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After five seasons and 44 episodes, Insecure has come to an end. Issa Rae’s groundbreaking HBO series about two friends Issa and Molly (Yvonne Orji), navigating the ups and downs of adulting in South Los Angeles, saw each of them come out on the other side more confident, more mature and much more self-assure. “I mean, this is a journey of growth,” Rae tells ET about her character’s onscreen evolution. “So, if Issa’s in the same place as she was in season 1, then we failed.”
That said, the ending was also a satisfying one despite notions that not all fans would be happy with where things ended up. While speaking with ET, showrunner Prentice Penny and the cast, including Orji, Jay Ellis and others, talk about getting to close out the series on their own terms, and their emotional final days on set.
“Like most TV shows, not everybody is gonna get what they want,” says Leonard Robinson (Taurean Jackson), before adding that when it comes to the finale, “[we got] what the characters deserved and what they wanted, which is a great, satisfying ending.”
He adds, “It all came to a proper ending.”
In “Everything Gonna Be, Okay?!,” written by Rae and directed by Penny, Issa reflects on everything it took to get where she is today as the episodes jumps forward through time to show where she, Molly (and Taurean), Kelli, Tiffany and Lawrence (and Condola, played by Christina Elmore) have all ended up.
Noticeably absent from that list is Nathan (Kendrick Sampson), who is last seen at the beginning of the episode needing some space. At that point, it becomes quite clear he and Issa are not meant to last. And it’s not until Issa’s surprise birthday party that we find out he’s in a better place – without her.
Then, as the episode continues to jump from birthday to birthday, we find out more about the ups and downs of everyone’s life:
Tiffany is still in Denver with Derek (Wade Allain-Marcus) even though she’s having a hard time adjusting to the move. We find out later that she’s pregnant with her and Derek’s second baby.
Kelli falls in love with a named Desmond (after rebounding from her imaginary fling with Daniel Kaluuya) before eventually announcing that they're having a child together. She also joins Molly’s firm.
While Molly’s mother unexpectedly dies, she continues to move forward. And that includes getting married to Taurean in a lavish Italian wedding. And despite their friendship’s ebbs and flows, Issa, Kelli and Tiffany are all there as bridesmaids. We last see Molly checking in on Issa from her sex-filled honeymoon in Greece.
While Lawrence's parents like Condola, the two never get back together – but seem committed to co-parenting Elijah. He’s seen dating a few women before arriving at Issa’s new office for The Blocc many years later. And in that time Issa was also seen dating a few men. But clearly Lawrence was always on the back of her mind. After reuniting, they decide they’re finally ready to find out if they’ll actually work out this time around. A year later, the two are seen happily in love as they attend Molly’s wedding.
And while Issa and Lawrence have finally ended up on the same page, it’s where things end up between Molly and Issa that matter most. And it’s at the end of Molly’s wedding, when Issa is helping her out of her dress, that the two have a heart to heart about their friendship.
“Thank you for everything. For just being you, and loving me... and girl, I don’t know where things are going to take us, but as long as you’re around, I’m goin’ to be okay,” Molly tearfully tells Issa, who replies, “Yeah, you too.”
“I love you,” they both say to each other as they hug it out. And we see that despite all their ups and downs, these two are for life.
When it comes to how the series ends, and where things end up for Lawrence in particular, Ellis recalls “feeling very full and content and very happy.”
“I remember having that feeling -- and it's bittersweet -- but at the same time, it also felt like, ‘Yeah, this is how we’re supposed to be. This is what it's supposed to feel like. And this is the way this story’s supposed to end,’” he continues, before revealing how he and the entire cast and crew were in tears after their final table read together. “Issa was the last one to hold out. And then, once she saw a room of 50 people literally wiping snot from their noses she was like, ‘Okay, I can’t hold these back anymore.’ Then she got up and she made this really beautiful speech about what the show has meant to her.”
Also in tears was Orji, who remembers sharing a moment with Ellis and Rae at the table read as they all got emotional. “There was no tug in me left,” she says, noting how special it was for everyone to finally be in a room together one final time after COVID had separated them all for so long. “It was like, ‘Oh, my god. It’s the last time we’ll be in this room,’” she adds. “For us to be in a big soundstage... just being there one last time, I think is the culmination of the moment.”
How fans react to the final chapter in the five-season journey of Insecure remains to be seen (“The only way that most of the Insecure fans would be, myself included, is if the show goes on forever,” Elmore quips), but what matters most to Rae, Penny and the rest of the team, is that they got to end the series on their own terms.
“It’s not like these characters lives are ending,” Penny says, explaining that their stories continue. “It's just that the audience and the writers aren’t continuing with them on their journey. But they’re going to still go on and live lives, theoretically.”
And knowing that, he says that “really freed us up to not worry about the perfect ending.”
“You know, it’s not often that a TV show gets to choose when they want to end. And so, we had a great time with season 5 and it was all planned,” Sujata Day (Sarah) says.
“The truth is, they concluded the show the way they wanted to,” Allain-Marcus says of Rae, Penny and the rest of the creative team. “We brought everything that we could into this last season.”
He adds, “In the end, this was a final gift to [the fans].”
--Additional reporting by Denny Directo and Liz Calvario