While such a setup might cause one to think that the film will be dark and heavy, Collateral Beauty is anything but. It has sad moments, but the glossy look of the film, the at times incongruously upbeat music (from Theodore Shapiro), and the actions of Howard's friends keep the whole train moving. It doesn't go in a good direction, but it keeps moving.
Collateral Beauty is a perplexing film, a movie that feels so excited to get to specific moments that it completely bypasses any logic on how such moments can be arrived at. The basic plot finds Howard's friends/co-workers – Whit (Edward Norton), Claire (Kate Winslet), and Simon (Michael Peña) hiring actors (played by Helen Mirren, Keira Knightley, and Jacob Latimore) who will help get Howard declared incompetent so that these friends can sell the company out from under him.
If that sounds distasteful, be warned, it gets worse because the actors are hired to play Death (Mirren), Time (Latimore), and Love (Knightley) as Howard has written letters to those three ideas in an attempt to heal. The plan is for these three actors to interact with Howard, have a private eye film it (the P.I. steals the letters from a mailbox in the first place), and then to have the actors digitally removed from the video (falsely portraying his insanity).
There are brief, unconvincing, attempts to explain why this doesn't make Whit, Claire, and Simon the worst human beings on the planet and there are moments when the actors question the roles. As a whole however, the movie wants the audience to believe that these people are doing the right thing, that the ends justify the means, and that if maybe Howard is pulled out of this funk by meeting Time, Death, and Love, that good has triumphed due to this abominable evil. Of course, Howard's friends don't really know how Howard is feeling because he won't talk to them, so this sort of thing could drive him over the edge once and for all (but then the company could be sold more easily).
The audience is also denied access to Howard's thoughts as very little time is spent with him until he starts getting visits from the actors. As Howard starts to talk to what he believes are figments of his imagination, the audience doesn't know whether this is truly him changing or simply more of the status quo. Things are made even more confusing as Howard stands outside a support group for parents who have lost children. As the group leader, Madeline (Naomie Harris), makes clear later, this is something he regularly does. Yet, for some reason, the private eye has not included it in reports on Howard's activity.
Part of the problem is that Collateral Beauty lacks focus. It isn't just about Howard's life and connections, it is about Whit's problems with his daughter and Claire's having worked so hard she never had a family and Simon's hiding an illness from his wife.
The film would have us believe it clever when Whit deals with the actress playing Love and Claire with Time and Simon with Death as the various friends' problems are mirrored in these ideas, but it is never fully developed, unearned, and obvious. One regularly gets the sense that Collateral Beauty is winking at the audience about its own cleverness, patting itself on the back at putting out an idea, rather than attempting to explore the idea it has started to unfurl.
For all the negatives in the film, it must be said that Knightley, Mirren, and Latimore are vibrant in their roles, giving Collateral Beauty depth which the dialogue (the screenplay is from Allan Loeb) might not deliver. Smith, too, is achingly good at moments, but again is let down by the script. In one scene he is riding a bicycle at night against traffic on a one-way street in New York City. While to some this may show the depths of his despair, a view which makes the actions of his friends that much more reprehensible, those who frequent the city might simply understand it as behaving in the same manner as the incredibly large number of cyclists who view one-way signs as suggestions not hard-and-fast rules. Whichever way then one chooses to see Howard's ride, just as with the rest of the film, it is a moment which doesn't necessarily convey the intended meaning.
Collateral Beauty is a movie that bypasses any well-meaning attempts on the part of Howard's friends to break him out of his depression. The audience is to understand that these things occurred in the past, but it doesn't show them, all it gives is the end game – a horrific money-grubbing attempt to have Howard declared incompetent. The movie then asks the audience to like the people who are doing this to their friend, accept some at best vague notion of a greater good coming from their actions, and sit in amazement at how all the various pieces of the story come together. More often than not it treats these elements as light drama, removing any punch the actions may have had and making the whole thing far more off-putting than it otherwise would be, and it would still be pretty off-putting.