The movie begins as Montgomery "Monty" Brogan (Edward Norton) is driving in New York City with Kostya (Tony Siraguza), his Ukrainian mobster-type muscle. Kostya has a heavy accent and some trouble with English idioms. He references "Doyle's Law" rather than Murphy's Law. While they're running late to meet with some "important people," they happen upon a badly injured dog that was obviously abandoned after a dogfight, and Monty wants to first shoot the dog with Kostya's gun as a mercy killing, but decides to save him instead, impressed by the dog's resilience. He grabs the dog in his jacket, and sticks it in his trunk, and though the dog bites him, he's very impressed with that fighting spirit. They drive on.Monty is sitting on a bench at the pier with the dog, now recuperated from his wounds, whom he named Doyle. It's early morning; people are jogging. Monty is approached by strung-out junkie begging for a fix, and Monty tells him to go to Harlem, because he's been "touched" and is out of the business. The junkie just doesn't seem to get it, says he's been coming to Monty for 5 years and that he'll remember this! He lurches off, and Monty wanders away with Doyle.Monty and Doyle walk along the streets of New York, and end up on the campus of what looks like a private prep school. Monty stands looking at a display of sports trophies and old photos, until a school administrator confronts him and tells him to leave with the dog. He tells her that he used to go to this school, and was on the basketball team, was doing well until he was kicked out of the school for fighting. She thaws a little bit as he shows her himself in the photo and says he held some big record. She tells him that record was broken just last year, and she knows because she coaches the girls' team. He's a little taken aback. He asks if she could help him find Jake Elinsky, his friend.In a classroom, Jakob "Jake" Elinsky (Philip Seymour Hoffman) is teaching his poetry class. The chairs are all arranged in a circle. One of the students, Mary (Anna Paquin) is reading a poem aloud to the class. She is dressed in a crop top revealing a large henna tattoo around her navel. The rest of the class seems like they're completely dead/disinterested.Just then, Monty shows up at the door and briefly talks to Jake. He tells him to get in touch with Frank and that they can't meet for dinner because he has to go see his dad. That they should meet afterwards at a bar and then there's a "going away" party for him that night at the Bridge club. He notes that Mary's appearance and that she's giving him the eye. He leaves and the bell rings; the students all scatter.Mary comes to see Jake in the teacher's lounge to ask about her grade. Mary argues about the unfair B- grade that he gave her on her last assignment, saying she needs better grades to get into college. She notes he gave another student an A+ for a story about his dead grandmother, despite it being low-effort. He diverts the conversation by asking about her tattoo and she implies that her mother doesn't really care what she does. The conversation resolves with Mary asking again if Jakob will change her grade, him stating he won't, and Mary angrily storming out.Francis "Frank" Xavier Slattery (Barry Pepper), a trader on Wall Street, receives a call from Jake, but quickly hangs up to attend to the hustle and bustle of his investment bank. Frank's boss comes and reprimands him that he needs to sell contracts he has been holding onto. It's obvious that Frank has a very high pressure job and deals with a lot of money, but is on top of it all. He doesn't do what the boss asks, seemingly confident his plan will be a success. It looks like he was right not to sell the contracts, however, when the financial network broadcasting channel reveals the employment number as Frank leans back in his chair satisfied with the outcome.Monty and Doyle go home. Out on the stoop, Naturelle (Rosario Dawson), Monty's girlfriend, is waiting for him. She's been sitting there all day, worried when he was already gone when she woke up. He says he needed to get out. It's obvious that there's a lot of tension between them. She wants to know if they're going to spend any time together or what. He tells her about the party being thrown tonight for him by Uncle Nikolai, and she really doesn't want him to go, but he says he can hardly avoid it. She then has him open a jar of honey, and she eats it straight out of the jar with a spoon, which he calls "a nasty habit." They kiss, and she asks him to take a bath with her, but he declines.In a flashback, Monty and Naturelle are in the bath together, joking around