Genre: Crime/Drama
Director: Todd Field
Writer: Lon Charles
Cast: Matt Damon, Bryce Dallas Howard, Norbert Leo Butz, Cristin Milioti, Tequan Richmond, David Arquette, Mimi Rogers
Plot: Chucky Stewart (Matt Damon), general manager of Salas & Son furriers on chic Newbury St. in Boston. Chucky is in the middle of having sex with his assistant Debby Allen (Bryce Dallas Howard) on top of his office desk. The sales staff try to distract their high end clientele from the obvious noises of passion.
Chucky, drenched in post-coital sweat, realizes he is running late. He hurries out of his office, zipping up his pants on his way out the door. He speeds through the ever-congested roadways of the Back Bay area. He rushes into a building where his very angry, and very pregnant, wife Carol (Cristin Milioti) is waiting for him. She chastises him for being late. He blames the traffic, and together they head into a child birth class with other expectant couples.
Chucky picks up his brother Mark (Norbert Leo Butz) from prison where he was serving a sentence for drug trafficking. They hit the local bar, and the two get drunk in no time. Chucky asks Mark what his plan is now that he's back on the outside, but Mark hasn't figured anything out yet. Mark orders another beer and tries to avoid any more questions on his lack plans by bringing up how Chucky feels about becoming a father. Chucky is clearly not high on the concept and expresses to Mark that he bets Carol won't go back to work after the baby is born, leaving him as the sole earner in the household.
Chucky drunkenly drives home, Mark in tow. Chucky stumbles inside the house and asks Carol if Mark can stay with them until he gets back on his feet. She says she doesn't want a drug dealer around the house. He tries to explain that his brother isn't a dealer, just a trafficker, but she's not having any of it. Chucky starts yelling that he's the only one bringing home money anymore, so he gets more of a say than she does now. Carol goes into the bedroom, slamming the door. Chucky tries to follow her, but finds that she locked the bedroom door behind her. Chucky shrugs and helps Mark in from the car. Chucky practically drugs Mark to the couch. Chucky then turns on the TV and passes out in his favorite chair in front of a hairloss infomercial.
In the morning, Carol leaves to go run some errands without saying a word to Chucky or Mark. Once she's gone, Chucky tells Mark about a plan he has to rob the fur store he runs on Newbury Street that night and asks for Mark's help. He explains that he'll take the cash and bring it to Mark in the Mission Hill neighborhood, and then he will call the cops and tell them that he has been robbed at the store. Mark says that Chucky appears to be doing fine for himself and wonders why he would want to risk it all for a little extra money. Chucky explains that he is sick of working at the fur store and wants to finally open his own restaurant like he always wanted. He thinks that opening a restaurant will not only make him happier, but will also help reignite his marriage to Carol since they met when they worked at a restaurant together in college. Mark agrees to help since it's for such a noble cause.
Chucky is at work at Salas & Son. Business is slow that day, so Chucky and Debby have sex in the office. Afterwards, they discuss going on a trip together. Debby is worried how it would work with Chucky having a baby on the way, but he says not to worry about it, that he's expecting to have some time on his hands soon enough. Their conversation is cut short by a customer entering the store.
Chucky and Carol are in child birthing class again that night. Carol is still clearly mad at Chucky and Chucky is clearly bored being there. They get into the car and sit in silence as Chucky starts to drive through the Mission Hill area of Boston.
Chucky screaches his car to a stop at the entrance to the emergency room. He's been shot in the stomach. He falls out of the car, passing out from bloodloss. Carol sits lifeless in the passenger seat, a bullet hole in her head.
When Chucky comes to a Boston Police Detective Al Pilozzi (David Arquette) is waiting to talk to him. Pilozzi asks Chucky if he can recount the events that led to the death of his wife and his unborn baby. Chucky begins crying, saying nobody told him they were both dead. Chucky, in his anguish, tries to get up from his hospital bed, but collapses on the floor. Nurses rush to his aid and help him back into bed. A doctor gives Chucky a mild sedative. Once he's calmed down a bit, Chucky gives Detective Pilozzi a detailed account of a young black man forcing his way into the car, making them drive to the Mission Hill neighborhood and stealing their jewelry and money.
