now my boss is asking me something and my head isn’t there and I might f— up the presentation, oh, no!’”

In the series’ closing minutes, Issa Dee takes a contemplative drive past the Sands apartments in Inglewood, where she used to live at the onset of her millennial generation misadventures. Has the self-doubting hero of “Insecure” finally made peace with her insecurities? “We’ve always talked about getting the characters to a place where they’re comfortably uncomfortable,” Rae muses. “Issa Dee’s now very secure about her flaws, and that’s something I deeply relate to.” To bring this realization to life dramatically, Rae says, “I had to ask myself, what would make me happy? As someone who’s lived with these characters for years, where do I want to see them? What do I want? And that’s ultimately what I wrote.”