about having kids and Monty teasing Nat for getting a tattoo of the Puerto Rican flag when she's lived her whole life in New York City. They are affectionate and intimate with one another.Someone knocks on the door and Nat gets out of the tub to answer it, thinking it might be her mom. Instead, she opens the door to a group of four DEA agents. Monty joins them and is told by Agent Flood (Isiah Whitlock Jr.) they have a warrant to search the apartment. It's obvious they know where what they're looking for is hidden, as none of the agents are searching very hard. One of the agents opens up the couch cushions, revealing large amounts of money and drugs. Agent Flood mocks Monty with his discovery, and the flashback ends.In the present, and Monty's sitting on the couch. Naturelle keeps bugging him about spending time together, but he remains irritable and aloof, asking her to be quiet while she begs him to have a real conversation with her. Monty tells her he has to go see his father and that he'll see her at the club later. He asks her to wear the silver dress, because that's how he wants to remember her, before he leaves the apartment.Outside, Kostya is waiting at the stoop admiring and cat-calling the female passerbys outside. Kostya reminds Monty about the party at the club being held tonight by Uncle Nikolai in his honor. Monty's wondering why people keep insisting he go to the party. He says he'll be there with Naturelle and some friends. Kostya says he shouldn't bring Naturelle and implies that she was the one who tipped off the DEA. Evidently, that is what everyone in their circle believes. Monty rejects this claim as absurd, but states he hasn't asked her. Monty goes off to have dinner with his dad. A shot shows Naturelle was listening in on the conversation from a window above.We next see Monty inside Brogan's, an Irish pub owned by his dad, James Brogan (Brian Cox). The pub is decorated with paraphernalia and an altar dedicated to New York City firefighters. The patrons at the pub are sparse.During their conversation, we discover that Monty's dad used to be a fireman and an alcoholic. It is also revealed that James evidently owed money to a man named Sal and Monty had been paying it off using money earned from his illicit activities. His mom died when Monty was only 11, and James blames himself for how things have turned out, lamenting his Monty didn't become a lawyer or a doctor instead of falling into criminal activity, but Monty assures him it wasn't his fault. Monty leaves the table to use the restroom.While in the bathroom, Monty looks in the mirror and sees that it's got "Fuck You" written on it. Monty begins an impassioned, enraged rant about just about everyone in New York and beyond: pan-handlers, Sikhs and Pakistani taxi drivers, the "Chelsea Boys" of Manhattan, Korean grocers, Russian mobsters, Hasidic Jews, Wall-Street brokers, Puerto Ricans, "Dumbinacans" (Dominicans), the Bensonhurst Italians of Brooklyn, Upper East Side wives of Manhattan, the "Uptown brothers," the NYPD, the Catholic church and Catholic priests, Jesus Christ, Osama Bin Laden, al-Qaeda, and radical fundamentalist as a montage shows clips of the people he is ranting about. He curses out his friends Frank and Jake, his girlfriend Naturelle, and his father James. In the end, he says, "Fuck you, Montgomery Brogan, you had it all and you threw it all away." He tries to wipe the "Fuck You" off the mirror, but it's painted on.He returns to the table and asks his dad if he trusts Nat. After some prodding, Monty notes what people have been saying about her and admits he is questioning whether she was the one who turned him in. He says he only really trusts his dad and Frank and Jake, his two oldest friends. He leaves to go meet Frank and Jake without finishing his dinner, and his dad says he'll come in the morning to drive him to the jail. Before he goes, his father gives him a family picture of a young Monty in a fireman's helmet, his father, and his late-mother, who named Monty after the American actor Montgomery Clift.Jake meets up with Frank at his apartment, which overlooks Ground Zero. The two men talk as they look down at the horrifying sight. Frank says that he has no intention of moving. The two men then discuss Monty while sitting by the window overlooking the site. Jake seems to think that after Monty gets out, they'll still be friends, but Frank tells him that it's going to be over. Frank believes they'll never see him again and that Monty deserves his punishment as a result of his crimes. Jake wonders what will happen to Doyle and wishes that Monty could take his beloved dog to jail with