Title: Cassandra’s Dream
Year: 2007
Genre: Crime, Drama, Romance
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Director:  Woody Allen
Screenwriters:  Woody Allen
Starring: Colin Farrell, Ewan McGregor, Hayley Atwell

Woody Allen’s Cassandra’s Dream is in many ways a retread of his acclaimed Match Point, exploring the same themes of luck and class mobility in the same morose slow-burn thriller format. The similarities are striking enough to obscure a crucial difference: where Match Point observed its scheming, largely amoral characters with cold cynicism, the new film has a deep, generous sympathy for the poor saps who populate it. Allen understands their longing and ambition, and his perspective doesn’t shift even as he leads them down a dark path.

It takes a while to realize this, because Allen’s tone — deliberate, portentous, with a clean visual elegance better suited for Match Point‘s country clubs than the blue collar haunts on display here — puts you on edge and makes you suspicious. I had trouble believing that Ian and Terry Blaine (Ewan McGregor and Colin Farrell), one a desperate, broke speculator and the other a compulsive gambler, are really just straightforward guys without much up their sleeves. I kept expecting a dramatic revelation about their pasts or motivations that never came, and it soon became apparent that Allen wasn’t all that interested in clever plotting or big surprises. So the biggest difference between Cassandra’s Dream and Match Point is this: the suspense in this film comes from inevitability rather than uncertainty. And that allows Allen to be kinder to his characters.

None of which is to say that he admires Terry and Ian, or that he wants us to do so. This is, after all, a story about two guys who agree to kill for their uncle. But in exploring what leads to the decisions that they make, Allen weaves a rich web of instincts, desires and motivations. He is clearly obsessed with certain themes and ideas, but not until the disappointingly schematic conclusion does he over-intellectualize the proceedings. Before then, the film is an engaging, thoughtful character study, the plot’s thriller trappings lurking uneasily in the background.

As is his wont, Allen traffics in a lot of ironies, a central one being the role that family plays in the Blaines’ decline. Every indication is that Ian’s family is holding him back — “it’s a mystery to me why he’s not more successful,” says his mother, but at least part of the reason is surely her husband’s reluctance to release Ian from his duties managing the family’s fledgling restaurant. What keeps him around seems to be some combination of loyalty and opportunism — he’s been taught all his life that family is family, and you take care of your own; at the same time, despite his grand plans to invest in a pair of can’t-lose California resort hotels, it’s hard to imagine him elsewhere, unable to borrow money from Terry’s intermittent gambling winnings, or cars from the shop where Terry works as a mechanic. When their rich, successful, generous uncle (Tom Wilkinson) comes asking for a favor — could they please kill the guy who is threatening to put him in jail — Ian sees the opportunity to strike a blow for himself but rationalize it as family loyalty. It’s underhanded and dishonest, over and above the fact that it involves murder, but Allen understands Ian’s desperation, and allows us to feel it. To some extent he’s an antihero, but he’s so sympathetic that he toes the line.

The last half of Cassandra’s Dream mostly deals with Terry’s crippling guilt, and Ian’s attempts to mollify him. Here Allen’s intellectual pursuits get the better of his filmmaking, as the two brothers unconvincingly splinter into moral mirror images of each other, Terry raving about “God’s law” and Ian losing even the most basic sense of right and wrong. The ending tries to ape Greek tragedy, but ends up contrived and false, as well as precisely the sort of haughty condemnation that is thankfully missing from the rest of the film.

The tone is tailor-made for the movie’s thriller elements, which work beautifully. There are some terrific moments of straight-up, classical suspense near the end of the second act, with Allen exhibiting the sort of patience and confidence that has often been missing from his neurotic, anything-for-a-laugh late-career comedies. And if Cassandra’s Dream doesn’t have the heft of Match Point, mostly thanks to an ending that tries too hard, I’d argue that it’s a much more human film. It wants to explore the darker dimensions of human nature, but it also wants to understand what cultivates them.

Seeking in movies meaning and reflection in real-time. On the look out for biography, thriller & drama best pieces.

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