Towards the end of this ill-conceived remake, there is a scene that briefly hints at what might have been. Alfie, like a petulant child, asks middle-aged Liz what her new paramour has that he hasn’t. Liz hesitates, smiles, and says ‘He’s younger than you are’. Cue comeuppance for Alfie, empowerment for Liz and a wonderfully sustained quiet moment amidst two hours of misogynism and macho posturing.

Michael Caine was the original Alfie in 1966, but Law’s physical resemblance to him ends the comparison. While Caine was slick and deceitful, Law plays it safe, unwilling to alienate his fan base. As a chauffeur driver cruising the streets for one-night stands, his Alfie sips carrot juice and delivers straight-to-camera monologues like pantomime asides.

Transplanting the story to Manhattan seems nothing more than cynical button-pushing. Vertiginous overhead shots of the Chrysler Building and neon-lit jazz bars may appeal to visual cinephiles, but scarcely seems relevant. Swinging Sixties London was the site of the original, and Lewis Gilbert captured its seamier, less glamorous side. New York 2004 has been chosen, it seems, solely because of the plethora of pretty girls.

There’s no consistency in the screenplay, either. Acts one and two seems like two completely different films – the overly fastidious cinematography doesn’t help – while a brief sub-plot involving an out-of-town trip seems imported from an entirely different movie altogether. You know you’re in trouble when the screenwriter resorts to the hoary cliché of the older, wiser figure to help the plot move along. As for consistency of style, the film lurches awkwardly from laddish rom-com to moody chamber piece to slushy melodrama, while all the while slowly being strangled to death by the production design.

Director Shyer seems unable (or unwilling) to bring complexity and subtlety to proceedings. For such a time-specific film, the original had its insights, but by contrast, this version is infected with a bitter taste of chest-beating masculinity that precludes any real affection of the titular character. Law is suitable charming in a role that many may see as a variation of his real-life self, and there is no doubting his surface beauty. But he seems hamstrung in many of the film’s more tender moments, as if the emotional autism of his character has spilled over into his acting. It doesn’t help that he is suffocated by his costumes – yes, he looks good in Gucci and Prada – but the audience is restless for character motivation. There’s no political comment either – in 1966, the pill and abortion were highly topical issues; Law’s Alfie seems oblivious to AIDS or feminism.

Of his female conquests, the acting is suitably one-dimensional and Krakowski, Tomei and Miller are all elegant. ‘Loaded’ readers may whoop with joy as Law’s explains the intricacies of break-ups and the joys of singledom, but one wishes Shyer had the wherewithal to make these ramblings an ironic comment on the emotional vacuity of such behaviour. What can only wonder what, say, Dylan Kidd (whose Roger Dodger (2002) was a more polished version of the same themes) would have made of it.

Far better, as Kubrick did in Eyes Wide Shot (1999) – another film about a pretty-boy looking for sex in the city – to make New York some kind of dream-space, inhabited by disconnected people in anonymous rooms. Instead, Alfie quickly loses any good will it had generated by introducing clunking devices like an irascible Chinese boss or a cross-eyed florist. Law may be the ‘degree-zero’ of beauty, but the mockery of others in the film is consistently disheartening.

The saving grace? Sarandon, looking every inch the stunning beauty she has aged into over the last decade. Her fragility is perfect and her rejection of Law’s puppy-love advances deeply heartbreaking. But not heartbreaking for him – we care little about Law, as his final monologue confirms – but for her. Liz is hopelessly lost in this city, desperate to find real happiness. Her’s is a story that we are impatient to follow, but, given the emphasis of Bill Naughton’s original screenplay and Shyer’s inept transposition, it remains lost amidst the smugness and the preening.