The setting is a small Massachusetts town in 1972. Diana Floss has just been shot dead at the local diner - she was in the wrong place at the wrong time when a gunman attempted to kill his wife. Diana's soft-spoken fiancé Joe Nast (Jake Gyllenhaal) is living with her parents Jojo (Susan Sarandon), a writer, and Ben (Dustin Hoffman), a commercial real estate agent. They navigate the funeral and memorial service together, and meet with prosecutor Mona Camp (Holly Hunter) in preparation for the killer's trial.
Ben wants to move on quickly, and brings Joe in as his new business partner without much pause. They start working on a land assembly deal for big-time developer Mike Mulcahey (Dabney Coleman). But beneath his calm facade Joe is struggling with a couple of secrets: his relationship with Diana had already ended before she was killed; and he is starting to fall in love with Bertie Knox (Ellen Pompeo), who works at the post office and the local bar.
Writer and director Brad Silberling was dating actress Rebecca Schaeffer when she was murdered in 1989, and subsequently he lived for a while with her parents. Moonlight Mile is loosely inspired by his experience. The film adopts a pragmatic, almost detached, attitude towards the loss of a daughter and fiancée, avoiding histrionics but still finding patches of quiet anger, disbelief, and disorientation. Layered on top of the grief are observations about the long-term relationship between Jojo and Ben; Joe sensing entrapment within an unearned son-in-law status; and a burgeoning complex romance with Bertie, who is dealing with an unresolved loss of her own.The uniquely reflective mood challenges norms and ironically provides the drama with an edge. Jojo becomes snappy and her prose dries up, Ben drowns his emotions in work, but their mental state remains remarkably steady, their rage at losing Diana relatively subdued. Susan Sarandon and Dustin Hoffman stay within themselves as a couple well past expressing passion about anything.
Meanwhile Jake Gyllenhaal fills the screen with silent quandary as Joe defaults to present absenteeism in response to shock, guilt, and displacement. He harbours the awful truth about a breakup that now cannot be mentioned, and tags along as Ben unilaterally charts his future, all while hopelessly developing an attraction to Bertie.
The town with one main street is a comfortable cradle, and the 1970s setting is stealthy - the set design is unobtrusive, and only the car models and references to the Vietnam War reveal the era. More prominent is a unique music score featuring eccentric selections from the Stones, Dylan, Bowie, Jethro Tull, and Sly and the Family Stone among others.
Moonlight Mile navigates towards a standard truth-shall-set-you-free moment, but covers the distance with a quizzical attitude set to idiosyncratic tunes.
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