Woody Allen's London trilogy closes with a whimper in "Cassandra's Dream". In a culmination of Allen's sustained misanthropy, this trilogy (along with "Match Point", "Scoop") continues to canvas the moral complexities inherent in his entire oeuvre, where the petty motivations of a misdeed and its postmortem of soulless brooding are wanly gazed at by an omnipresent moralist, the mode Allen once again condescendingly occupies with no real concern for either victims nor criminals or for that matter, anyone else caught in the middle.
It is a curiously self-contained endeavour. With "Match Point", he returned to the scene of his "Crimes and Misdemeanors", exploring with a freshly glazed eye its characters' tumble into a moral morass tipsy with self-loathing bourgeois officiousness. In "Cassandra's Dream", Allen merely repurposes "Match Point" to bookend his sojourn into London's social classes (from his first film's look at the upper-class to the middle-class in "Scoop" and here, its working-class) as he looks with one eye towards the greener pastures of Barcelona.
Disengaged, lifeless and drenched with a moody cynicism, Allen finds no comfort in the world of desperate men. Underachieving brothers Terry (Colin Farrell) and Ian (Ewan McGregor) live large while bills and debts go unpaid. Terry's a feckless gambler who looks for small payday, while Ian, with a more precise and ruthless ambition, looks for his financial escape through high-risk, high-return ventures in speculative property deals as he works his way out of his father's modest restaurant. Uncle Howard (Tom Wilkinson) is their ideal. A self-made millionaire, with a house in California and opportunities in China, Howard's bailed his family out of financial ruin a few times. His ominous return to London coincides with the brothers' sudden and frantic need for money. The dangerously fuelled idea of family is invoked many times in Allen's story; from the moment Howard proposes a blood-laced quid pro quo to the point when a final meal is acquiesced with a loved one.
Allen falls back on broadly drawn characters, stilted theatrics, painfully obvious exposition and overwritten insights on the human condition when faced with remorse, torment and the roots of evil. The film is by no means witless but merely passionless in its connotations to pretentious Greek tragedies. The key premise falls short when it stumbles the second the deed is done when Ian coasts through the waves of guilt of which Terry bears its full brunt just as he wises up to his brother's nihilism.
Keenly self-referential, Allen knows the place of each and every character and what they represent in the film's final tableau but just lacks the panache to present them as more than just pieces to a puzzle. The title itself signifies a Greek tragedy in the offing but only hints at the idea of truth being spoken and unfortunately heard, whereas Cassandra in the original Greek myth portents the truth and was never believed.