The fifth and final season Issa Rae's Insecure proves it's one of TV's best shows, says Kevin Fallon. "It sees the potential for drama in the small blips of life, the choices that may not seem extreme to the outside world but are crippling for the individual—moments of growth, realization, and, perhaps more often than we acknowledge, unchangeable or inevitable circumstance that dictate what our life is going to become," he says. "These things can be ordinary but, in that, they are extreme. That seems to be what Insecure gets. This isn’t necessarily a brilliant observation about the series." Fallon adds: "Few shows are as honest about what it means to be an adult and figure out what romance and love means to you as you reach a new stage of life. Few shows are as blunt—and, in that respect, maybe truthful to the point of being cruel—about what friendship is and what you need from it. Most relatably, few shows reveal with such insight how, on that path that you’re not sure you’re supposed to be on where you’re not really figuring things out, you can be your own worst enemy and saboteur. That can be because of fleeting times when you allow yourself to be selfish or careless or dangerous. The show is truthful about the fact that there’s no safety net for you when that happens. But, metaphorically at least, there is often a trampoline somewhere along that fall, and you have the opportunity to bounce back. Maybe not to the heights you were aiming for at first, but you can be OK with settling where you land. run. It had to be about Black love, Black friendship, and Black excellence, a burden of representation and expectation that is impossible to live up to. It had to be about everybody and for everybody the way they wanted and how they wanted to see it. That’s an impossible mandate. But I think the show realized that it couldn’t juggle everything. And besides, you know who juggles? A clown. It’s a show that knew who Issa is, who Molly and Lawrence and these characters are, and allowed that to guide the way. And as the series went on, it became deeper. It got more cinematic, perhaps the most beautifully framed and shot comedy on TV. And it had the courage to lean into seriousness. Some episodes could have been entered in drama categories at the Emmys, and deserved to win. Now, it’s a show that knows when it’s time to say goodbye, too. More than anything else, that’s growth."
Insecure is the kind of series meant to be experienced but not studied: "Let its joys just wash over you and lull you into submission with its sparkling nature lest you find yourself noticing all the fissures," says Angelica Jade Bastién. "These fissures aren’t the sort of touching imperfections that can make a work all the more rich but are grating blunders on various levels that can curdle the light touch the show is aiming for and often hits. The first four episodes of its final season were made available to critics, and they are for the most part strong and deliciously entertaining. But certain issues linger. The fourth season ended explosively with Lawrence (Jay Ellis) learning his ex-girlfriend Condola (Christina Elmore) is pregnant with his child and wants to become a mother, which casts a pall over his reconciliation with Issa. It’s a cheap narrative move the show is now left to reckon with. All soap operatics, no depth. Blessedly, the new season doesn’t pick up with that specific plotline. Instead, Issa (Issa Rae), Molly (Yvonne Orji), Kelli (Natasha Rothwell), and Tiffany (Amanda Seales) attend their ten-year college reunion at Stanford with Tiffany’s husband (Wade Allain-Marcus) in tow. Set against the splendid beauty of the Bay Area, the first episode illuminates the predominant considerations of the season: Molly and Issa’s efforts to strengthen their friendship after its previous ruptures; Tiffany navigating motherhood and married life; Molly figuring out what she wants romantically after years of fumbles, heartbreak, and high standards that made finding the love she desires tricky; and Issa stumbling through realizations about her own professional standing and romantic entanglements. (Kelli remains humorous, a straight shot of joy, no chaser, against the tangled complications of her compatriots, but she’s still scantly developed.) The strength of the new season, particularly the first two episodes, is in showrunner Prentice Penny and the other writers’ efforts to nudge the characters toward deeper considerations of where they are in life and where they’re going."
