The 'Insecure' Final Season Trailer Is Making Us Emotional

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 premieres October 24.

HBO has dropped the first teaser for the show's final season, along with its release date, October 24. The sentimental clip flashes through Issa's bathroom mirror pep talks and confessionals over the seasons, with her voice saying in the background, "I just wanna be drama free and happy." She also admits that she is "terrified" of what happens next.

The official trailer shows the cast going through growing pains.

Issa appears to be navigating life without Lawrence, Molly adjusts to reentering single life, Tiffany embraces motherhood, and Lawrence is looking emo and sad. Oh, and Condola had her baby. Watch the official trailer for the final season, below.

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."

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."

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.

They have already started filming.

On January 21, Rae shared a selfie video showing her Season 5 trailer. "First Day of Season Bye-ve," she wrote in a punny caption.

She also shared a BTS video with costar Orji.

Kerry Washington is returning to direct.

Washington will helm Insecure's Season 5, Episode 5, which was written by Laura Kittrell, the Scandal star announced in an Instagram video. The actor-director shared the news with a clip of Rae and Orji discussing the last time she directed an Insecure episode, which was for Season 4.

"Kerry was like, 'I just want to let you know, if I don't feel it, I'm gonna call you out,'" Orji recalled in the video. "I was like, 'I hope you feel it!' She didn't feel it."

"She's not playing," Rae responded with a laugh.

Playing along, Washington wrote in the caption of her video, "Season 5 🎬. Still not playin....😂"

Rae is most excited for Molly's Season 5 storyline.

After speaking exclusively with the Insecure star and creator, People reported that Rae "says she's most excited for people to watch Molly's character development throughout the final season, but won't spoil any details."

Though she didn't share intel about Molly's Season 5 arc, she did share how the pandemic would affect all the characters in the final episodes. "They're asking themselves, 'Are we going to be okay?' Because so much happened last season in their lives," she told People. "We thought they would be faced with this question of despair, and that question will motivate them throughout the season."

The last three episodes will feel like a "triptych."

The final three episodes of the series "should feel like a cohesive triptych," Vanity Fair reports in Issa Rae's cover story. That's proving to be a challenge, however, because the crew is not filming the episodes in order.

The finale was not yet written at the time of Rae's interview for the magazine, but the Insecure creator had shared a "long, passionate letter" to showrunner Prentice Penny and writer Amy Aniobi about her vision for the series' ending.

"Came up with an idea I’m really excited about that consolidates some of the ideas that have been brewing for us… I was thinking of my own life and some of my long-term and long-distance friendships—and thinking of the reasons to gather our girls, that feel central to our show...." Rae wrote.

The cast is wrapping up filming.

Cast members such as Yvonne Orji and, of course, creator and star Issa Rae began to share their goodbyes to Insecure on social media as the show wrapped up filming around June 11.

Orji shared a sentimental Instagram post featuring a series of video clips and snapshots from her final day of filming and penned an ode to Issa Rae and showrunner, Prentice Penny.

"Last night we said goodbye and God Bless to, not only Molly, but also to our fearless leader, @the_a_prentice. We cried a river, group-hugged, ate cake & popped multiple bottles," wrote Orji. "I’m gon’ miss the heck outta these beautiful people. This wasn’t just a show with some co-stars that I HAD to work with. This was a family that I was privileged to grow with, learn from, and do life with. As we each move on to other projects, we know that we’ll always have this moment, this experience, these last 6 years. What a blessing. WHAT. A. MUTHA. EFFIN. BLESSING."

Issa Rae also shared behind-the-scenes images ahead of her final day of filming to her Instagram stories, and gave a special shoutout to her onscreen best friend for all of her support throughout the years.

"I know that I'll never have a co-star as generous [or] as beautiful as you, wrote Rae alongside a photo of themselves. "Thank you for holding me and us down for 6 years. I LOVE YOU FOREVER @yvonneorji"

Rae also shared a photo featuring Ellis, Penny, and Orji standing side by side with the caption, "Family."

The actress also shared a set of her photos on Twitter:

Penny also shared a post on Instagram as a tribute to the end of the series.

"Hella Over. ❤️🥲," he wrote in the post's caption. "The way #insecurehbo changed my life is too incredible to sum up in a post. All I can say is I’m so thankful and grateful to my sister @issarae for trusting me with her baby. All of my love and gratitude for the other third of #3thehardway @msmelina. To my OG’s @yvonneorji @jayrellis making this little bitty show in Inglewood back in 2015 none of us had any idea, but we all fell in love with with each other immediately. To the backbones of the show @msdeniese and @jonathanberry100 I can’t thank you enough for welcoming me into the fold. Thank you to Casey and @nortivarg for giving me an opportunity to be a part of this amazing show. Thank you to @jimkleverweis who made this happen every day - literally. To all my writers, directors, cast and crew that ever worked on the show, I truly appreciate every thing you poured into it. To my amazing wife @mz_money_penny and my three children I can’t thank you enough for understanding and being patient through all of the sacrifices. I can only hope one day you look back proudly that your husband and father tried to do something positive for the culture. And to the culture, just know everything I did was because I love you. Thank you and good night."

The show's fifth and final season will air in October.

The end of an era is among us. The official Twitter account for Insecure tweeted that the show's final season will premiere in October.

"The wait is almost over. The final season. October," the tweet, which was accompanied by a new image of the show's star, Issa Rae, read.

Rae also took to Twitter to assure fans that a sneak peek of the upcoming season is on the way.

"Chillchillchill we're editing the finale," Rae wrote in response to a fan asking about the whereabouts of the new episodes. "Y'all gone see a little something soon. In the meantime, check out my nieces and nephews on @SweetLifeonMax."

Watch this space for updates.

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