The film takes its name from the Rolling Stones song of the same name. The film's original title was Baby's in Black, and then later changed to Goodbye Hello, and then the current title. The film is set in 1973 and music from that era is heavily featured, including that of the Rolling Stones, Van Morrison, Bob Dylan, and Elton John.
Following the murder of Diana Floss (Careena Melia) in a restaurant shooting in Cape Ann, Massachusetts in 1973, her fiancé Joe Nast (Jake Gyllenhaal) elects to stay with her parents. Her father Ben Floss (Dustin Hoffman) is a realtor whose business partner has recently left. Ben and Joe go into business as Floss & Son, as this was their plan before Diana's death. Joe goes to the post office to retrieve all the invitations that had been sent out for his and Diana's wedding, and with the help of Bertie Knox (Ellen Pompeo) he retrieves seventy-four of seventy-five. She finds the last invitation and takes it to his house later that night. He drops her off at a local bar, and returns home, despite her inviting him in for a drink. Joe and Ben attend a local property fair, and Ben pitches the idea of redeveloping a block in the town to developer Mike Mulcahey (Dabney Coleman). Mulcahey agrees, but they need to get all the tenants to agree.
Diana's friends come around to look through her possessions, much to the consternation of her mother Jojo (Susan Sarandon). They then take Joe out for a drink at the same bar Bertie went into the previous night. Joe puts "Moonlight Mile" on the jukebox and Bertie dances with him, to jealous looks from Diana's friends. Joe convinces Ben to let him talk to the bar's owner to convince them to sell. He asks the bartender who owns the bar, but the bartender does not give him the information. Feeling trapped at the Floss home, he meets Bertie and tells her about Diana. He confesses to her that he had split up with Diana three days before she was killed. Bertie tells Joe about her boyfriend, the owner of the bar, who is lost in Vietnam.
The house becomes more tense, and one night Joe sneaks out of the window to go see Bertie again. They sleep together, and he leaves the next morning, slipping back into Diana's house through the window. When he enters the room, Jojo is sitting there drinking, knowing that he has gone out to see another woman, and saddened by the idea that she had always known he would have never truly ended up with her daughter. She does not want Joe to leave, as they have formed a strong bond.
Joe goes to dinner at the Mulcahey's, where Mike's wife rudely presumes aloud that she thought Joe was not still tied up with thoughts of his fiancee's murder. Joe states that this is not the case, completely upsetting the mood at the dinner table. Mike calls Ben and end their deal.
Bertie confronts Joe about what happened between them, and they have an argument where he tells her no one believes her boyfriend is coming home and that she deserved better anyways. She leaves, upset. The family attends the trial of Diana's murderer. However, the murderer's wife elicits sympathy from the jury, and the prosecutor, Mona Camp (Holly Hunter), asks Joe to testify and help the jury gain sympathy for Diana. While on the witness stand, Joe confesses that he and Diana had broken up prior to her death, and had not told her parents. Ben and Jojo are happy with the confession and gain closure. Joe symbolically writes 75 letters expressing his newfound clarity about what course his life ought to take and his love for Bertie, and places them in mailboxes around town, hoping that one will get to her.
Ben closes the shop, Jojo resumes her writing career, Bertie sells the bar, and she and Joe leave town.Jake Gyllenhaal as Joe Nast
Dustin Hoffman as Ben Floss
Susan Sarandon as Jojo Floss
Ellen Pompeo as Bertie Knox
Holly Hunter as Mona Camp
Dabney Coleman as Mike Mulcahey
Careena Melia as Diana Floss
Roxanne Hart as June Mulcahey
Richard T. Jones as Ty
Phil Reeves and McNally Sagal as Mr. and Mrs. Don Tippet
Aleksia Landeau as Cheryl
Moonlight Mile was partially filmed on location in South Pasadena, California, Swampscott, Massachusetts, Marblehead, Massachusetts, the town common in Cohasset, Massachusetts, and Gloucester, Massachusetts. Neighbor's Restaurant is really Haley's Liquor Store in Marblehead.
The film grossed $10,011,050 worldwide from a $21 million budget.
Moonlight Mile received mixed reviews from critics: the review aggregator Rotten Tomatoes sampled 147 reviews, and gave the film a "63%" positive rating.
The Moonlight Mile soundtrack was released September 24, 2002 by Sony Records.
- "I Want to Take You Higher" - Sly & The Family Stone
- "Moonlight Mile" - The Rolling Stones
- "Love Will Come Through" - Travis
- "20th Century Boy" - T. Rex
- "Sweet Head" - David Bowie
- "Everybody Is a Star" - Sly and the Family Stone
- "I Hear You Knocking" - Dave Edmunds
- "Rock and Roll (Part 2)″ - Gary Glitter
- "Razor Face" - Elton John
- "I'll Be Your Lover Too" - Van Morrison
- "Comin' Back to Me" - Jefferson Airplane
- "Buckets of Rain" - Bob Dylan
- "Song to the Siren" - Robert Plant
- "The Telling" - Jorma Kaukonen