HBO's 'Insecure' soars by staying true to its revolutionary mission

Oct 25, 2021
Originally published on October 25, 2021 10:11 am

(Be warned: A few mild spoilers emerge below regarding Insecure's fifth season.)

Five years ago, I sat in a Los Angeles hotel meeting room with Insecure's creator/star Issa Rae, talking about how her new series was going to feel like a TV revolution because it focused on "basic" – her words – Black people, especially Black women, trying to make their way in life.

"Isn't it sad that it's revolutionary?" Rae told me back then. "We don't get to just have a show about regular Black people being basic."

As the show's final season debuts on HBO, it's obvious just how prophetic those words were. The start of Insecure's fifth season is poignant, entertaining, insightful, ambitious and hilarious, even as it features a crew of characters we've seen evolve for years, still fumbling their way through work and relationships while trying to find some sense of satisfaction.

And after watching four episodes from the new season, it's also obvious that the program's power is still rooted in its focus on authentic characters going about life: dating, rethinking friendships, parenting and hanging out.

Issa Rae and Yvonne Orji play friends Issa and Molly on HBO's 'Insecure.'
Raymond Liu / HBO

These aren't super-famous super women or particularly traumatized people. They make each other laugh and tell stupid jokes one moment, before making the kind of head-scratching choices that bring drama and confusion.

It's Black joy and pain and struggle without the typical storytelling cliches; race only matters when it needs to, yet Black culture underlines every aspect. And it works as well as ever in this final season.

Finding joy and drama in everyday life

Case in point: in the first episode of the new season, Issa (yes, Rae's character shares her first name) has joined her friends in a reunion at Stanford University, back on the campus after 10 years. She's even appearing on a panel of other alums who have started businesses – there's a great moment where she has one of her trademark bathroom conversations with a reflection of her old self from college – and can't help over-enthusiastically greeting most everyone she comes across.

"We can all tell who you can't remember by the tone of your, 'Hey!'" one friend tells Issa, just before she does it again. Anyone who has ever been at a conference or school reunion can relate – often, the volume and energy of your greeting is directly proportional to how little you remember the person you're hailing.

Like many of Insecure's best moments, the most hilarious scenes come when Issa's awkwardness takes center stage. Consider her reaction during that alumni panel, where Issa is the only one to acknowledge she's not sure of her current path: "Maybe I'll wake up tomorrow and realize that I wasted all my time," she says to a bewildered audience.

Of course, Issa delivers next-level awkwardness in her interactions with Yvonne Orji's Molly, once her ride-or-die best friend. As the new episode opens, they are still tip-toeing around each other at the reunion like estranged lovers who can't quite let go – it's the culmination of a schism which had been developing throughout last season.

The question of what will happen to their friendship is the best will-they-or-won't-they story of the show's run. Issa and Molly may fall in and out of romance with any number of men. But their bond to each other is often the core of the series and seeing that tested is more interesting than any other relationship agita here.

Even on a campus like Stanford's where African Americans are seriously outnumbered, the space Insecure creates is unapologetically and effortlessly Black — as Issa, Molly and Natasha Rothwell's scene stealing Kelli reunite with an old college friend who winds up being a bit more than they bargained for. (I can't write more without dropping a major-ish spoiler). The way that connection ends is a prime example of how the show can dip into a scene that is steeped in Blackness, and then turn back to storytelling ground that is more universal.

Most intriguing of all, this first episode seems to be about looking around and realizing that you've grown – or desperately want to grow – and that growth requires making different choices. Even when that choice hurts, or you're not quite sure where it will lead you.

Culturally specific, yet universally appealing

Ultimately, Insecure gives us a set of characters and a story that remains compelling five seasons in, balancing sidesplitting jokes and knowing asides with dramatic moments where people try to speak honestly about what they want and where they stand. As someone who is a few years past these characters' ages, it feels like a letter-perfect rendition of the uncertainty and searching that can fill your thirtysomething days, as you rack up the kinds of mistakes and experiences that also can lead you to a better, truer life.

It's also an example of how something that's culturally specific can also tell a universal story. Insecure zeroes in on the voice of Black millennials – in one moment, Issa is texting Molly while they're both inside the same car, which could not feel more millennial. It's a scene that feels unique because of the people it's portraying, while also providing a universal story lots of different viewers can relate to.

That's why it's sad to read media reports where Rae says she was advised to add white characters to her work, back when she was creating the groundbreaking web series The Mis-Adventures of Awkward Black Girl, which debuted in 2011. According to a story in Mic, a colleague told her white characters would make white people care about the show, which would make NPR write about it.

"And then it literally happened," Rae says in the Mic story, seemingly referring to a 2011 interview with NPR anchor Michel Martin. For the record, I don't think Martin or I cared much about white characters when we did our stories on Rae's work. But I understand the pressure Black creators faced from a TV industry nervous that white viewers wouldn't see themselves in Black characters — even though Black viewers have been forced to see themselves in white characters for many years.

When we spoke back in the day, Rae was making history as the first Black woman to create and star in a series for HBO. There was a sense that she, along with Donald Glover on FX's Atlanta, was part a of new generation of Black storytellers insisting on new ways to center Black people and culture on television shows.

These days, there are many more TV shows centered on groups of Black female friends which feel like distant cousins to Insecure, including ABC's Queens, Starz's Run the World and BET's Sistas, First Wives Club and Twenties. HBO has garnered acclaim and awards for other shows created by and starring Black women: Robin Thede's A Black Lady Sketch Show and Michaela Coel's I May Destroy You.

