"It’s a bittersweet end," says Taryn Finley. "It’s hard to say farewell to a show that pushed regular Black people to the forefront when Hollywood has erased the multifaceted spectrum of our experiences from its stories time and time again. When Insecure premiered on HBO in 2016, it felt like a long time coming. Rae had amassed a loyal following from her hit YouTube series The Misadventures of Awkward Black Girl and fans waited for years for a follow-up project featuring a Black woman that evoked a similar relatable yet comedic vibe. Television was starved of normal views into Black life. Enter Rae, showrunner Prentice Penny and director Melina Matsoukas’ FUBU approach...In numerous interviews, Rae discussed the damn-near-impossible task of getting these stories told — and the sacrifices she had to make to tell them. HBO took a chance on Rae and Penny, which created a domino effect. They introduced the world to new talent, including Orji, Tristen J. Winger and Jean Elie. They gave new directors like Ellis and Kevin Bray a chance to shine. They made sure Black LA was its own character, represented in a way that Hollywood rarely ever shows it. They put us on to Black designers and businesses, courtesy of costume designers Ayanna James-Kimani and Shiona Turini. They ignited a conversation around artful cinematography and the best ways to use lighting on darker complexions. And they laid a foundation that has opened doors for nonwhite creatives in the industry. The fictional world of Insecure felt like an extension of our own. The conversations Insecure sparked after each episode brought a little more depth and clarity to our own realities. Whether it be about open marriages, ho phases or friendship breakups, watching Insecure has become a communal bonding experience. It also brought joy when we needed it the most, like in the aftermath of George Floyd’s killing in 2020. When protests broke out and the weight of the world collapsed onto Black America’s shoulders, co-star and writer Natasha Rothwell offered some reprieve with the intimate 'Lowkey Happy' episode."
For Insecure's legacy, comparisons to Girls, Sex and the City, Broad City and Girlfriends are inevitable: "But with the exception of Mara Brock Akil's classic, none of those shows captured the ungainly feeling of early adulting and independence without a fallback option or privilege to coast upon like this show does," says Melanie McFarland. "Issa, Molly, Kelli and Tiffany get to be selfish and even pompous at times, but they're also gorgeously vulnerable and prone to make mistakes. Through them Insecure consistently messages that it gets what it's like to be unleashed on the world with little else but your ambitions and realize there's no map, no going back and nobody to catch you when you fall. Now it's dawning on Issa that the search for the right route to happiness and success may never be over. And Molly fears that as they get older, the roads she hasn't traveled may be closed off to her. And it dives into the mess of what all this means with humor and joy, in a way that no other show on TV does as naturally. Mess is a word that comes up constantly in this show – everybody's a little bit messy, or a lot, and everyone else accepts that to be the case. This show helps us to be OK with our mess. That's why we love when it erupts through Kelli's wildness or simmers under Tiffany's glossy, manicured judgment. Their chaos resembles our own psychological clutter."
Insecure has always fit the mold of a sitcom rather than subverted it: "There’s a gratifying rhythm to its recurring shot-list: beautiful food, vibrant murals, Issa in the mirror," says Amanda Whiting. "The finite dynamics of the same half-dozen characters falling in and out with each other deepens storylines even as it limits them. 'If you knew the end was coming, how would you make the most of your time left?' Kelli asks in the premiere episode, winkingly. In Season 5, Insecure leans into its legacy for awkward small talk in place of punch lines and tensions that roil between the lines of every text message. Its charismatic characters progress, inch by inch, in pursuit of grand romantic love and career clout while taking for granted what’s already aspirational about their lives: to be entrenched with people who you know so well. And to be doing it all in Lotusland."
“Reunited, Okay?!” is a premiere that does an excellent job of showing us exactly how Issa and Molly have changed since we last saw them: "The script, penned by Amy Aniobi (who also guest stars in the episode), takes Issa out of her comfort zone of Los Angeles to Stanford," says Ashley Ray-Harris. "There are some gorgeous shots of Tiffany, Derek and Kelli driving up the I-5 to the bay that set up some wonderful tension: have Molly and Issa reunited? Molly’s Instagram captions might point to her reckoning with some dark times, but is it over Andrew or Issa? Issa apparently has her own 'mess,' but even those details are kept in the dark. Is she still with Lawrence? Who knows? Aniobi’s script plays with these reveals at an incredibly satisfying pace. It allows Issa be Issa and that means our first time seeing her this season is when she immediately climbs into the wrong car, as awkward as ever."
Showrunner Prentice Penny: Why we've rejected demands to make Insecure an hour-long comedy: “I just responded to someone today about it,” Penny says with a laugh. “It’s a half-hour comedy! Nobody goes: ‘Oh, man, how come Malcolm in the Middle wasn’t an hour?’ You might call Succession an hourlong comedy because it’s hilarious in the best way; there’s a ton of jokes in that show. But, no, no hour from us. It’s so dope that people love our show like that. But there’s a line between ‘I wish this show was an hour in Season 1’ and then still saying it in Season 5.”
Jay Ellis says Lawrence should be polarizing: "All of the anger and scorn is justifiable," he says. "If you don’t feel that after watching this character, then I haven’t done my job. I think you need to be conflicted because, to your point, what makes him so polarizing is that he’s trying to do good. He’s not intentionally being malicious, he just doesn’t know or isn’t vulnerable enough to ask the people around him about the direction he should be taking or how he should handle a situation. He isn’t out here like, 'Oh, I’m ‘bout to wreck all these women’s lives!' He’s like, 'Yo, I’m trying to be a good dude, but I’m also looking out for me. I think this is how this is supposed to go, so I’m gonna do it' without realizing that, at times, that has ripple effects in other places. So yeah, I’m sure there’s dudes out there like that, but I think if you look at the heart of the characters, that’s part of why he’s so polarizing. I think so many people can see the heart of the character, and I think in his heart, he’s trying to do better. He’s trying to do the right thing and he wants to be with this woman. He realized being a playboy wasn’t for him. He realized there were things out there that he thought he should be doing that were not for him. He’s a serial monogamist: He wants to be in relationships, he wants to be in love. So I think that if you really boil it down to where his heart lies, you realize there’s good in him. So then it becomes: Okay, stop making these dumb ass decisions. Let’s get you on the right road to being a good person so you’re not hurting other people."
Rae says filming Insecure's final season during the pandemic was "terrible": "You don’t get to socialize in the same way with people. We’re pretty much a tight-knit crew," she says. "Some people I didn’t even recognize. I was like, 'Girl, that’s you? What?' Because their masks will be on. And then, of course, you’re shooting in a dangerous pandemic, so everybody’s anxiety is high. We made the most of it all, but it was really dreadful to be shooting during that time. I have all the respect for the cast and crew who made it happen."