Insecure commits to growth in Season 5: "HBO’s Insecure has always been a show about growth," says Radhika Menon. "The excellent Issa Rae vehicle, which she also created with Larry Wilmore, centers on Issa, a former nonprofit employee-turned-entrepreneur who is chasing fulfillment, both personally and professionally. In Season 1, Issa’s feelings of stasis at work and in her relationship led her to lash out and threaten the bedrocks of her life; the aftermath then put her on a rocky path to self-discovery, which is still ongoing. Over the course of four seasons, Issa, her best friend Molly (Yvonne Orji), her on-again off-again boyfriend Lawrence (Jay Ellis), and their circle of romantic interests, friends, and coworkers have evolved from lost and confused young adults to confident, successful people who have made inroads towards achieving their life goals. But as a show about Millennials, Insecure’s final season leans into this generation’s most incisive fear: why do I still feel so far from where I should be? In the four episodes of Season 5 that were provided to critics, the show takes care to illuminate how far the crew has come: Issa is recognized on an entrepreneurship panel at her alma mater, Molly adopts an open attitude towards dating, and Lawrence steps up to fulfill his fatherly duties. All of their previous pitfalls—confidence, open-mindedness, responsibility—seem to have worked themselves out, and they’ve come full circle in their evolution into adulthood. But lurking underneath all of these glow-ups is a part of them that still wonders how they got here and why they feel so (to borrow a term) insecure about their decisions?"
Season 5 affirms Insecure's legacy as an elegant and confident depiction of a specific kind of Black millennial experience: "As with earlier episodes, Insecure opens its final season by deftly balancing its heavier themes with lighter moments," says Lovia Gyarkye. "Issa, Molly, Kelli, Tiffany and Derek (Wade Allain-Marcus) jab and joke while trying to recall former classmates’ names and remarking on (aka judging) the lives of others. A return to campus provides a rich source of material that sharpens our understanding of this friend group. I’d be remiss not to mention the aesthetic choices that have consistently made Insecure a pleasurable viewing experience. The outfits are still magnificent, the lighting remains on point, and the sets are still carefully curated."
Showrunner Prentice Penny on how the lessons of Season 1 propelled Insecure forward: "A lot of the things that we had in the back half of season 1 ended up moving to the front half," he says. "The end of the first season, when we initially broke it, was Issa sleeping with Daniel (Y'lan Noel). (HBO) was like, 'No, no, no, make that happen in the middle.' We were like, 'But what do we have for the end?' 'You'll figure it out.' They were right. That was the most interesting stuff, and we were kind of stalling the story. It was just a good thing to know — 'No, no, no, just keep pinning yourself into a corner and figuring out how to get out of there.' The other lesson we learned early on was anything that got a strong debate in the writers' room, that's going in the show."
Issa Rae recalls almost dropping Jay Ellis' Lawrence after Season 1: She compares the decision to keep Lawrence around to the Breaking Bad team forgoing their plans to kill off Jesse Pinkman because of Aaron Paul's performance. "In my mind in season 1, I didn't know that he would last so long," says Rae. "But Jay brought so much humanity (to Lawrence) and made him so endearing, but also personable and relatable — where everyone knows a guy like that. Those were the stories that were interesting to write, specifically because there weren't a lot of examples on screen of just a regular Black dude who's not cool, not extraordinary. He's just a dude trying to figure it out, too."
Issa Rae agrees that Insecure's most revolutionary aspect was the abundance of decidedly unsexy moments: “True representation is the ability to show your vulnerability and be able to say, ‘I don’t have it all together, just like the next white person doesn’t have it all together,’” Rae says of depicting the kinds of mistakes young adults make. “I think the show gave Black people permission to also be like, ‘You’re right: We are insecure.’” In making Insecure, Rae had the goal of depicting “just regular Black people living life.” "I think we nailed it," says Rae. "The goal was to elevate regular Black people and make us look as beautiful in our regularness as humanly possible. I think we achieved that." Showrunner Prentice Penny adds: "One of the problems we show is that Black people face racial microaggressions at random. Like, in Episode 3 of the first season, when Issa Dee realized that her white co-workers were leaving her out of their emails. Not everybody’s shot by the police, but everybody knows what it feels like when white people are talking about you behind your back. Those are the things that felt regular, right? Or what is life like for a Black person on any given Tuesday? A day that’s not special, but super regular. That was our North Star."