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The 2016 series premiere of Insecure opened with Issa Dee (played endearingly by Issa Rae) standing nervously before a group of fractious students probing her personal life. In the face of invasive questions — “Why do you talk like a white girl?”; “Are you single?”; and “Is this what you always wanted to do?” — Issa strains to maintain her composure. She’s visiting the middle school classroom as a representative of We Got Y’all, an after-school enrichment program run by a white woman with a vague desire to help Black children in the Los Angeles area. It’s by no means the job she wants, but it’s the one she has, and another difficult day leads her to ask, through voiceover, “How different would my life be if I actually went after what I wanted?”
This existential question guided four seasons of the critically acclaimed HBO series, which skillfully chronicles Issa’s life as a 20-something Black professional in Los Angeles. It’s a question that hovered in the back of her mind as she contemplated breaking up with her boyfriend, Lawrence (Jay Ellis), and quitting her job. It loomed over increasingly tense conversations with her best friend, Molly (Yvonne Orji), which culminated in a painful split in the fourth season. It even influenced the arcs of other characters, humanizing the usually pretentious Tiffany (Amanda Seales) and developing the criminally underutilized and quick-witted Kelli (Natasha Rothwell). Going after what you want eventually became the show’s discreet refrain.
Airdate: Sunday, Oct. 24
Cast: Issa Rae, Yvonne Orji, Jay Ellis, Natasha Rothwell, Amanda Seales, Wade Allain-Marcus, Kendrick Sampson, Christina Elmore
Creators: Issa Rae, Larry Wilmore
As we watched Issa, Molly, Lawrence, Kelli and Tiffany break up, make up, get drunk, cry, kiss, the show slyly shifted its central question away from pure action (how to go after what you want) and moved toward meditation (wait, what do you actually want?). This reframing undoubtedly strengthened the series, allowing the writers to create more persuasive and affecting narrative arcs that deepened our understanding of the characters. That perspective, combined with Insecure’s lush visual language and apt musical choices, made the series a force — even when it faltered. Now, with its highly anticipated fifth and final season (of which critics received the first four episodes), the team behind Insecure, which includes Rae, showrunner Prentice Penny and director Melina Matsoukas, affirms the series’ legacy as an elegant and confident depiction of a specific kind of Black millennial experience.
In “Reunited, Okay?!,” the first episode of the new season, Issa returns to her alma mater for a discomforting 10-year reunion. It’s been a few weeks — maybe months — since Issa and Molly cautiously reunited at Merkato Ethiopian, the pair’s favorite restaurant, at the end of season four. When they see each other at Stanford, wearing matching crewnecks no less, their interactions are stilted, clearly bearing the weight of the hurtful truths they exchanged. Bringing the duo — whose friendship is at the heart of the series — to the place they met is a clever way to kickstart their reconciliation process. Still, this turn of events feels a bit too easy for a show that revels in wrestling with the messiest parts of close relationships.
Molly and Issa are in two different places when they see each other again. Molly has renewed commitments to work on herself, and her goal for the weekend is to stay present. There’s a refreshing shift in her character, who, since her heated and revelatory argument with Andrew (Alexander Hodge), possesses more self-awareness about her controlling tendencies. Issa’s back on campus not just as a nostalgia-seeking graduate, but as a participant in a panel of alumni entrepreneurs.
This all-expense-paid invitation affirms her professional ascent, although Issa herself remains unsure of her path. During the secondhand-embarrassment-inducing panel discussion, before a very different audience from the one she faced in the show’s very first episode, she answers a question that echoes those of the middle school students. “I don’t know if I’m on the right path,” Issa responds with her signature candidness. “To be honest, there is no way to be sure you’ve made the right choice.” She is no less lost than she was when we first met her, but there’s a resoluteness in her response that hints at a burgeoning confidence.
As with earlier episodes, Insecure opens its final season by deftly balancing its heavier themes with lighter moments. 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.
In a particularly exciting turn, the best part of this episode is its intentional focus on developing characters other than Molly and Issa. Rothwell’s Kelli, who has reliably provided some of the series’ funniest moments, assumes a more pensive disposition when she realizes that for some bizarre — and never explained — reason, the alumni committee thinks she’s dead and has planned an In Memoria tribute to her. It’s a dark turn that prompts Kelli to contemplate her legacy. How will she be remembered? What does she mean to her friends? At one point, she dejectedly wonders aloud if she’s only good for jokes.
Rothwell, who never misses a beat, assuredly transitions between Kelli’s caustic humor and a softer, more melancholic persona. That brief deviation from the usual enriches her character, and it makes me wonder if ending Molly and Issa’s story has to mean saying goodbye to Kelli. Maybe it’s about time she got her own spinoff.
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