72 Hours is Kevin Hart’s midlife crisis comedy. He stars as Joe, a 40-year-old New York marketing executive whose once-reliable Midas touch has worn off. He’s no longer the office’s go-to translator of youth culture, yet he remains on the verge of a promotion – the final hurdle standing between him and happily-ever-after with his longtime girlfriend (Teyana Taylor), a doctor weighing an opportunity that could pull her away from the life they’ve built together in the city.

All the while, crude texts and memes flood his phone from a random group chat populated by a pack of twentysomething guys planning a bachelor party in Miami – an annoyance that quickly becomes his ticket back to relevance. Joe not only drops everything to join these perfect strangers for the weekend; he upgrades the whole affair, picks up the tab and supplies the booze in hopes of harvesting content for his struggling campaign. It would be a fine set-up if it weren’t such an obvious metaphor for Hart’s own showbiz career.

There was a time, in the not-too-distant past, when the kids were crazy for the 47-year-old Hart. Dave Chappelle had a whole bit in one of his standup specials about taking his son to see Hart perform live and the professional jealousy he felt watching the boy fan out over the guy, as if his own father wasn’t also one of the biggest names in comedy. The running joke with Hart was that he looked kid-sized next to other celebrities, a physical mismatch that fueled a towering Napoleon complex.

He invited audiences to laugh at his shortcomings as he ascended from the comedy club circuit to bit parts in movies like The 40-Year-Old Virgin and Little Fockers before becoming a leading man in his own right and starring opposite Will Ferrell and The Rock. What’s more, Hart was an underdog story: a scrappy Philadelphia kid whose first shot at movie stardom came as the lead in Soul Plane, a mega-flop he hustled to outgrow.

Just when Hart seemed too big to fail – no longer just a go-to headliner but the king of all media – the headwinds blew in again. He was involved in two headline-grabbing traffic incidents, one of which resulted in his arrest on drunk-driving charges, caught cheating on his pregnant wife and lost a dream job hosting the Oscars after old tweets in which he made homophobic comments resurfaced. But the bigger threat to Brand Hart has been overexposure. Him selling you a movie, then selling you the credit card to buy a ticket to that show or, perhaps, seats to his next cash-grab at the state-sponsored comedy festival in Riyadh. The idea that there doesn’t seem to be anything Hart won’t sell was reinforced by a recent Netflix roast that saw him laugh along as Shane Gillis, Tony Hinchcliffe and other white comedians delivered racially charged jokes not just about him but about George Floyd – a man whose memorial service Hart memorably attended.

72 Hours, which marks the eighth collaboration between Hart and the Ride Along director Tim Story, was supposed to be the comedian’s chance to turn the page from that controversy, as well as the legal battles raging within his embattled media company. Instead, the 105-minute picture offers the starkest proof yet of just how far Hart has fallen out of step with the times – the polished version of the unfiltered gen Z collaborations he has manufactured with Druski and Kai Cenat.

In place of those wildly popular internet personalities, Hart has ensconced himself among Hollywood’s freshest faces: SNL it-kids Marcello Hernández (as alpha-bro Nick), Ben Marshall (as lovesick Hunter) and Kam Patterson (as the lovable himbo Freshman), along with Mason Gooding – son of Oscar winner Cuba Gooding Jr and the young bachelor in question. And the chemistry within the group-chat clique is genuinely compelling. The guys might have an affection for crude memes and coarse language, but they also check in with one another emotionally before they party and preserve their shared memories in a physical scrapbook – a level of sincerity that doesn’t compute with Joe’s understanding of this supposedly terminally online generation.

A story about the four of them tangling with the bachelorette party quartette that drugs them and robs them blind would have been a much richer avenue for 72 Hours’ Cobra Kai-heavy writing team to explore. Instead, Hart turns the film into a platform for his longstanding grievances against cancel culture and political correctness while slipping into hackneyed versions of Puerto Rican and Chinese stereotypes. The R-rated script only makes matters worse by writing Joe, a 40-year-old, like someone twice his age – the kind of guy who downs two bottles of Pepto before a night of binge drinking and uses the latest wearable tech to surreptitiously capture footage of his new friends for his marketing campaign.

The meta-joke about an actor trapped inside his own midlife-crisis character doesn’t merely fall flat; it underscores the movie’s fatal flaw: 72 Hours would have far more potential if Hart weren’t in it at all. The insecurities that once made him relatable aren’t comic any more. They’re sad.

• 72 Hours is now available on Netflix on 24 July