Rae herself has matured into a mogul of sorts, executive producing programs like A Black Lady Sketch Show, a reboot of Project Greenlight (where she will also serve as mentor to aspiring filmmakers) and HBO Max's upcoming Rap Sh*t, also appearing in movies like Little and The Lovebirds. She's created her own audio company called Raedio and used her production company, Hoorae Media, to consolidate all her media ventures, while scoring a first-look deal with WarnerMedia.

Still, Insecure remains the touchstone of her success; the mothership series where her focus on normalizing the lives of Black people has resonated worldwide.

And the first few episodes of the final season hint that the series will end as it began: Mining funny, emotional, telling stories from the lives of basic characters who turn out to be complicated as any on television.

Copyright 2021 NPR. To see more, visit


HBO's "Insecure" starts its fifth and final season tonight, centered on awkward 30-something Issa Dee and the lives of Black millennials in Los Angeles. In this clip from Sunday's episode, Issa, played by creator and star Issa Rae, is attending a 10-year reunion at Stanford University. And her return to campus is - well, it's awkward.


ISSA RAE: (As Issa Dee) Hey.

UNIDENTIFIED ACTOR #1: (As character) Issa, we can all tell who you can't remember by the tone of your hey.

RAE: (As Issa Dee) Is it that obvious?

UNIDENTIFIED ACTOR #2: (As character) Hey.

RAE: (As Issa Dee) Hey.

UNIDENTIFIED ACTOR #3: (As character) Real smooth, girl.

FOLKENFLIK: Here to talk about the show's return and what it means that the series' run is ending is NPR TV critic Eric Deggans. Hey, Eric.


FOLKENFLIK: So I remember watching Season 1, and Issa Rae's character really popped for me. Why was what she was doing different?

DEGGANS: Well, I think it all goes back to the show's initial approach. Now, I interviewed Issa Rae back in 2016, just before the show debuted, and she told me that at a time when we had these Black-led series that featured women who were political masterminds or high-powered record executives, it felt like a revolution just to create a TV show about average Black millennials.


RAE: We don't get to do that. We don't get to, like, just have a show about regular Black people being basic. I remember, like, even, like, a Black woman that I could, like, relate to and be like, oh, I can relate to her decisions or I can relate to her essence - that didn't happen. I mean, I think "Moesha" was the last show where I remember - oh, this is just a regular Black girl.

DEGGANS: And "Moesha," you might remember, debuted on the now defunct UPN network back in 1996. But Rae said it was a real inspiration for her. She had attended a taping of the show, and she even used one of its scripts as a template for her own writing.

FOLKENFLIK: We got to be careful about spoilers, of course, but you know, you said that the last season ended on something of a cliffhanger. What can you tell us about what happens in this new season?

DEGGANS: So fans know that the friendship at the heart of this show between Issa Dee and her one-time best friend, the perfectionist lawyer Molly, who's played by Yvonne Orji, has been strained all through last season. And as the new season opens, they're tiptoeing around each other at the Stanford reunion. They're trying to figure out where their friendship stands. And I thought that was, like, a great creative choice because one of the strengths of "Insecure" is its authentic depiction of friendships among Black women. So to see the core relationship kind of tested as the two women grow and they start to ask these really serious questions about the choices they're making in life, it feels like a great sort of allegory for how the show has grown up, too.

So in the fifth season, "Insecure" is staying true to its original focus. It's showing Issa and her friends negotiating romances and career choices and friendships. It's just a pleasure to see Black characters that aren't always rooted in trauma or pain negotiating lives that look a lot like the real world.

FOLKENFLIK: It seems as if TV networks and streaming services have gotten a lot less worried about whether white audiences will watch shows with mostly Black characters. How does "Insecure's" success play into that?

DEGGANS: Well, I think it's one of the series that helped make the case that something like that could work. I mean, in a recent interview, Rae said that she was advised to put white characters in this web series that she created in 2011 called "The Misadventures Of Awkward Black Girl" because that would make white people care, and then NPR would do a story, and it would take off. And in 2011, NPR did do a story. Michel Martin talked to her. But I don't think it was about the show's white characters. You know, we have all learned, I think, that when TV creators make a show that's culturally authentic, it feels different, but it's also communicating these universal human truths. And I think that's what's happened with "Insecure."

FOLKENFLIK: So let's take a moment to talk about Issa Rae herself. She's made a lot of strides, hit a lot of benchmarks as a creator of media, as an executive producer, as an actor. What are some of the big projects she's intending to take on after "Insecure" ends its run?

DEGGANS: She's got a new series on HBO Max called "Rap - you know, it's the curse word we can't say on the radio.


DEGGANS: And she's an executive producer on the HBO comedy series, "A Black Lady Sketch Show," you know, which just finished its second season. And she's putting together a film with Jordan Peele's production company. You know, when Issa Rae first sort of burst onto the scene, I think there was this hope that artists like her would be the vanguard of a growing number of non-white producers, show creators and stars. And I think Issa Rae's journey with "Insecure" seems to be a great example of how that's worked out.

FOLKENFLIK: That's NPR TV critic Eric Deggans. Eric, thanks.

DEGGANS: Always a pleasure. Transcript provided by NPR, Copyright NPR.