Insecure Season 5: Everything We Know

Fashion

Insecure is set to return with more mirror raps, polarizing love triangles, and awkward moments. But unfortunately, all good things must come to an end—HBO announced that season 5 will be the show’s last.

lawrence and issa insecure

Lawrence and Issa

Courtesy of NetflixNetflix

Insecure‘s season 4 finale ended with a jaw-dropping cliffhanger. In an unexpected twist, Issa (Issa Rae) must decide if her relationship with Lawrence (Jay Ellis) is worth fighting for as he finds out his ex-girlfriend is pregnant. The season also ended with Molly (Yvonne Orji) and Andrew (Alexander Hodge) breaking up. As Issa and Molly hit rock bottom in their relationships, they realize how much they need each other—meeting at a diner to (hopefully) reconcile. But have they reached the point of no return?

Here is everything we know about the upcoming final season of Insecure.

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The series will end with season 5.

HBO announced that Insecure would end after season 5. Amy Gravitt, the network’s executive vice president of programming, told Variety, “The show is as incisive as it is heartfelt, and it has resonated strongly with its audience because of the deeply personal work that Issa, Prentice, Melina, the cast, and the writers have put into it. This talented team has conceived a brilliant final season for Insecure, and we look forward to having many more stories to tell with this singular group of collaborators.”

At the 2021 NAACP Image Awards, Rae took home the Outstanding Actress in a Comedy Series for Insecure. After winning, Rae spoke to Entertainment Tonight about preparing to end the show. “I’ve been wrapping my head around this since, candidly, season 3,” the actress said. “But I’m so grateful to be able to play this character, who is obviously a version of me, and in the same way that I want this character to grow, I want to be able to grow too. So I think that’s what comes with it—I’ve played her for a long time, and I have so much more that I want to do.”

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The trailers are here.

On September 2, HBO shared a first look at Insecure‘s final season, sharing a sentimental trailer that traces the journey of Issa’s mirror pep talks and her onscreen alter ego, Mirror Bitch. “One last time for a little reflection,” the preview reads.

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Then, on September 29, Rae shared a full-length trailer—sadly, for the last time.

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The cast and crew finished filming season 5 in June.

On June 12, Rae posted a gallery of photos with the Insecure crew celebrating the end of the show: “WRAPPED a show I’ve been writing for eight years and shooting for 6, surrounded by a chosen family of incredible creatives.”

According to Rae’s Instagram, season 5 was first in production in January. She posted on Jan. 23: “First Day of Season Bye-ve #InsecureHBO.”

The majority of season 4’s cast will likely return.

The core cast will return for the final season. The girl gang—Issa as Rae, Orji as Molly, Natasha Rothwell as Kelli, and Amanda Seales as Tiffany—posted photos on set, along with Jay Ellis, who plays Lawrence.

molly and issa walking in la

Molly and Issa walking in LA.

Courtesy of NetflixNetflix

According to Popsugar, Nathan (Kendrick Sampson) is also coming back. In season 4, Issa friend-zoned Nathan after reconciling with Lawrence. But even though Issa and Lawrence reunited, Nathan still wants to be with Issa, and the season finale left things unclear about the future of Issa and Nathan’s relationship. On Feb. 11, fans got a tease of what to expect in the last season as paparazzi photographed Issa and Nathan cuddling on a city bench, sharing a laugh.

Season 5 is set to premiere in October.

The first episode of the final season airs on HBO on Sunday, October 24, from 10 to 10:30 P.M. ET/PT. The ensuing episodes will arrive weekly and will also be available to stream on HBO Max, with 10 episodes in total.

HBO announced that season 5 of Insecure would air later this year in HBO Max’s lineup trailer back in December 2020. This summer, the show also confirmed that season 5 would be due in October. “The wait is almost over the final season. October 💜,” the post reads. Rae also previously confirmed to ET that fans would get more than eight episodes.

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Rae wrote season 5 during quarantine.

Rae kept herself busy in lockdown as she spent her days working on the season 5 script. On the Variety After-Show in May 2020, Rae talked about her experience planning the final season virtually. “I think we have a really good room where people are very, like, sensitive to people speaking,” she said. “We implemented a hand-raising policy just because. That’s the other hard part, like we’re such a jokey room, and it is hard to get in there with the jokes. So we’re finding our rhythm, but it’s still really fun.”

Kerry Washington will be in the director’s chair again.

Washington is not a new face to the Insecure crew: She joined the family in season 4 and directed the “Lowkey Trying” episode, which won an Emmy for Outstanding Single-Camera Picture Editing For A Comedy Series. As the episode aired, Washington live-tweeted with fans about the episode. She said it was her dream job and that she’s been a fan of the show for years.

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The Little Fires Everywhere star will take the director’s seat for another episode for season 5. She announced her return in an Instagram video featuring a Instagram Live snippet of Rae and Orji sharing their experience working with her. As the snippet fades out, Washington appears in the video with her directing credit on the cover of the episode five script as “Without Me” by Eminem plays in the background.

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As Rae prepares to turn the page on a significant chapter in her life, she has more projects on the way after signing a five-year deal with WarnerMedia. Rae is currently working on a new series called “Rap Sh*t” that follows two rappers living in Miami, an adaption of Brit Bennett’s bestseller The Vanishing Half, and more that will be featured on HBO and HBO Max.

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