As Cassandra’s Dream begins, brothers Ian (Ewan McGregor) and Terry (Colin Farrell) are already going through the predictable motions of one of Woody Allen’s class-mongering morality plays. These tallywackers buy a boat—they call it Cassandra’s Dream, after the dog Terry bet on and permitted its purchase, though The Aquatic Albatross or The Death Knell would have been equally fitting monikers—and soon they’re sailing the high seas, where their idle chatter is all about how they know what happened to “them” (Bonnie and Clyde), the beautiful day that’s “just right” (but soon won’t be), and how they’re dreams do not accommodate their father’s lowly restaurant. It is, quite possibly, the most strenuously overwritten scene of the filmmaker’s career.
If the condescending Allen doesn’t offer a context for Ian and Terry’s behavior it’s because he feels covetousness is a given for the lower class, and so Cassandra’s Dream is simply content reprimanding the brothers for not knowing their place. Allen first throws a wrench in their plans in the form of Angela (Hayley Atwell), a pretty actress and model Ian saves by the side of the road and subsequently woos because she’s not like any of the girls he typically dates—a point Ian makes within convenient earshot of the waitress he’s presently shagging. Angela is one of Allen’s familiar narrative conceits, a misogynist’s idea of a modern, liberated woman, prone to pathetic self-analysis like “I’m moody and self-obsessed,” though she mostly exists to advance the director’s lame—at once obvious and gratuitous—pretense to Greek tragedy (add lazy references to Medea, Clytemnestra, stir, then puke).
Regarding the part she’s currently playing at some off-West End venue, Angela notes, “The whole point of my character is to create erotic tension.” Then comes Howard (Tom Wilkinson), Ian and Terry’s uncle, who may as well have introduced himself as “Turning Point.” He offers the young men riches if they commit murder, assuring them, “You don’t build what I’ve built by playing by the books.” Weak that they are, the brothers don’t play by the rules of civilized society, and soon they’re caving in to weakness: Ian to the possessiveness that apparently comes with sudden wealth, and Terry to that odd feeling known as remorse. Would that Allen stopped playing by his own presumptuous and unimaginative training book: Another retread for the filmmaker, Cassandra’s Dream may as well have been called Match, Point, Set, only this one has Allen evincing an even shoddier backhand.