Detective Pilozzi supervises stop and frisk searches of scores of young black males after the Mayor of Boston announces to the public that he will make sure the responsible party is found and that justice will be swift and merciless. Pilozzi calls in the information on one of the young men he is searching, and dispatch reports that the man, Willis Bennett (Tequan Richmond) had recently been charged with robbing a video store. When Pilozzi brings Bennett downtown to the station, he is informed that Bennett was reportedly seen with a gun and some jewelry in the Mission Hill area and that he has allegedly boasted about killing "the white woman from the news". Pilozzi can't believe his luck. The most wanted criminal in Boston has just fallen into his lap.
Chucky is just getting out of surgery when he is informed by Pilozzi that they may have found the attacker and would like for him to come down to the station to see if he can pick him out of a lineup. Chucky is wheeled to the police station by his brother Mark and his mother-in-law Barbara (Mimi Rogers). At the station, Chucky, still in a wheelchair, carefully studies the police lineup at the station. Pilozzi asks him if he can identify the attacker. He says that Bennett looks the most like his attacker, but isn't 100% sure. Pilozzi thanks Chucky for his time.
Back at his desk, Pilozzi answers a phone call. The person on the other line says they heard a rumor that Chucky Stewart killed his own wife. Pilozzi isn't buying it, and hangs up, assuming it's just a prank call from someone else in the department.
Chucky is back at his house. He calls Debby and invites her over. She arrives, but feels weird being in the same house he shared with his wife. Chucky tells her that she knows he didn't love Carol anymore. He then tells her that the night Carol was murdered he had just asked her for a divorce and she had agreed. He was still willing to be a part of the baby's life, but he told her that he was in love with Debby and wanted to be with her. Debby is touched by this sentiment and begins kissing Chucky. She begins undoing his pants, but Mark walks in on them, ruining the mood. Debby kisses him goodnight.
Barbara and her two Jack Russell terriers come to check on how Chucky is feeling. Her dogs starts attacking Chucky's leg. Barbara scolds the dogs and puts them out in the yard. She apologizes to Chucky, saying they usually only have problems with bad guys and mail carriers. Chucky says it's okay. Dogs can make mistakes too. He then jokes that maybe they thought he joined the USPS.
Mark goes downtown and scores some heroin at a dive bar. He shoots up in the bathroom and wanders down the streets of Boston. He stumbles and falls down on the sidewalk. When he looks up, he notices that he's out in front of the police station. He goes inside and says he has information regarding a murder. He is eventually taken into an interview room where he is greeted by Detective Pilozzi. Mark breaks down in the room, confessing that his brother Chucky killed his wife Carol. Pilozzi is surprised to hear this and asks for more information. Mark explains that he was supposed to meet Chucky in Mission Hill and collect some money from the fur store, but instead Chucky was covered in blood and handed him Carol's purse and jewelry and told him to get rid of it. Marky says he did as his brother asked since Chucky has always looked out for him. Mark tells Pilozzi he needs to make a phone call. Mark then calls Chucky and simply says he's sorry before hanging up.
Chucky, in a panic, packs a bag and gets in his car. He hits an ATM and withdraws as much cash as it will give him. It's only $200. Chucky curses his luck under his breath and runs away from the ATM.
Pilozzi immediately orders a squad car to go pick up Chucky at his home. When the cops break down the door and enter the house, they find Debby in lingerie. She tells them she was waiting for Chucky and that they had plans that night. The officers radio Pilozzi and tell him that Chucky isn't there, but his mistress is. Pilozzi tells them to bring Debby in for questioning.
Chucky sits in a motel room in the suburbs trying to mull over his options. Surely the police would be monitoring his bank accounts by now, and he couldn't find his passport - not that he had enough cash to start from scratch somewhere else. Chucky drinks as he watches coverage of his own manhunt on the news. Resigned to his fate, Chucky drives out to the Tobin Bridge and jumps the 135 feet down into the Mystic River below.
Pilozzi has Mark, Debby and Willis Bennett all released at the same time. They all look at each other and all walk in different directions away from the station.
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