After five seasons, ‘Insecure’ leaves behind a long-lasting legacy

In the saturated world of television and streaming, “Insecure” has cut through the noise, transcending to levels of cultural sensationalism. And on Sunday — after a five-season run — the show will come to an end.

At its core, “Insecure” is about a group of Black millennials trying to figure life out — their love lives, their friendships, their careers, things to which any young adult can relate. The beauty of the show is, in part, its mundanity. These are regular people, dealing with regular things.

“We feel like we’re watching our friends,” said writer Luvvie Ajayi Jones, who has written recaps of the show since its start in 2016.

Of course, “Insecure” is not the first of its kind. “Julia,” a 1968 NBC sitcom, is notable for being the first show to center a Black woman in a well-rounded role and, around that same time, shows like “The Mary Tyler Moore Show” focused on the life of a single woman trying to work on her career. Though not a sitcom, “Insecure” — in its centering of a Black women friend group — is part of those lineages, said Naeemah Clark, professor of cinema and television arts at Elon University.

But what made “Insecure” so interesting, Clark said, is that it shows the deeper, more holistic connections between Black women. Rae and the team behind the show don’t shy away from showing how Molly (played by Yvonne Orji) felt used in her White law firm, or how Issa felt tokenized and disillusioned at work.

“There’s this understanding of knowledge and support that you don’t get from White friends necessarily. No matter how ‘woke’ the White friends are, it is the other Black women and women of color that understand that navigation,” Clark explained. “And I think ‘Insecure’ did that really well. It relied on the same structure and tropes from shows of the ’60s, ’70s, and ’80s, but there is this element of today’s world, where the Black woman stands culturally.”

These moments are speckled throughout the show’s five seasons. When Lawrence gets pulled over by a police officer. When Issa’s neighborhood becomes increasingly gentrified. When Molly discovers her White male coworkers are making more than her.

“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,'” Prentice Penny, showrunner of “Insecure,” told the New York Times at the start of the fifth season. “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?”

The dealing with it is what “Insecure” showed so well.

“With ‘Insecure,’ there’s something about the everyday-ness and the moments of mundanity and the parts of people’s lives that don’t necessarily spark a sense of spectacle, that can be relatable to audiences,” said Francesca Sobande, lecturer in digital media at Cardiff University.

Shows like “Living Single” in the 1990s and “Girlfriends” in the early 2000s also played in that space — depicting the lives of a group of Black friends. With “Insecure,” though, its platform on HBO offered the opportunity for a different, more nuanced, dive, Clark said.

"Living Single," starring Erika Alexander, Queen Latifah, Kim Fields and Kim Coles aired from 1993 to 1998.

“Issa Rae is not afraid to call a thing a thing, and I think that’s what makes the show watchable,” she explained. “A lot of it is looking at self, figuring out, ‘Who am I, what mistakes did I make?’ Issa is not a perfect character.”

“Insecure” displays that imperfection honestly. In one episode during Season 2, Issa and a colleague attend a predominately Hispanic school to help tutor the kids, but soon realize the Black principal of the school is racist against the Hispanic students and only highlights their services to the other Black kids. At first, Issa brushes off her colleague’s worries that they are participating in that discrimination.

“Sometimes there is a bias in the African American community, too, and she’s shining a light on that (in that episode),” Clark said. “And you very rarely see that.”

Other episodes showed the effects of undiagnosed bipolar disorder on relationships, something Clark said is hardly ever shown on TV, especially with Black characters. It’s this mapping of the previously uncharted that sets “Insecure” apart from its predecessors.

But it’s also, frankly, the quality of the show: the lighting, the writing, the outfits, the soundtrack (Solange Knowles served as a music consultant). All of it made “Insecure” a joy. You wanted to get lost in this South LA world, with its shades of blue and gold set to hip-hop beats. Who wouldn’t?

The digital phenomenon of ‘Insecure’

You can’t talk about the art of “Insecure” without also talking about the significance of Black digital culture. Every Sunday, cast members would tweet and react to the episode right along with the fans — a culture of live-tweeting across living rooms around the world that previously became prominent with “Scandal,” another Black woman-led show. For Black people on Twitter, or just online in general, “Insecure” became an event that was impossible to miss. Regardless of whether someone watched the show or not, many engaged with it, even if only through using Natasha Rothwell’s “growth” GIF.

