In Cassandra's Dream (2007), Ian (Ewan McGregor) and Terry (Colin Farrell) are brothers living in London, two shades of loser both hard up for cash. Ian works a dead-end position at their father’s restaurant, but dreams of living an upper-class life complete with a beautiful wife, elegant yacht, and a vacation home in California. Terry is very content with his life as an auto mechanic but has a crippling thirst for gambling. Both men are perpetually short on the cash needed to get by day-to-day, let alone indulge in their daydream-vices that keep them perpetually stressed and striving. 

Ian has bluffed his way into a relationship with Angela (Hayley Atwell), a beautiful actress who is self-admittedly preoccupied with material gain and wealth, with a convincing line about pending real estate investments and hotel interests. He knows he has to deliver on some of his promises or else Angela will set her sights on a more eligible man. Terry is in hock to a loan shark for £90,000 after a bad run of gambling. Both men are becoming desperate.

The brothers’ vices: (left) For Ian (McGregor), a life he can’t afford; for Terry (Farrell), the rush of gambling

Enter Uncle Howard (Tom Wilkinson), their mother’s elegant brother who seems to have the Midas touch. Uncle Howard travels the world on vague business ventures and appears to be living the high life that Ian so desperately craves. The boys go to their uncle seeking “loans” they have little hope of paying back, and Howard is agreeable to the boys’ request. But he has one of his own.

Howard needs someone killed. There’s a business rival who knows too much about the shady elements of Howard’s business, and if this man talks Howard could go to jail for a very long time. Now he’s just found two young men who owe him a big favor. In just a few moments, the idealistic image that Ian and Terry have held of their shining uncle has vanished, replaced with one of a ruthless crook who is willing to take advantage of anything and anyone.

Debating Uncle Howard’s proposition

This dilemma that the boys find themselves in is the centerpiece of Cassandra’s Dream: How far are people willing to go to realize their ambitions, and is the price paid going to be worth it? Ian initially believes it is—a lifetime of financial security and romantic bliss in exchange for a few unsavory hours—but for Terry the prospect is much more horrifying. Ian begins to plan his new life in anticipation of his windfall, taking care of the logistics involved in planning a murder as if he were packing for a vacation. Terry begins to have nightmares about the impending hit and starts drinking heavily and becoming erratic. Ian’s concern about his brother is a self-centered mix of worry and annoyance—he needs his brother cool and reliable to ensure Howard’s plot goes off smoothly, and he also can’t have Terry blurting out their plans in a guilt-ridden blackout.

Weighing the proposition

What could be treated as a seedy little story about a few desperate nobodies becomes an elegant Faustian bargain in the hands of writer/director Woody Allen and actors McGregor, Farrell, and Wilkinson. McGregor is perfectly light as Ian, keeping his tone so bright when discussing murder that one isn’t sure that the film won’t veer back into more familiar Allen territory of misunderstandings and ill-placed love. Farrell’s Terry is a sincere, shaky bundle of worry, and Wilkinson’s unmatched ability at depicting magnetic, mercurial figures makes him thoroughly convincing as the charming and corrupt Howard.

Moral dilemmas often crop up in Allen’s films, but they usually involve infidelity and interpersonal relationships that can eventually be smoothed over to everyone’s benefit. The few times that transgressions of a criminal nature have been dealt with—most prominently in Crimes & Misdemeanors (1989) and Match Point (2005)—Allen holds steadfast to the argument that morality is in the eye of the beholder. If you feel guilty, the guilt will catch up with you and destroy you. If you absolve yourself for the evil acts you commit, no one has the right to punish you. By removing any objective or divine sense of retribution the director lays bare how amoral acts bring out the true nature of one’s character. His bleak attitude towards what humanity is capable of ensures that those who are less hampered by an inner sense of punishment will prosper and those who feel guilt will become weak and crippled. Police investigations are shown only as an afterthought, an extension of the protagonist’s personal sense of retribution. It’s this nihilistic view of justice that makes Cassandra’s Dream so gripping: we’re not worried that the police will get wind of the brothers’ plot, but we are worried about how harshly they are capable of punishing themselves.

Cassandra’s Dream is available to rent via streaming from Vudu and Apple, and on DVD from Netflix. To get new essays delivered subscribe here