'Insecure' Will End with Season 5 and We're Lowkey Devastated

Erica Gonzales, Bianca Betancourt
·6 min read
'Insecure' Will End with Season 5 and We're Lowkey Devastated

From Harper's BAZAAR

Insecure offered some much-needed pleasures in 2020. But with its 10-episode fourth season now drawn to a close, the Emmy-nominated HBO series from Issa Rae and Larry Wilmore will be dearly missed. What's to come next of Issa and Molly's friendship, or Issa and Lawrence's love after that bombshell reveal? We may have to wait until Season 5 to find out. Here's what we know about the upcoming installment so far.

Season 5 will be the show's last.

In heartbreaking news, HBO confirmed that Insecure will end with its fifth season.

Issa Rae also addressed the show's ending to Deadline. "Prentice [Penny] and I are so grateful that HBO believed in our show from the beginning and kept faith in us to see our vision through the end,” she said. “We always planned to tell this story through five seasons, but we couldn’t have made it this far without the tremendous support of our audience. I feel blessed beyond measure to bring our characters’ stories to an end, on-screen at least.”

It will be released later in 2021.

HBO Max confirmed in a new video that Insecure's new season would be arriving in 2021. While announcing the fate of Season 5, the network confirmed production would begin in late January and the final installment would be released later in the year.

Rae teased to Variety that Insecure is expected to return in 2021, and filming was set to begin in November 2020 ("six months from now," she said in mid-May), but given the pandemic, the schedule has understandably changed.

“And so, in short, I guess it depends on where we are, you know, six months from now when we shoot,” she said. “Obviously we have a schedule where we’re supposed to shoot, but who knows if we’re going to meet that. Who knows if we’re even going to be able to come out next year, so there’s just so many ‘if’ factors.”

Season 5 was confirmed in May 2020.

HBO announced the news on May 1, just weeks into Season 4.

“We’re thrilled that Issa, Prentice [Penny, producer], and the whole Insecure team will be getting back together for a fifth season,” Amy Gravitt, executive vice president of HBO Programming, said in a statement at the time. “As we laugh and cringe with recognition, their stories make us all feel a little less alone in the world.”

When the announcement dropped, stars like Rae, Jay Ellis (Lawrence), and Yvonne Orji (Molly) celebrated the news on social media. "Grateful to officially come back for Season 5!" Rae tweeted with a clip of the series.

It was written during quarantine.

On May 4, Rae shared a photo of the Insecure writers "back to work" for the fifth season, congregating via video chat. Some of the attendees included the star and co-creator herself, producer Prentice Penny, and star/writer/producer/director Natasha Rothwell (Kelli).

Speaking to Variety, Rae said "it feels really good to be back" working with the Insecure team, even if it's virtually. "And it’s like my only social interaction right now is just the weird virtual writer’s room. So that part is really exciting."

Rae and the rest of the cast have started table reads again—via Zoom.

Issa Rae shared on Instagram the first glimpse of the cast coming back together for season five with of course, a virtual table reading via Zoom. In the photo the script for the first episode of the show's fifth season can be seen with members of the cast in their respective Zoom tiles on Rae's computer screen.

"Season 5 Table Read. Different. #insecurehbo," wrote Rae.

But don't get your hopes up for a socially distanced episode.

When asked if she'd include social distancing culture or shelter-in-place practices in the upcoming season, Rae wasn't crazy about the idea.

"I already have fatigue of it because we’re living it and I think that’s my biggest worry is just, you know, I don’t want the show to feel dated and obviously certain aspects will already feel dated by nature,” she also told Variety. “I think there might be a world where we acknowledge it in the background, because I think it obviously will have long-lasting impacts."

Rae added that she didn't want to overlook how the pandemic has affected the Black community. "But one of the saddest things is seeing how it’s affecting my favorite restaurants in South L.A., my favorite Black businesses are being impacted and having to close shop, and so we don’t want to feel tone-deaf in ignoring it," she continued. "We’ve always taken pride in representing the city as is."

Photo credit: HBO
Photo credit: HBO

Issa and Molly's friendship won't be the same.

In the final moments of the Season 4 finale—spoiler alert!—Issa and Molly finally meet up for a long-overdue sit-down, one that came after weeks of high tensions and frustrating arguments. But that doesn't mean their broken friendship will be completely mended come next season. The writers "don't want them to go back to where they were," showrunner and director Prentice Penny told Entertainment Weekly about crafting Season 5.

"They're going to be forever changed by this, forever humbled by this, and hopefully, forever close by this. I don't think it's about getting them back to where they were. I think we're always going to have a version of them having fun together because they're friends, but I think we want to explore what is that road back like and how is that road different."

Penny later added of the duo's new dynamic, "I think we're trying to let them be like a 2.0 version of themselves."

Photo credit: HBO
Photo credit: HBO

We'll have to wait and see whether Lawrence and Issa are still together.

When asked whether Issa and Lawrence's final joint scene—after he reveals that his ex, Condola, is pregnant with his child—was supposed to be read as a breakup scene, Penny played coy. "I mean, you have to wait until season 5. Where's the fun in that?" He also explained that that scene was intentionally vague and up for interpretation.

There could be more of Issa and Nathan.

"I think we're trying one of the questions that's still sort of hanging from this: The Issa-Lawrence Issa-Nathan [relationships]," Penny teased of Season 5 to EW. He added that other potential themes include whether Issa finds professional success, where her friendship with Molly stands, and whether Molly can find love.

"Really, the thing we're playing with is, again: If life doesn't look like how you imagined it, does that mean it's a success or a failure?" Penny said.

Watch this space for updates.

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