Insecure Season 5 Review – Farewell to the most fun, excruciating comedy on TV

Posted On: October 27, 2021
Performers: Issa Rae • Category: Comedies, Comedy Series, Comedy Specials, News, News Features, Social Buzz, TV Shows, TV Specials

There’s a crisis brewing in the TV world: no one can nail an ending. Indeed, almost every recent hit show, from Vigil to Squid Game, has delivered a decidedly lacklustre conclusion. Even the finale of The White Lotus – delectably twisted in so many ways – left viewers divided.

Thankfully, it’s not a problem viewers are likely to have with Insecure (Sky Comedy), with Issa Rae recently promising not to pull a “Game of Thrones”. From the four episodes available for preview, the fifth and final season of her comedy about a group of black millennial girlfriends is all about giving its fans what they want. Namely, will-they-won’t-they drama, existential crises and pitch-perfect Kelli-isms. Rae’s star has risen in recent years – she’s gone from merely being a New York Times bestseller and the maker of a cult webseries to a bona fide media mogul, reportedly landing a $40m deal with HBO – and it shows in season five’s greatest-hits feel.

The first instalment finds Rae’s character, Issa Dee, back at Stanford for an alumni weekend. The smallest signs – an eye-roll from Issa, an overly long complaint from Molly (a perfectly restless Yvonne Orji) – hint at still-unresolved issues between the pair, who ended last season with a tentative truce. Once again, Insecure showcases how familiarity breeds contempt, and how just maybe – as Issa and Molly skip a trip to a dive bar in favour of sharing a bottle of wine – our oldest friendships might be reimagined and reconfigured.

Last time around, we saw Issa get a foothold in the business world, organising a block party to spotlight black-owned businesses in her increasingly gentrified corner of Los Angeles. However, season five doesn’t give her a #girlboss fantasy. Rather – despite the snazzy business cards and brand partnerships – we see Issa spiralling into self-doubt. In a brilliant, excruciating scene, she takes part in a panel for entrepreneurs at her alma mater. When did she know, she is asked, that she was on the right path? “The right path …” she stumbles. “I don’t know that I’m on the right path? To be honest, there’s no way to be sure that you’ve made the right choice. Maybe I’ll wake up tomorrow and realise that I’ve wasted all my time … and that’s time I can’t really get back.” Outside, Molly shoots her friend a “wait, what?” look, as Issa puts on a slightly manic display of being completely fine.

The idea of being on the right path, or otherwise, has dominated Insecure since the start, via Issa’s on-off relationship with Lawrence (Jay Ellis) and Molly’s self-sabotage-fuelled revolving door of boyfriends. Season five only underscores the theme. As it continues, we see how Lawrence is coping with fatherhood after his shock pregnancy with Condola (Christina Elmore); how Issa’s professional insecurities intersect with her personal life; how Molly’s personal life clashes with parental expectations (namely that she should date an acquaintance from church, whose gambit is “I rework trap songs for the lord”); and whether these bright young things really can have it all.

Like the best sadcoms, it does all of this with a lightness of touch, retaining the quirks that got Rae noticed with her Awkward Black Girl webseries. Her comic DNA remains unaltered, as evidenced in the magical realism moment when Issa – first seen in Insecure rapping to herself in a bathroom mirror – finds herself in the WC once again, offering advice to a younger self who seems unimpressed with how her life has turned out. “Photos on an app, invent that shit. Call it Issa-gram!” she orders. “What’s an app?” asks the kid in the mirror.

For all its angst, Insecure remains resolutely fun, with Natasha Rothwell’s Kelli still delivering the best zingers. It’s hard to believe we last saw her as the put-upon massage therapist Belinda in the aforementioned White Lotus as she describes babies as demons. An administrative error sees her accidentally added to an in memoriam presentation at the college reunion, leading her to declare that she “came back like Daft Punk: better, faster, stronger!”

Unlike so many other shows, Insecure seems determined to go out on a high, its final episodes more of a parting gift to fans than a collection of mic drop moments. It remains to be seen whether this Issa is on the right path, but it’s clear that Issa Rae is.

As seen on: Insecure season five review – farewell to the most fun, excruciating comedy on TV | Television | The Guardian

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