-In his last trio of films —Match Point, Scoop and now Cassandra's Dream—Woody Allen seems hellbent on exploring the darkest human emotions: greed, selfish desire, a disregard for human life and how far one will go in the pursuit of superficial happiness. 
-Cassandra's Dream is different from most of his work in that the key relationship is not between a man and a woman, but between the two brothers. "I wanted to make the main plot between men," Woody said. 
-Woody Allen: "So it comes through the fact that I grew up in a society and a culture where those who preached to us said that crime didn't pay and that the bad guy always wound up trapped in the end and the good guy triumphed. And I think, yes, life would be wonderful if it was that way, but it was clear to me that life was not that way. So I always felt that, barring a heaven and a hell — a religious solution, which I did not believe in — and barring the fact that the bad guy does not always get caught, the only thing you have is your own sense of morality. If it doesn't bother you to commit a crime, then it doesn't bother you. And if you get away with it, you get away with it. It's not like a fairy tale; there is no penalty. Everyday we see crimes ranging from sleazy little ones in the street like drug deals, to white collar crimes and governmental crimes on the national level. And people get away with it. There are some people in the government, some people in the streets — wherever — who have consciences and that's the only thing that saves them, but some do not. I was interested in those stories — and the stories mostly of those who do not because they have more tension, more conflict, and a more intellectual argument about morality." 
Two London brothers are hard-up for cash, and both have girls to look out for, too. When rich Uncle Howard comes to town and agrees to help them out, he admits his finances are under investigation, and he asks them to do him a favor and "take care of" an old business relation to keep his trouble under wraps - he says that they're family, and since he always takes care of them, the least they could do is help him out this once, as they're the only ones he can trust. The film follows their struggle with the immorality of this request and how each brother chooses to deal with it. 
-Cassandra's Dream is a continuation of a premise that began with Crimes and Misdemeanors (1989) and continued with Match Point (2005). In all three films, the protagonists are driven to murder for the purpose of self-preservation, and in all three films it is evil that triumphs over good. Cassandra's Dream - with its parallel themes of moral corruption and exploitation - is arguably the bleakest of the three, if not the bleakest film of Allen's career thus far. Whereas before, an audience could have expected the charm of his characters or the natural wit of his dialog to dilute or detract from the heavy sense of dread that plagues these stories of crime without punishment, the general tone of Cassandra's Dream is that of almost unremitting despair. 
-One of the ideas Allen likes to keep circling back upon is the heavily ironic notion that it is perfectly possible — literally — to get away with murder, totally unpunished, in the godless and amoral modern world. It is the theme of two of his best films, Crimes and Misdemeanors and Match Point, and it is a central element in this movie. Like the protagonists of those earlier films, the brothers are not inherently evil people. They're just rather careless ones. Or perhaps one should say ungrounded. 
-[Cassandra's Dream] takes Allen into emotional territory he has not fully explored in his previous reflections on capital crimes. Which is not to say that Cassandra's Dream is quite the breakthrough film I think it might have been. It is a talkative film, rather earnest in its tonalities, not at all a deft, witty or well-paced. On the other hand, it is, for Allen, a comparatively rare excursion into lower-class life — the setting is London, as it has been in his two previous films — and its portrayal of the contortions upward striving can impose on people eager to move up in class is cool, well-observed and often even touching..." 
-Cassandra's Dream is much more tough-minded. And much less immediately appealing. I walked out of the screening admiring it, but not deeply moved. Yet the movie has stayed with me as a lot of the more heralded year-end films have not. There was a time in his career when Allen's lurches toward seriousness seemed to a lot of people unearned. He himself satirized that take on those films as early as 1980's Stardust Memories. But he's over 70 now — difficult as that is for some of us to believe — and he has fully earned the right to address us in any voice he chooses. Here its volume is turned down low. But if you lean in a bit you can hear it saying intricate and interesting things about the way class, character and morality operate in a realistically rendered milieu that is new for him and, in the context of this movie moment, quite gripping for us. 
He was right about one thing. Once you cross the line, there's no going back.
-Woody Allen, "You figure out the location and the lighting to complement the theme and the effect of the scene that you want. When I was saying “lazy,” I actually meant it. For example, there is a long scene with the brothers and the uncle set under a tree. Now that was a very long scene if you look at the script — it's many pages of dialogue. Somebody else — and very effectively, as well — could have shot the uncle, and Colin [Farrell] and then Ewan [McGregor], then over the shoulder of Ewan and then over the shoulder of Colin, all different combinations. They could have worked on that thing for two days. I didn't; I started the camera once, and dollied around the trees and filmed seven pages of the scene before I was forced to get into some cutting. And I do that out of laziness because I don't have the patience to make the actors do it or to do it myself — shooting the scene, and then shooting the same material again, and then shooting the same material again on the other actor and shooting it again over-the-shoulder and shooting it again, over and over, so that you're constantly droning on doing the same scene over and over all day. I can't do that. I choreograph so I can get everything in early in the day and at, say, two in the afternoon, we'll shoot. We cover seven pages in one shot and maybe the first time they screw it up, but by the second take or the third take, they've got it, and I get the whole scene. The actors appreciate it; they don't have to do it endlessly. They can sink their teeth into some acting for seven pages instead of doing one line before a cut — that's not acting. It's worked out very well for me, but the convenience of it is that I'm lazy." 