Before “Insecure,” Rae first rose to fame in 2011 for her web series “The Mis-Adventures of Awkward Black Girl,” in which she starred. It was that show that gave her the footing to create “Insecure.” That’s significant, Sobande said.

She broke it down like this: It is rare for shows starring a dark-skinned Black woman, like Rae, to be created in the first place. On top of that, mainstream media tends to overlook web series and these nontraditional avenues of art and content creation.

All of “Insecure” — from its roots in Rae’s first web series to its current social media prowess — speaks to the elevation and engagement of Black digital culture, Sobande said. And that relationship with Black digital culture is a key part of the show’s legacy.

Rae, who plays Issa Dee in the show, in season 5.

“It’s like the show is in conversation with the audience,” Sobande said.

Sometimes, that conversation is quite literal: Aside from the live-tweeting, costume designer Shiona Turini posts where certain outfits came from after each airing.

And for those who have been watching Rae since her “Mis-Adventures” web series, there’s also a sense of nostalgia, in seeing the ways that both Rae and the media landscape has changed since then. For many of the cast members, their characters on “Insecure” were one of their first major television roles, and members of the team have gone on to be involved in other ways as well. Stars Rothwell and Ellis, for example, made their directorial debuts on the show, as did cinematographer Ava Berkofsky.

“For me, it’s been incredible to witness the journey of the show and also its creators,” Sobande said. “It’s been as exciting to watch that pan out, as it’s been to engage with the show itself.”

What ‘Insecure’ leaves behind

Then there’s the timing of the show, and not just because it aired at a point where social media use is at an all-time high. (Without social media, “Insecure” could have been a very different show, noted Sobande.)

The very first episode of the show aired in October 2016 — at the height of the presidential election in the US. About a month later, in the middle of its first season, President Donald Trump would be elected.

“It was a difficult time for people of color, who felt ‘Oh my gosh, we are in these next four years, there is an administration who doesn’t care about us. Even worse, actually creates problems for us,'” Clark said.

A television show doesn’t change policies or politics , but “Insecure” always framed the Black experience as a valuable one, Clark said. And getting lost in the fluffier plotlines — who should date who, etc — was a nice distraction. That reprieve is part of the show’s legacy, too.

“It was like a little hug on Sunday,” she said.

In her recap of Season 1, Ajayi Jones predicted that the success of “Insecure” would open doors for others down the lane. Looking back now, she says she was right. Because of its success, other shows are filming Black people in more flattering ways than ever, she said, and it debunked the idea that people don’t watch Black stories.

“I think ‘Insecure’ peer-pressured other people to step up their game,” Ajayi Jones said. “I don’t think we’ll know the true depth of ‘Insecure”s impact for a while.”

Still, some of that impact is already perceivable. Ajayi Jones pointed to Amazon Prime’s “Harlem,” as one example — a show that exhibits a similar premise to “Insecure,” while being based in New York. Though not a comedy, Clark used Michaela Coel’s “I May Destroy You” as another example of a Black woman portraying an authentic story, just as “Insecure” did.

Michaela Coel in 'I May Destroy You' also portrays an authentic Black woman-led story, like "Insecure" did, Clark said.

Rae’s impact runs deeper, though. Her journey has shown everyone, but especially young women of color, that they can create art while still being true to themselves, Clark said.

“(Rae) knew who she was. And she knew what she was going to be able to do, and she stuck with it,” Clark said. “I think in that way, it has changed the playing field, it has shown content creators that there isn’t one way to be.”

Still, the success of a show like “Insecure” doesn’t necessarily mean that the media landscape is suddenly democratized, Sobande said. Previous issues that may have stonewalled a show like “Insecure” still exist. Yet the work of Rae and everyone behind “Insecure” can still serve as inspiration, she said.

From a web series, all the way to an Emmy-nominated hit on HBO — this is how far Rae and the “Insecure” team have come. When it ends on December 26, it will be a sad day for many fans — the nostalgia many have and will have for the show is strong, Sobande said.

The promise of “Insecure” means there’s more coming: from Rae, who has signed an estimated $40 million deal with WarnerMedia, and from younger creators following her wave. “Insecure” might be over, but its legacy — its ripples — live on.

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