him. The scene ends with multiple shots of the construction workers and heavy equipment vehicles that were part of the clean-up at World Trade Center site.In another flashback, Monty is being interrogated in an interrogation room by the DEA agents from earlier, while Naturelle gets let go. The DEA agents try to rile Monty up by implying that she was the one who tipped them off about him. The conversation reveals Monty got kicked out of school for selling marijuana to other students. They explain to Monty that the Rockefeller Laws in the state of New York make possession of 1 kilogram of drugs a major felony which holds a fifteen-year minimum sentence if convicted for a first-time offense. They tempt him by proposing he can lessen his sentence if he cooperates and gives them information on Uncle Nikolai's operation, but he refuses and talks smack to the agents instead. The agents leave the room.Frank and Jakob then go over to a Chinese restaurant and converse over dinner. Frank tells Jake that Jake's in the 62nd percentile of all the city's bachelors, while he, Frank, is in the 99 percentile. Frank elaborates that while the criteria includes the money he makes, Jake has a trust fund and is ashamed of being a wealthy Jewish kid. Frank tells Jake that he also has chronic bad breath. Jake is annoyed at Frank's comments and points out that Frank's lack of table manners and dying of his hair. Frank notes that Monty is in the 0 percentile since he is going to jail. Another flashback shows Naturelle at the park with a friend, both in uniform, discussing their plan to skip practice to hang out instead. Monty meets up with a man in a suit, who gives him a number to call. Monty approaches Naturelle, asking to borrow Nat's lighter to burn the number. They start chatting and flirting, while Naturelle's friend leaves. A coy, but friendly Naturelle shares that she plays basketball and is on a scholarship, like he was. She also tells him she is eighteen, to Monty's satisfaction. Monty ends the conversation by telling her he will go see her play one day. Frank and Jake arrive at the bar where they wait Monty, still talking about their percentile rankings, which the cute female bartender is aware of. Jake starts telling Frank about his teacher "friend" who has is interested in pursuing a sixteen-year-old student of his. Frank, naturally, sees through this, and gives Jake a hard time about crushing on a student. Naturelle arrives at the bar, cutting off their conversation, wearing the silver dress Monty requested. They banter for a while at the bar, then Nat goes to the bathroom. Monty shows up and the bartender serves them free drinks and invites them all to her birthday party that weekend which elicits an awkward silence from the trio. They drink and then they all take off to the club where the going-away party is being held.There's a long line of mostly young people trying to get into the club, but Monty's group has VIP access through the backdoor. The bouncer tells Monty the long line is for the popular seventeen-year-old DJ Dusk, who is playing at the club. As the gang heads toward the back entrance, Mary spies Jake and runs up to him, surprised to see him in attendance for DJ Dusk's show. Monty approaches the two, and remembering Mary from earlier, invites her to join the group inside.Inside the club, champagne is served, the group cheers, and Mary drinks her glass down. She and Naturelle go and dance, while Frank goes upstairs for whiskey. Jake and Monty converse alone, and Jake conveys worry that somehow it'll get out that he brought Mary into the club and he will lose his job. Monty dismisses the idea, pours Jake a drink, and requests a toast. Jake fails to find the words to say, so Monty dedicates the toast to Doyle. He states Doyle was the best thing that has happened to him and expresses he would like Jake to have him. Jake accepts Monty's wishFrank comes back and then Kostya shows up. Kostya says it's time to go see Uncle Nikolai and he, Monty, and Frank start going upstairs. Monty asks for five minutes alone with Frank. He tells Frank that he had all these thoughts of going straight and investing the money with Frank's help, but he got greedy. Frank basically tells him the opposite of the stuff he had said to Jake. He tells Monty he's a fighter, that he's going to be OK, that when he gets out, he'll be there for him and they can start an Irish bar together. He assures Monty, telling him they've known each other since they were three and he has never once broken a promise to him. Monty says that is all true, but ultimately asserts that he won't be there for him tomorrow. He says he