'Can't believe it's over': Series finale gets emotional goodbyes from HBO's 'Insecure' cast

·5 min read

The unwritten rules of television say Black sitcoms must work to appeal to white viewers and present “respectable” characters, even at the risk of forfeiting authenticity. As the fifth and final season of HBO’s “Insecure” approaches, the cast members and the showrunner are proud to have broken the rules.

Since 2016, “Insecure,” created by and starring Issa Rae, has portrayed flawed characters and highlighted the subtleties of everyday life through both close and strained friendships, passionate romantic relationships and career shifts. It was refreshing to see the quotidian details of Black millennial life when Season One debuted — as well as the multidimensional outfits and natural hairstyles — and it’s that inherent commitment to Blackness that has resonated with viewers over the years, cast members say.

“It does a really good job of showing Black people just in their element,” said Yvonne Orji, who plays Molly, the best friend of Issa Dee (Rae). “I think so often when people write for Black characters, they feel like they've got to add a special sauce to them. It’s so easy to normalize Black people and trauma in every aspect of their lives. The simplicity of this messaging is ‘Yes, Black people suffer trauma ... but we also have to make real-life everyday decisions.’”

The show doesn’t shy away from the very tough issues plaguing the country, however. Last year, Season Four aired as the nation dealt with the start of the coronavirus pandemic and protests after the police killing of George Floyd. In an Instagram post, showrunners acknowledged the unrest and the tone-deafness of promoting a TV show at the time but said they hoped Black viewers would find solace in the show’s “celebration of Black life, love and community.”

This season, set to premiere Sunday, takes place at a different moment. And fans are most likely eager to see what the season will hold for Molly and Issa’s sometimes fraught relationship, as well as Lawrence’s (Jay Ellis) drama with Condola (Christina Elmore). The relationships offer a varied look at even the most intimate areas of life — whether it’s Tiffany’s (Amanda Seales) postpartum depression, Kelli’s (Natasha Rothwell) notoriously casual dating life or Lawrence’s STI. Among such unsexy scenes will undoubtedly be the quintessential awkward and cringe-worthy moments that have come to characterize the comedy-drama.

And with such beloved characters, fans’ allegiances will be reignited until the series’ final moments, Ellis said.

“There’s fingers to point. There’s people to blame,” Ellis said. “There are muddy, murky situations these characters have found themselves in. I don’t know whose side you’ll stand on in all of this. All the ‘hives,’ all the ‘teams,’ are going to be ignited. People are going to be triggered on both sides.”

That’s the beauty of the comedy-drama, Orji said. Even the most endearing characters make bad decisions.

Natasha Rothwell, Yvonne Orji, Issa Rae, Amanda Seales and Wade Allain-Marcus in Season Five of
Natasha Rothwell, Yvonne Orji, Issa Rae, Amanda Seales and Wade Allain-Marcus in Season Five of

“She’s a human being, and she’s complicated and she’s nuanced,” Orji said of Molly. “I think people see themselves in her and they recognize some of their own poor decisions. So often we want to see, especially, Black women be perfect in every way, and then we judge them when they’re not.”

Those imperfections have kept viewers hooked. During each episode, Black social media users flock to the #InsecureHBO hashtag — a reach estimated at 11 million and growing — to hand down judgments, hold thoughtful conversations, share memes and even tell their own stories. To some, a show about two dark-skinned Black women best friends, largely set in South Los Angeles, navigating love lives, friendships and careers isn’t what one would expect to be an HBO hit.

Rae has admitted that, when she was creating the show, a colleague advised her to appeal to white audiences by adding a white character. "Then white people will care about it, then NPR is going to write about your s---, and it’ll blow up,” she said in an interview with Mic.

Rae seemed to take the advice early on by including Freida, Issa’s co-worker at the nonprofit organization We Got Y’all, to serve as a “bridge for white people” before saying goodbye to her when Issa left the job. Writers would go on to prove that a Black TV show isn’t lacking without a white character but is only made more authentic.

“I think Issa and I both feel we left everything on the table,” executive producer Prentice Penny said. “I don’t feel like we ever shortchanged the audience. I don’t feel one ounce of regret, like we could have done this better.

“I just hope that some young filmmakers are looking at the show and go, ‘Wow, telling Black stories in a cinematic way and elevated is possible,’ and I hope it inspires them," Penny said. "I hope the legacy is more inspiration for more creators of color.”

Image: Insecure (Glen Wilson / HBO)
Image: Insecure (Glen Wilson / HBO)

As for the show’s legacy, Penny said, that’s for “other people to sort out.” But one thing’s for certain: “Insecure” has already made a cultural impact. And the show’s stars are already dominating their own ventures: Orji has an HBO comedy special, and Ellis is starring in a coming Dave Franco movie. Fans can look forward to Issa’s beloved mirror-rapping and Molly’s stylish wardrobe along with the drama of the show, and cast members say the last season will be honest and provide closure for millions of fans who faithfully delved into the lives of the crew for five years.

As for both the cast members and the minds behind the show, Orji, Ellis and Penny said they are proud of what they built together and the friendships that have blossomed off-screen.

“I can’t believe it’s over,” Ellis said. “We’ve all spent so much time together over the last five years, but it also feels like we just started. I think it’s because we still love each other.”

CORRECTION (Oct. 22, 11:48 a.m. ET): A previous version of this article misquoted Prentice Penny. He said, “I just hope that some young filmmakers are looking at the show and go, ‘Wow, telling Black stories in a cinematic way and elevated is possible.’” He did not say “impossible.”

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