For nearly three decades from the 1970s onward, Woody Allen was the most New York of all New York directors. From Annie Hall to Manhattan Murder Mystery, the Big Apple was the muse of this Brooklyn-born auteur. But in his last three films—Match Point (2005), Scoop (2006), and now Cassandra's Dream—Allen has found a new urban inspiration: London.
He has also shifted themes toward more deadly serious drama, at least in the case of Match Point and Cassandra's Dream. Those of us who prefer this Crimes and Misdemeanors-type Allen are doubtless happy about this trend. Cassandra's Dream is certainly not a crowning career achievement for Allen, but it's a solid companion piece to Match Point.
One of many things Dream and Point have in common is a profound undercurrent of class-consciousness. Perhaps this explains Allen's turn toward Europe as a setting. America, after all, is among the least class-concerned countries in the West. In England, however, stratified wealth is a huge issue (see Altman's Gosford Park for a good example of this). Like Match Point, Cassandra's Dream explores the ambitions of young working class lads trying to infiltrate the aristocracy and move up in the world.
Dream begins with two working class brothers, Ian (Ewan McGregor) and Terry (Colin Farrell), purchasing a sailboat with money they don't yet have. Terry is a mechanic with a poisonous penchant for drinking and gambling (they name the boat "Cassandra's Dream" after a 60-1 winner at the dog races), though he has a soft heart and rather meek ambitions in life. Ian is the more high-minded of the pair—a Gatsby-esque playboy with a keen mind for the importance of appearances. He dates, deals, and associates with people well above him on the ladder of success, and is desperate for a chance to ditch the family restaurant business for bigger and better things ("I wasn't put on this earth to run a restaurant"). These boys are affable and normal enough—which makes their bourgeois struggles all the more resonant. Unlike Match Point, in which the protagonist was a rather unlikable miscreant, these guys are simply trying to do better by themselves. Unfortunately they make some poor decisions along the way.
By the end of the first act, both Ian and Terry are in dire need of a lot of quick cash (always a foreboding setup). Ian has a new actress girlfriend, Angela (Hayley Atwell), who thinks Ian is a successful hotel entrepreneur, owns a Jaguar convertible, and is a proven member of the leisure class (all false). So as not to lose her, Ian needs a lot of money to prove he belongs in the country club life. Meanwhile, Terry needs to pay off 90 grand in gambling debts, lest the loansharks "break his legs" or worse. Fortuitously—or fatefully—rich Uncle Howard (Tom Wilkinson) comes to London from abroad with deep pockets and a mercenary proposition for his nephews: I'll give you all the money you need, if only you do something rather substantial for me. That "something," of course, turns out to be a murder-for-hire.