-McGregor and Farrell both praised Allen fulsomely, but their accounts of working with him hint at why, perhaps, Cassandra's Dream seemed so under-realised. To put it bluntly, Allen may have made the film too quickly and too easily. "Most of the scenes play out in a single frame," McGregor explained. "There is a lot of dialogue. There are not many takes – it's wonderful. You get home at 4.30pm in the afternoon. You can have a life." 
-Colin Farrell said in an interview that he "think[s] [he] did as many takes for this whole film as I did for one scene in Miami Vice." 
Any time Woody Allen releases a new film, moviegoers naturally debate where it ranks on his filmography. Is it a triumphant return to form...? Is it a vibrant echo of his early masterpieces, or a dispiriting reminder that he’s now 76 and his best years may be behind him? There’s rarely a middle ground: It’s either Good Woody or Bad Woody. 
When it first opened in 2007, the reviews for Cassandra's Dream suggested that it was Bad Woody — that, following 2005’s triumphant Match Point, this thriller, starring Ewan McGregor and Colin Farrell as two brothers whose financial woes lead them to accept a sinister request from their rich uncle, was a disappointment. But I loved it at the time, finding it unusually gripping and surprisingly poignant. I may have even liked it more than Match Point, which was acknowledged by many [in the US] as a late, cold-hearted masterpiece. 
-Here’s a prediction: Years from now, we’ll think of Woody Allen’s films the same way we think of Alfred Hitchcock’s films, or, for that matter, Shakespeare’s plays — as a remarkable, unified body of work. Yes, there may be peaks and valleys, but it’s all Hitchcock, or Shakespeare, and even the least significant part of the oeuvre engages on a distinctive level. We’re already seeing some of this happen. By most contemporary standards, Allen’s films in the 1980s and early 1990s were a mixed bag: For every Oscar-nominated Hannah and Her Sisters, there was at least one disappointment like Another Woman, or an outright flop like Shadows and Fog or September. And yet, today, many of those films that were written off at the time are now being rediscovered...But ultimately, there won’t be Good Woody or Bad Woody. It will all just be Woody, irreplaceable and inimitable. 
-Woody Allen: "Well, [people's opinions] can’t concern you. Because if it concerns you, then what happens is, it paralyzes you and you sit home trying to anticipate what they’re going to like. And you make a step and then you panic and think, “No, that’s not it.” So you’ve just got to do what you want to do, and hope that they like it. That’s always been the way that I worked; I always made whatever I’ve wanted, whether it was a musical or a black-and-white film or a Bergmanesque drama. Whatever strikes me as interesting at that time, that’s what I make. And I hope the audience likes it. If they don’t like it, there’s nothing I can do about it; I’m off on the next one. If they do like it, that’s always nice. The position you don’t want to be in is, you want to like the film yourself, and if you make the film and you yourself don’t like it…I write the script and then direct, and if I don’t like what I’ve done when it’s over, then even if the audience likes it, I figure, “Well, I got away with one” or “They’re not perceptive” or “This is such a piece of junk” – so it’s not a good feeling. But if you make a film that you like – “This is really a good piece of work; I got the most out of this script and executed it beautifully” – and they like it, it’s great. But if they don’t like it, you still get somewhat of a decent feeling. You figure, “Well, it’s a bad break for me, they don’t like it; but I really did the best job I could and I’m sorry they don’t like it.” That’s a much better feeling than if they love it and you yourself don’t get any kick out of it." 
-Colin Farrell on how he prepared with Ewan McGregor for the role of two brothers, "We went bowling. And go-cart racin’. No, seriously, we didn’t do anything. I went over to his house in London and we shot the breeze and talked about what it might have been like for these two brothers growing up, you know, tried to find a basis for understanding between them, what the status was in their relationship. Who is the provider and who was the receiver? Just how they related, in broad strokes." 
-Unusually for a Woody Allen film, the music is provided by a composer - in this case, Philip Glass - instead of being a collection of old standards. 
-The third consecutive Woody Allen film to be made in the UK (after Match Point and Scoop), and the first one not to have any Americans in the cast. 
