It's a GREAT ending! It's similar to the ending of Melinda and Melinda; i.e., "Life can end, just like THAT! (Cut to black). This ending was foreshadowed by a poet's line "The only ship certain to come in has black sails"; i.e., death. "Cassandra's Dream" is a metaphor for high risk crash-and-burn behavior. As the final master shot focuses on the boat, itself, police inspectors, who can't understand the cause with absolute certainty but are witness to its effect, and are heard to say that "every day it's something else". W A is a creative film maker whose films occasionally have an experimental, groundbreaking quality. He also establishes characters with succinct exposition. This film isn't just an isolated story about specific personalities. What makes it very good if not absolutely great is the generalizations to be drawn from this instance that apply to the universe of humanity. Tragedy may follow if passion is not tempered by reason. People set traps for themselves and then fall into them. Part of the destructive impulse can be due to a codependent reaction of a younger vs. older generation. This is also escapist behavior which seeks to substitute fantasy for reality in order to break the material and spiritual bounds imposed by social class. Such risk-prone behavior is complicated and is easily and widely reproduceable.
As broader social commentary wealth, fame, and power are things that tend to corrupt. Both brothers seek wealth in order to exercise power in order to obtain sex and trophy girlfriends and thereby obtain, if not fame, then envy. The quality of their sex is "wonderfully depraved" or "innocent and also depraved". Two females, Angela the actress and an unnamed tall blonde friend of the uncle's business associate Martin, are willing to supply sexual favors in a calculated way in order to enrich their personal lifestyles and/or achieve comfort or fame. Ian humiliates his rather plainly made-up girlfriend Lucy the waitress after dumping her for more beautiful Angela the actress as he discusses his preference for the new girl in the presence of his father and the waitress. Woody's film makes a statement that this type of high-risk behavior is not the way to achieve either material success or to create abundance or happiness. In another film, mostly about fame, in which gambling and debt is also a factor, "Celebrity" begins and ends with the word "HELP!". "Cassandra's Dream" the boat itself, bookends this film, "Cassandra's Dream", which again is the metaphor for an unheeded warning and call for help that goes unrecognized until it is too late. The metaphorical ship with black sails was also used for a sequence in "Scoop". "Dream" contains a toxic mix of lust for sex, wealth, fame, and power that interferes with financial stability, piece of mind, and also true, uncorrupted love.
While the film shows what not to do, it doesn't show anything about the process by which wealth and power may be generated throughout one's working life in a manner consistent with ability to manage risk consistent with available equity. This is beyond the story's scope. The lower-class parents have been frustrated by their lack of greater success. Their lack of knowledge was a source of frustration for both brothers and the actress who have chosen to engage in high-risk behavior in rebellion to the deprivation of their respective households and manner of upbringing which has counseled against it. Kate, however, appears to be more moderate and reasonable. At least she disapproves of high-stakes gambling and expresses concern about spending. The story content involving one generation's rebellion against its lower-class parental conservatism and restraint may very well be autobiographical.
"Cassandra's Dream" is a bold, confident, simple story. Its biggest plot twist occurs when the brothers suddenly discover that their uncle is just like them. All have "crossed the line", and must confront unforeseen, unintended, tragic consequences that are to become their fate. The brothers, uncle, and his business associate pay a very high price for their life in the fast lane. Father the restaurant owner as well as the actress/model's father the driver have played safe, fearing excessive risk, while living modest lives. They are the Cassandras. Although Angela's father's character has not been developed to this extent his risk aversion and fears about his daughter's future were mentioned to Ian who ironically received this concern but said nothing. At the end the body count is three dead, one still on the loose.
As "Dream" ends we are left to consider the impact of this fallout upon surviving relatives and friends who, like the police, will ask "How could this horrible tragedy have happened?" The actual downward progression began during the boys early childhood.
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