In its fourth season, premiering Sunday, "what’s changed about Insecure isn’t Insecure itself. It’s what we’re bringing into it," says Alison Herman. She points out that what Issa Rae's HBO comedy does best is show beautiful, charismatic people enjoying one another’s company -- something that's forbidden in the current coronavirus crisis. "Insecure has long styled itself as a paean to 2010s L.A., much in the same way that Sex and the City was an ode to early-aughts New York," says Herman. "(Though with its emphasis on platonic coupledom, a closer comp might be Broad City.) Issa lives in Inglewood, a historically black city next door to the airport, but Insecure films all over, from iconic Hollywood locations like Swingers—site of the infamous fingering scene in Season 2 (which shut down permanently this week after 27 years)—to trendier areas like the Arts District. Issa and her friends, many of them Southland natives, don’t have to choose between their identities as black Angelenos and clout-chasing millennials. They, and Insecure, can cover both terrains. The latest volume doubles down on this theme with its most prominent subplot: Issa, now working part time as a property manager and without a salaried job, is trying to organize a massive neighborhood block party highlighting local artists and businesses, a monthslong process that takes up the bulk of the season....It’s now common to observe the disorienting, uncomfortable feeling of watching television characters congregate in public when so many of us are sequestered in our homes. Still, there’s a particular pang of nostalgia to watching fictional people visit the real places you would visit and do the real activities you would do, if you could. Artfully staged and aspirational, Insecure is meant to be an escape. This time, it’s a far more literal one than its creators could’ve intended."
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Insecure Season 4 is like strapping yourself into a time machine and traveling to an alternate universe: "It’s a world where people in Los Angeles still go to busy coffee shops and bowling alleys, instigate late-night booty calls, and hike on Sundays with people they don’t live with," says Tomi Obaro. "That the new season is centered around Issa’s attempts to mount a block party in Inglewood certainly doesn’t help with the surreality of watching the show now. Remember block parties? Where strangers inevitably rub up against each other, jostling to see the headliner, eating street food with their germ-infested, unwashed hands? Insecure is not the only TV show where this disconnect will occur, of course; new and forthcoming seasons of many series that are supposed to be set in contemporary times will automatically seem antiquated by default when they eventually air. The new fourth season of High Maintenance, whose finale aired on HBO last Friday, is also wild to watch now — hinging as it does on chance encounters between New Yorkers and a weed dealer who isn't afraid to visit people's apartments without personal protective equipment. Both shows adhere to a certain kind of verisimilitude. They’re both comedies anchored by the details of daily life in bustling big cities that allude to current events, be they politics or economic struggles, in a way that makes watching them now, as we live through an unprecedented time, feel particularly strange. They are stark reminders of the world we used to live in — a world that doesn’t exist anymore."
Insecure is stuck in a rut in Season 4 with too much focus on guys: "I’ve seen the first five episodes of season four, and the show, instead of broadening its scope or deepening its exploration of existing relationships, has become repetitive, relitigating the same triangulated conflicts between Issa, Molly and whichever man happens to be in the third corner," says Soraya Nadia McDonald. McDonald adds: "There are plenty of possibilities to mine with two women struggling to maintain a longtime best friendship, especially as Issa and Molly drift apart and each phone call or text becomes more awkward and labored. There’s simply not enough in the show to bolster it. Without the assortment of socially maladroit weirdos who populated Issa’s former job at We Got Y’all, Rae and Orji are left to do more of the heavy lifting. Paradoxically, what they’re lifting is largely skeletal. Scenarios such as Molly’s running feud with an associate at her law firm, or the gentrification occurring in Inglewood that spurred Issa to organize the block party in the first place, both need further development. Season four feels as though it came out of a writers room struggling to push beyond what the show established in the three previous seasons. Someone also needs to be brave enough to ax Lawrence for good. As a character, he’s just not interesting enough to merit the continual will-they-or-won’t-they merry-go-round he and Issa keep riding."
Insecure is as funny as ever in Season 4, but it doesn't have the lighter spirit of past seasons: "Issa Rae's tart HBO comedy returns with a rapid-fire joke rate, despite an unexpectedly downcast mood," says Robyn Bahr. She says of Molly and Issa: "Each woman came to a personal reckoning in the series' third outing, which aired during the summer of 2018. Flailing Issa found — and lost — a new love interest, but obtained some measure of closure with her ex, Lawrence (Jay Ellis). Even more important, she gained new footing in her career and financial security, first by become a building superintendent, for reduced rent, in a new apartment complex, and then by quitting her job at a nonprofit to pursue community event planning. Meanwhile, perfectionist Molly finally allowed herself to open up to a man who didn't meet her exacting (and unrealistic) criteria for romantic partnership. But given these forward strides, why does Insecure — otherwise still home to some of TV's funniest one-liners — feel like it's just ending up in proverbial 'old sh*'?"
Insecure remains, hands down, the best-shot series set in Los Angeles currently on television, and it treats the city with respect and appreciation: "Where Netflix’s winter hit second season of You offered a shallow parody of L.A.’s yoga-doing, oat milk-slurping population, inducing eye-rolls for anyone who actually lives there, Insecure has empathy for the city of dreamers and hustlers," says Ryan Lattanzio. "It’s a treat to play 'I spy' with the various landmarks and neighborhoods that are rendered vividly alive, and Rae continues to use the landscape as a sandbox in which to explore hard truths with often wincing hilarity."
Insecure's Alexander Hodge on playing "Asian Bae": “What I love, and we're seeing more and more of it now, is I love seeing the character breakdown for an Asian guy who is confident, who is grounded, who goes after what he wants," he says. "I loved that the character breakdown didn't mention his job, it didn't mention what he did for a living. Automatically, it wasn't about filling a stereotype, it wasn't about playing a tech worker, it wasn't about playing an accountant, or anything like that. It was actually about the essence of this guy."
Issa Rae is tired of people complaining about her juggling Insecure with many other projects: “People think that you’re just sitting on it and being petty,” Rae says. “When they don’t see you, they just really think you’re not working. So I was grateful to the people who are just innocently missing it. And f*ck you to the people who, when I would post a picture of my mom, would be like, ‘Where’s Insecure though?!'"