How do you update Shaft for the modern era? John Singleton tried in 2000 with a serviceable if unspectacular sequel, a rather asexual and anonymous follow-up to the far more stylish and distinctive original. Almost two decades later and somehow we’re even further from the right answer. Because it turns out that a 2019 version of Shaft probably shouldn’t turn into an unabashed celebration of regressively misogynistic and homophobic masculinity. In Ride Along director Tim Story’s wildly misjudged follow-up, we’re given a Jordan Peterson-level assault on so-called beta millennial males, a strange, angry attack on modernity that feels like the result of a group of bitter men griping about the metrosexualisation of a younger generation.

In the latest incarnation, the younger Shaft, played by the undeniably charming Jessie T Usher, is a decaf coffee-drinking, gun-hating, women-respecting data analyst for the FBI, which turns him into a joke and a punchline for both the film and his absentee father. Played by a returning Samuel L Jackson, he’s disgusted to see what his son has turned into at the hands of his mother (a wasted Regina Hall), who raised him in his absence. Convinced he must be gay, he’s determined to turn him into his idea of a real man as the pair investigate the death of younger Shaft’s ex-junkie friend. There’s an inevitable culture clash between the two but elder Shaft is focused on showing his son that listening less to women and shooting more guns will help to show him the way.

There’s a smart, self-aware film to be made from a rough kernel of this setup. Focusing on the different definitions of masculinity shared by two generations of men is an intriguing entry point, especially given that one is a father who hasn’t been present for his son’s youth. There’s space for suggesting a happy medium between two extremities but Story’s update has zero interest in nuance or even debate. We’re shown time and time again that for the younger Shaft, the more he embraces modern, “softer” qualities, the less of a man he then is. Skinny jeans, coconut water, desk work – all treated with unbridled disdain as for his father they all symbolise femininity or, even worse, homosexuality. The film is littered with uneasy jabs not just towards gay men but also the trans community (young Shaft’s boss complains that his biggest problem is that his daughter “wants to be known as Frank”). “You sure you like pussy?” is repeated by a concerned Jackson with such alarming frequency that I was tempted to ask the critic next to me whether we had somehow been magically transported back to the 70s.

But even in the 1971 original, sexual and gender politics were far less troubling. Back then, Shaft even had a gay friend of sorts, a barman who he treated as his equal, but somehow almost 20 years later, every reference to homosexuality is dripping in bile. While 70s Shaft might have been dismissive about the women he was having sex with, he didn’t feel the need to pause the film to give a sermon about how all women desperately want and need to be treated with unquestioned strength and power, something that the modern incarnation deems necessary. It would be one thing if the film presented him as a dinosaur but the script, from Black-ish creator and Girls Trip co-writer Kenya Barris and Family Guy’s Alex Barnow, is too busy hero-worshipping him to bother finding fault.

The film presents us with two outwardly strong female characters, in Hall and younger Shaft’s love interest, played by Love, Simon’s Alexandra Shipp, but any feistiness is soon overruled by their visible arousal at men being men. In one of the film’s strangest scenes, younger gun-hating Shaft is forced into a shootout as his date watches smiling, turned on by his blood thirst. Similarly Hall’s date with a beta male (who’s treated with contempt for having manners and being scared by another shootout) is interrupted by a swaggering Jackson, the man who abandoned her with a baby, making her quiver by showing off the two women he has arrived with and embarrassing her date.

Alexandra Shipp, Jessie T Usher, Samuel L Jackson and Richard Roundtree in Shaft. Photograph: Kyle Kaplan/Warner Bros

Even outside of the script’s aggressively repetitive bigotry, the shambolic Scooby Doo plot struggles to grab even the slightest amount of attention. There are half-assed attempts to modernise a familiar narrative with references to an Islamic church and men suffering from PTSD but it soon devolves into dull, by-the-numbers, jarringly over-sentimental sitcom. When action arrives it’s also haphazardly choreographed, especially in a shoddy, confusingly shot finale. Jackson shamelessly showboats throughout but his charisma is buried underneath a shtick that becomes so gratingly obnoxious I almost applauded when Richard Roundtree’s original Shaft made his inevitable cameo. But rather than saving the day, he’s given little to do, and the script chooses to defend both admittedly terrible absentee fathers while throwing Hall’s beleaguered single mother under the bus for feminising her son. It’s frustrating to see such an underrated comic actor like Hall struggle to find space to shine, although she does provide one of the film’s rare funny moments as she talks to herself in a public bathroom. Usher similarly, who was so good in the now cancelled TV comedy Survivor’s Remorse, does his best with a crudely etched character, but any resistance against the film’s regressive politics is ultimately futile.

The mission in Shaft is to break down a modern definition of masculinity, to toughen up “delicate” qualities, such as hating guns and listening to women, and return to the good old days instead. While Jackson’s ribald relic might succeed in forcing his son back to the past, this embarrassingly tone-deaf film fails to take us with him.