Synecdoche, New York

A middle-aged man in crisis finds himself contemplating his mortality, loneliness and insignificance in a vast, indifferent universe.

These are the sort of grand existential themes that are normally associated with filmmakers from a more literate age, such as Luchino Visconti or Ingmar Bergman - but given that Synecdoche, New York is the directorial debut of one Charlie Kaufman, who has previously penned such high-concept experiments as Being John Malkovich (1999), Adaptation (2002), Confessions Of A Dangerous Mind (2002) and Eternal Sunshine Of The Spotless Mind (2004), you can be sure that this most straightforward and essential of premises is going to be elaborated, ramified and fragmented into something far more brain-bending, if no less poignant, than anything made by his predecessors.

The protagonist Caden Cotard, himself a director, albeit of theatre, may well wonder aloud near the film's beginning why he, like Kaufman, always makes his productions so "over-complicated", but the answer is more or less the same for both artists: they are re-staging classic tales of the human condition for a decidedly postmodern mindset.

In Schenectady, New York, it is October – "a melancholy month, and because of that quite beautiful" as a poet is heard saying on the radio, perfectly summarising the mood of the film to follow. If it is the beginning of fall, then these are also the autumn years of Caden Cotard (Phillip Seymour Hoffman), who finds himself left alone at home with a series of physical and neurological ailments while his wife Adele Lack (Catherine Keener), a painter of miniature portraits, is off touring Berlin with their four-year-old daughter Olive (Sadie Goldstein).

Too miserable, sick and guilt-ridden even to consummate his affair with Hazel (Samantha Morton), the adoring box office employee at the theatre where his latest production, a modernised Death Of A Salesman, has just opened, Caden feels abandoned, lost and impotent – but then an unexpected grant arrives, offering the director an opportunity, for the first time in his career, to develop his own ideas. Moving his entire company to a giant warehouse space in New York City, Caden decides to go with what he knows, and so embarks on an ambitious project to turn his own life, and all his anxieties about loss and death, into one vast all-encompassing play.

Caden neurotically dramatises his estrangement from his own daughter, 'now' a grown-up tattooed lesbian who speaks only German, and imagines a second (failed) marriage, this time with his lead actress Claire Keen (Michelle Williams), while he continues to obsessively pursue his elusive first wife Adele, the now married Hazel and even his own (or at least someone else's) mother. Soon the sheer scale of the project, stretching decades into the future, requires Caden to hire doubles (and eventually triples) to portray both himself and the other people in his life – not to mention an ever-expanding army of extras.

When Caden's double (and one-time stalker) Sammy (Tom Noonan) begins going out with Hazel (who is now working as Caden's assistant), Caden finds himself settling for Hazel's double Tammy (Emily Watson) as "the next best thing". This is, after all, 'the story of Caden's life' in more ways than one – a story of regretful substitutions and disappointed projections. In the end he will allow Millicent (Dianne Wiest), a woman originally hired to play Adele's (entirely imagined) cleaning woman, to take on the role of Caden himself, and then cede even his directing duties to her, as he comes to realise that his own flawed existence is shared by a whole universe of human extras - in a meaningless theatre of the absurd, directed by a complete stranger, where the only thing predictable is the end.

Synecdoche, New York is a film like no other, coming from a filmmaker who is beginning to specialise in the 'film like no other'. It is not an easy brand to maintain without succumbing to the self-defeat of repetition – and yet Kaufman somehow manages to avoid rehashing his old ideas, even though this film is itself concerned precisely with repetitions, parallels and symmetries. Its closest analogues are not in cinema, but rather in the plays of Luigi Pirandello or Samuel Beckett (or even the more meta-theatrical moments of William Shakespeare), but perhaps that should not be surprising given that this is a film about a play - a play that could not possibly be staged, that is as maddeningly messy as life itself, and that might just be the hallucinated product of Caden's 'synaptic degradation', of a bad trip, or even of just a particularly vivid fever dream. Are we watching a man's life flashing before his eyes in the moment that precedes death, or several decades of continued decline - or is it just two hours of wondrously compressed and convoluted cinema, encapsulating the simplicities and complexities, the specificities and the universality, of any individual's all-too-brief existence?

In any case, it is dizzyingly rich in ideas, it is remarkably free of exposition - or, indeed, of any kind of concession to those who are not up to its sophisticated mode of reflexive game-playing – and it is unapologetically a film for adults. What really makes it stand out, though, even from the rest of Kaufman's own oeuvre, is its tone of sombre resignation.

Synecdoche, New York may feature all the filmmaker's usual surreal wit and close observation of human foibles, but at heart it is a memento mori of unfathomable gravity, and few will still be laughing by the final scene. For both Kaufman's film and Caden's play are a metaphor for not only the miraculous creativity, but also the bleak futility of all human endeavour – and in this portrait of an artist as an old man in decline, no amount of reproduction, trickery or fantasy can or ever will suffice to deflect the inevitable end (even if no one could quite anticipate the particular theatricalised form that the end will take here).

Phillip Seymour Hoffmann is riveting as Caden, bringing to the surface all this narcissistic hypochondriac's doubts, confusion, yearning and despair – and the ensemble in his orbit proves as committed and capable as Caden's own theatre company. Kaufman can certainly direct, too, seamlessly enmeshing reality, fantasy and performance so that the viewer easily becomes as lost as Caden himself. With the clock ticking on Kaufman as much as on the rest of us, it is impossible to know what he might do next, but to date this is without question his finest and most important work, and one that already has the feel of a classic (or at least an epitaph) about it.

At one point near the end, our disgruntled protagonist is heard declaring to Hazel, "God, you're perfect", to which she replies, "I'm a mess, but we fit." It is the film – and perhaps life - in a nutshell (or, if you like, in synecdoche): a collection of loosely linked episodes of human fallibility that somehow adds up to divine perfection. See it and weep – even if you have to use actor's eye drops to s(t)imulate the tears.