While he is most well-regarded for his irreverent, often verbose philosophical comedies that offer sharp criticisms of the human condition, Woody Allen has never been afraid to take a few risks when they are most appropriate. There came a point in his career where he started to experiment with genre, particularly making films in which the comedic sheen was absent, replaced instead with a more dramatic approach that contained many fascinating details that showed he was just as brilliant a filmmaker when it comes to more serious material. However, there are a couple of these experiments that did not work out particularly well, as we can see in Cassandra’s Dream, which finds Allen returning to the United Kingdom to tell the story of two brothers who find themselves in a precarious position when a wealthy relative offers to pay off their gambling debts, with the caveat that they return the favour by killing the man who is about to testify against him in court. A story of existential conflict amongst the working class, the film has many great ideas, but unfortunately falls apart midway through, never quite being able to recover from what is a few misguided attempts at sobering drama. Two years previously, Allen had made the well-received Match Point, which found him working with much more serious material, and was appropriately heralded as one of his most intriguing attempts at playing with tone and atmosphere. He attempts to recreate this sensation in Cassandra’s Dream, which is not strong enough as a story, not interesting enough in how it approaches its ideas, to be all that successful, instead working as a servicable, middle-of-the-road psychological drama that does everything we would expect, but in a way that still somehow feels like a bundle of missed opportunities from a director who is usually brilliant, but who is more than entitled to have a couple of missteps in his storied career.

Had you presented the first act of Cassandra’s Dream and labelled it as a Mike Leigh film, I would wholeheartedly believe it as being something he directed, a lesser work by all means but still very much in his wheelhouse? Allen is a director who knows how to draw influence from other filmmakers, so it would not be surprising if he was aiming to make his version of what he imagined the great British auteur would produce had he told this story. This is neither to diminish Leigh’s style as easily imitable, nor to position Allen as a mimic, but rather to point to the fact that this film is primarily a gritty, social realist crime drama set within the working-class population of London, exploring their experiences, focusing on two brothers who find themselves challenged beyond their wildest expectations, and whose relationship is put to the test in unexpected ways, which ultimately leads to quite a brutal conclusion. There is something amiss about this film, a feeling of danger that is not entirely earned or even all that impressive, but yet functions as one of the many aspects that drive this film and make it so intriguing in theory. It falls apart when it realises that it can’t weaponize these interesting elements for long, instead having to constantly shift between different plot points in order to give off the illusion of being a fast-paced thriller, when in reality it is very thinly-written, being based around a singular, one-sentence premise that has potential, but not enough complexity to actually justify some of the wackier decisions made in this film, particularly in terms of the character development, which is almost non-existent throughout this film, at least in the sense that it continuously struggles to develop its own identity beyond being a relatively conventional work that doesn’t offer anything we have not seen before in other gritty crime dramas, to which Allen was paying homage throughout this film, just not in a particularly memorable way.

Had Cassandra’s Dream ended about 15 minutes earlier, or just been focused on the ideas introduced in the first act, there is very little doubt that it would be seen as a much stronger film.  Allen has never been a filmmaker who has been known to overstay his welcome – he has made very few films that reach the two-hour mark, and has been known to be willing to make something that clocks in at a neat 90 minutes, making him one of the most economic filmmakers in terms of balancing content and time. This film is not particularly long, but it feels like a chore, primarily because of the pacing issues, as well as the tone – it often feels extremely jagged and inconsistent and seems to struggle in terms of choosing a specific atmosphere from which it builds the story. Even just in terms of genre, the film isn’t sure what it wants to be – at times, it seems to aim to become a darkly comedic exploration of the exploits of two bumbling fools tasked with an impossible task, while in others it seems to be paying tribute to the gritty British gangster films about ordinary people seeking for redemption after becoming intertwined in a life of crime. Unfortunately, the contrast does not work for this film – it is an inconsistent bundle of ideas that amounts to very little and is only compelling in the areas where it puts in the effort to develop itself beyond the simple premise. It does have promise, just not anything that emerges as being particularly worth our time, which is the tragic downfall of Cassandra’s Dream, a film with a lot of sincerity but not enough intelligence to tackle these subjects with anything close to the level of complexity they warranted, which is why the fact that it is an Allen production is so bewildering since there aren’t any traces of his distinctive style or mastery of the craft anywhere to be found throughout this unreliable and often quite frustrating film.

At the heart of Cassandra’s Dream we have performances from Colin Farrell and Ewan McGregor, who were certainly at the peak of their talents at this point (although both have worked consistently for over two decades now, so to suggest that they weren’t always delivering exceptional work is factually untrue), and were likely cast as a way of banking on their popularity, as well as giving them the gravitas of working with an auteur like Allen, who has always shown a fondness for adding new actors to his coterie of performers, many terrific performers managing to deliver exceptional work under his direction. Unfortunately, this film proves to be just another decent performance for both actors – they are objectively gifted, and do what was required of them, but not much more. Outside of the accents seeming quite shaky (casting a Scotsman and Irishman as not only members of the English working-class, but as brothers, seems to be a peculiar decision, and I can’t honestly say they are all that convincing), they turn in solid work, albeit not the kind that feels all that exciting or as if we are seeing a new side of this already very popular actors. Allen, unfortunately, misses the opportunity to have them doing exceptional, unexpected work – credit is warranted in choosing to make McGregor the more bloodthirsty of the two since one would expect Farrell and his more rugged, rough-around-the-edges persona to be the more violent of the two, but outside of a few intriguing details, there’s nothing about this film that warrants our attention or admiration in any significant way. We also find that this film doesn’t give too much to the supporting cast – Tom Wilkinson is obviously the best of the group (as well as turning in the best performance in the film, seemingly being the only person who found the right approach), but Hayley Atwell and Sally Hawkins are both wasted, and we never truly get to know them, which is very odd for a director who has been quite forthright in how he commits himself to writing female roles, rendering them essentially non-existent throughout this film, despite their impact on the narrative, which makes us wonder how different the film could have been with a better approach.

When a filmmaker builds their reputation as someone capable of making a new film every year, it is hardly surprising that some of them would be less successful than others. Cassandra’s Dream is by no means Allen’s worst film, and it doesn’t even occupy a space in the lower tier, simply being too dull to even warrant that level of disdain to be at the bottom of his career. It sits squarely in the middle – being bold enough an experiment to warrant some attention, but lacking any real substance to maintain it, which is something that happens to many prolific directors. It isn’t a surprise that this would be the last time Allen tried to make this kind of overly dramatic psychological thriller for many years (with his return coming this year in the form of Coup de Grace, which is his first foreign-language film, and a return to this kind of seductive, dramatic European drama), since it was not something with which he was either well-versed or even all that interested in exploring outside of the very obvious elements that would draw him to this kind of story. As a whole, Cassandra’s Dream has some very interesting moments – it provides a very different kind of perspective on the working class, filtering social commentary through a simple but effective story of two young men who are desperate for some escape, and find themselves growing increasingly more paranoid, going to extraordinary lengths to make their way out of the awful situation in which they find themselves. It may have pacing issues and the tone is extremely inconsistent, but it still manages to be a passable effort, a layered and provocative series of moments that don’t amount to much in the grander scheme of the narrative, but at least keep us entertained. Neither defining nor destructive to his directorial career, Cassandra’s Dream finds Allen doing something quite different, and whether it was because he believed in this story or simply wanted it out of his system, the results are average at best, proving to be yet another passable but otherwise forgettable entry into his long career.