-When Woody Allen first approached Philip Glass about doing the film's score, they had an initial meeting in which Glass played him a particularly ominous piece of music. Allen remarked that it was a very heavy section of music and that it would be perfect for establishing the dark mood of the film. Glass interjected with the fact that the music he'd just played was actually the love theme and he hadn't gotten round to writing anything ominous yet! 
-Sally Hawkins dyed her hair blonde for the film. 
-This is the first Woody Allen film to be released with a stereo soundtrack. 
-Like Melinda and Melinda, this movie’s worldwide release spanned a calendar year, which is why it’s sometimes listed as 2007, sometimes as 2008. It played in the Toronto Film Festival and in a few European countries in 2007 but didn’t see general release in the UK or US until 2008. 
-Originally this was scheduled to open in late 2007 to qualify for Academy Award consideration. After some indifferent previews however, it was given a January 2008 release, traditionally the dumping ground for bad films. 
-Woody described the movie's January release as "[putting] the film into a witness protection program.”
-The London restaurant Claridges, referred to several times and featured in the movie, is owned by chef Gordon Ramsay of television fame. 
-Wanna see what this film could have been? Many critics (including Roger Ebert) suggest watching Sidney Lumet's "Before the Devil Knows You're Dead."
Nobody wants to be selfish, but everybody is.
After all I've done for you, it should be automatic. Family is family! Blood is blood! You don't ask questions. You protect your own.
-Richard Brody of The New Yorker listed Cassandra’s Dream as one of the best films of the 2000s. "Few aging directors so cogently and relentlessly depict the grimly destructive machinery of life, and every time the word “family” is uttered, the screws tighten just a little more."
-Manohla Dargis of The New York Times wrote, “Cassandra’s Dream,” Woody Allen’s latest excursion to the dark side of human nature, is good enough that you may wonder why he doesn’t just stop making comedies once and for all. Like all filmmakers, Mr. Allen steals from himself like a magpie, which wouldn’t be grounds for criticism if he were a more dedicated and careful thief. Like many of his later films, though, “Cassandra’s Dream” feels too lightly polished and often rushed, as if he had directed it with a stopwatch. That’s too bad, because while Mr. Allen may feel as if he’s running out of time, he has scarcely run out of ideas.
-Michael Phillips for the Chicago Tribune wrote, As we know by now, Allen is obsessed with the notion of getting away with murder, mullingover which personalities can shoulder the psychological burden of killing without remorse, while others crumble under the pressure. The problem is, you don't feel the human sweat and strain in "Cassandra's Dream," despite game work from Farrell and McGregor. There are plenty of ideas and themes and no people of distinctive interest to enliven them. The narrative plods along, and when Ian falls for a callow young actress (Hayley Atwell), you can't help but think: Haven't we been down this path just two Woody Allen films ago?
-Derek Elly for Variety wrote, "Like a tragic overture played at the wrong tempo and slightly off-key, Woody Allen’s London-set “Cassandra’s Dream” sends out more mixed signals than an inebriated telegraphist. On the face of it a “serious Woody,” following two brothers embroiled in murder, pic is actually a low-key, bumpy black comedy whose humor stems from the perhaps deliberate awkwardness of the characterizations and dialogue. A relatively easy sit, thanks to energetic perfs by Ewan McGregor and Colin Farrell, pic still fails to satisfy fully on any level."
-Every Woody Allen Movie website critic Trevor Gilks wrote: "Being able to make a movie is a dream come true for most directors, but for Woody Allen these days, it’s somewhere between a hobby and a chore. Cassandra’s Dream is a competent film, but depressingly indifferent. It’s the exact opposite of a passion project. Scoop was an equally lifeless movie, but as I’ve said countless times, Allen is gifted enough that he can get away with sleepwalking through comedy. For something with the dry, depressing content of Cassandra’s Dream, Allen needs to actually make an effort, as he did with Match Point, or else the result is unforgivably dull. Back when I was writing about Crimes and Misdemeanors, I found myself burdened with the task of doing its brilliance justice. The tables have turned, now — instead of feeling unworthy of Woody Allen’s movies, Woody Allen’s movies increasingly feel unworthy of the time it takes to watch them." 
-Light in the Dusk wrote: "Although the film works incredibly well as a conventional thriller, or perhaps even as a continuation of the theme explored in the two films previously mentioned, the best way to approach Cassandra's Dream, in my opinion, is as a film about ideas. A film where the relationships between characters or the references to certain literary standards, is continually suggesting new ways of looking at these scenes, or other potential stories that are suggested beyond the more conventional crime/drama narrative." 
-Cassandra's Dream has a 46% Rotten Tomatoes rating as of 2021.