Moonlight Mile concerns Joe Nast (a miscast Jake Gyllenhaal), a young man whose fiancée is killed a month before their wedding. After attending his beloved's funeral, Joe stays on at the home of her parents, Ben and JoJo Floss (Dustin Hoffman and Susan Sarandon), partly because he is trying to fulfill his role as the grief-stricken would-be son-in-law and partly because he can't think of anything else to do. With no burning ambition of his own, Joe had agreed to settle down in Diana's sleepy little New England hometown and join his father-in-law's real-estate business. Ben sees no reason to change these plans just because his daughter has died.
Ben and JoJo deal with their daughter's death in vastly different ways. Ben shifts into denial mode, remaining defiantly upbeat, taking on new projects at work, and staying compulsively busy at home. JoJo hits the bottle, refuses to leave the house, and directs a steady stream of belligerent humor and sarcasm at anyone within range. The couple argue incessantly, unable to find solace in their mutual grief.
Stuck in the middle is Joe, who basically just continues to drift. Then unexpectedly, he meets Bertie Knox (relative newcomer Ellen Pompeo, who bears more than a passing resemblance to Renée Zellweger) and falls in love.
Bertie, conveniently enough, has her own tragic tale of love and loss. Her boyfriend Cal went missing in action in Vietnam several years ago, and while everyone else in town pretty much accepts that he is dead, Bertie refuses even to consider the possibility.
It is at this point that the audience starts scratching its collective head. Vietnam? Are we in a time warp? Then we notice a couple of small things, such as Sarandon winding her wristwatch, and a song by Jefferson Airplane, and we begin to suspect that, despite the lack of any clear clues, such as clothing, slang expressions, or architectural design, this story is set in the early 1970s. Apparently Silberling, who also wrote the screenplay, was so intent on his characters' whys and wherefores, he forgot about the when. To a really shocking degree, this film has absolutely no feel for its time period.
Aside from the fact that establishing a recognizable time and place seems a pretty fundamental part of any script, why should this matter? For one thing, it would help establish the characters in their milieu, which would then aid the audience in evaluating and understanding those characters. For another thing, by setting the story in 1973 but not placing it there in any significant way, the time period comes across as nothing but an expedient -- or is that "crass?" -- plot device. It proves wholly unconvincing. Bertie could have had any number of backstories that would have linked her more credibly with Joe.
Silberling, who apparently lost a loved one earlier in his own life, obviously sees himself in Joe. Unfortunately he identifies so closely with the character that he forgot other people also have to. Gyllenhaal, a wonderful actor, gives a surprisingly drab performance here, and he seems too immature for either Bertie or the little we learn about Diana. It would have been nice to get more of a sense of her. As it is, her death means nothing to us.
Hoffman is fine but it is Sarandon who walks away with the acting honors here, offering a totally believable portrait of a woman faced with the most terrible loss imaginable, the death of a child. JoJo's razor-sharp cynicism, bitchiness, and pain all feel real, and Sarandon conveys it without even a hint of overacting, a claim she can not always make. Her confrontations with Ben are as uncomfortable for the audience as they are for the characters.
The film takes an incredibly wrong turn when it shifts to the courtroom trial of the man who killed Diana (early scenes set up the case, with Holly Hunter in a small role as the Flosses' attorney). Here's the weepy, let's-all-get-honest part of the story that Silberling just can't seem to resist. It all but kills any goodwill he has engendered up to this point -- to say nothing of the fact that it conveys a very odd message to the film as a whole.