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Zach Braff as Michael
Jacinda Barrett as Jenna
Casey Affleck as Chris
Rachel Bilson as Kim
Michael Weston as Izzy
Blythe Danner as Anna
Tom Wilkinson as Stephen
Eric Christian Olsen as Kenny
A nicely unsentimental look at modern relationships, "The Last Kiss" suffers a bit from haphazardness in its construction, but holds up through a strong cast and solid writing.
Michael (Zach Braff) has reached one of the great turning points in middle-class American life – his longtime girlfriend (Jacinda Barrett) has just discovered she's pregnant and he realizes he is about to settle down for good. Contrasted against the disintegrating relationships of two of his best friends (Casey Affleck, Michael Weston) and the comfortable bohemian life of another (Eric Christian Olsen) he suddenly begins to wonder if that's really what he wants.
A remake of an Italian film, "Last Kiss" is not the first film of this type and it doesn't say anything particularly original about the position, but what it does say it says well enough with some well-observed dialogue from writer Paul Haggis ("Crash") that goes along way to making Michael and Jenna's relationship feel real enough that what happens to it has some sort of consequence and disguises the fact that Michael is essentially a milquetoast who really just needs a good kick in the ass to get his head out of it.
Braff approaches the role with the same lazy charm he used in "Garden State" and to much the same affect. When a young co-ed from the local college (Rachel Bilson) begins to come on to him he sees a possible way out but is rightfully uncertain if he wants to take it or if he's just blowing his uncomfortability out of proportion, which he is. Jacinda Barrett finally gets a real role and makes a lot of it, and Tom Wilkinson is excellent as her subdued-but-not-unfeeling father. It's a role he's done before, but he does it very well and many of his scenes are the strongest in the film.
It would work better if it didn't seem so haphazard. It starts off as an ensemble, bouncing the different stories off one another in an actually interesting contrast, but soon settles down to focusing mostly on Michael with other actors disappearing for large sections of time, until eventually, when their stories are wrapped up, it comes as more of a surprise than anything else. There are lots of promising stories like Jenna's mother's (Blythe Danner) breakdown and revelation of an affair that are just not given enough time to really develop and build to anything. I get the feeling that large amounts of the film were trimmed out in order to find some sort of narrative device to drive it. It works well enough in individual pieces, but the sum of its parts don't work so well together and the disparity weakens the conclusion considerably, to the point where the director Goldwyn feels the need to end the film with a montage instead of a catharsis, hoping no one notices he's painted himself into a corner and can't get out of it. It also results in a strong supporting cast being largely wasted.
It's entertaining enough and often very wry but the lack of a solid structure makes "The Last Kiss" too weak to really amount to anything.