has a plan that might buy him some time and he makes Frank promise to help.In the meantime, a visibly intoxicated Mary comes back to see that Jake's nodding off at the table. She straddles Jake, waking him up by rubbing his hands across her body, but Jake pushes her away. When asks her to keep all this quiet, she responds with questioning the grade change from earlier. She asks him where the bathroom is and heads that way. After some initial hesitance to follow her, the likewise inebriated Jake goes up there and kisses her. They exchange looks, but say no words, and Jake leaves the bathroom.Meanwhile, Nat is at the club's bar with Frank, who is downing several drinks quickly. She asks him to look out for Monty tonight, make sure he doesn't hurt himself. The conversation progresses to Frank feeling guilt over having not stopped Monty from going further into his life of crime, but ultimately ends with Frank accusing Naturelle of using Monty for his money and betraying him. She slaps him and storms off. Jake comes to the bar and tells Frank he kissed Mary. Frank tells him to shut up and have another drink, saying that they can't leave yet because they have to be there for Monty.Monty and Kostya in the meantime are in a back room where Uncle Nikolai (Levani) and his goons are. Uncle Nikolai tells Monty about his first time in prison when he was fourteen-years-old. He tells him that Monty should find someone who's not being protected and beat them in front of the other prisoners, and that way seem like he's a little crazy, but still respectful of the right people. Nikolai and his henchmen make indirect threats at Monty's father, but Monty assures him he did not give information to the police.Nikolai then suddenly orders his henchmen to beat Kostya, revealing that only he and Naturelle knew where Monty's stash was. Nikolai tells Monty to kill him, but after questioning Kostya over his why he blamed Nat, Monty tells Nikolai to "do his own dirty work" and leaves without killing him. Nikolai reminds Monty to "survive" and as the door closes, the other Russian mobsters are beating Kostya.Monty, Frank, and Jake leave the club to go home and get Doyle. Monty asks if they don't mind staying out a little later to do something. Monty goes into the bedroom, where Naturelle is sleeping. He embraces her warmly and apologizes for the way he has acted with her. He says he'll come back, but there's "one last thing" he has to do first. He, and Frank, and Jake all go out walking by the river with Doyle.Then they go into the park and Monty calls in his favor to Frank. He wants Frank to "make him ugly" as a way to repulse the other prisoners from messing with him, but Frank refuses. They all start screaming at one another, and Monty tells Frank he knows he's wanted to slap some sense into him. Eventually, Jake gets in the middle, and Monty punches him. Frank begin punching Monty repeatedly while he is on the ground, disfiguring and bloodying his face. Jake is able to get Monty back to his feet while Frank cries in despair. Monty walks back to home alone,greeted by Naturelle, horrified to see him this way. She tries to get him cleaned up and wants him to go to the hospital, but he refuses.We see Frank sitting in the same spot by the river that Monty was earlier. Jake's walking with Doyle and gets some attention from a girl because of it.Monty's dad shows up to take him to jail, and Monty reluctantly agrees to go with him instead of going alone. He tells Nat she should forget about him and live her life, though she swears she'll wait for him. She gives him ice for his face, but he dumps it all out on his way down and gets into the car with his dad. Monty sees the smiling faces of many of the New Yorkers he repudiated in his rant as they drive away.As they drive up the turnpike, his dad offers to just keep driving. Over a montage of scenes of them driving out West, James tells Monty of how he can find some town out there in the desert, disappear, make a new life for himself. He'll never see him again, but he'll know his boy's OK. Eventually, maybe, Monty can be reunited with Naturelle, and they can have kids and someday, he can tell the kids about his earlier life and how close it came that this blissful life "almost didn't happen." The montage shows this playing out -- them driving through the desert, them drinking a final shot of whiskey together, Monty getting a new ID, a new job, reunited with Nat, the kids, and everything.And as the "almost didn't happen" is said in the voiceover, we cut back to the car and see that they're still driving up the turnpike towards the jail, as Monty gazes out the window.