Bill Kincaid (Edward Norton) is lecturing his Latin class at Brown University about Socrates’ dialogues. He dismisses the class and then meets up with his student, Anne (Lucy DeVito). She is clearly smitten with him and asks if he wants to go to a movie. Bill declines and Anne begins to talk about a note she gave him written sexually in Latin. Bill makes it clear that he can’t cross that line, but Anne closes the door and recites Latin as she takes off her shirt and tries to straddle him. A coworker walks in and Bill is put in an awkward position. The coworker talks to Bill about his meeting with Harvard associates in the morning and Bill makes it clear it is just lunch. The coworker leaves skeptically without a word.
Brady Kincaid (Edward Norton) is down South lecturing two drug dealers who work for Pug Rothbaum about the drug business. Brady grows and sells all natural marijuana. He tells the drug dealers that he doesn’t want to sell hard drugs like cocaine or heroin or expand his sales across the south. His partner, Bolger (Tim Blake Nelson), stands by Brady but the associates make it clear that if Brady doesn’t expand, he will never be able to pay his debt to Rothbaum. Brady and Bolger go back to Brady’s barn which is full of pot, grown in a special hydroponic system. Bolger talks to Brady about paying off Rothbaum, and Brady tells him he will find a way.
Brady drives to the old folks home and visits his mother, Daisy (Susan Sarandon), and gives her a copy of Bill’s latest paper. Daisy talks about Brady and Bill’s father and how she imagines that he wanted to die while he was fighting in the battlefield. Brady tells her that he remembers his father being a heavy pot smoker and asks Daisy why she won’t live with him and his girlfriend, Colleen (Melanie Lynskey). Daisy asserts that she likes the independence and states that she doesn’t want to have to find a new residence when Brady gets killed or taken back to prison. Brady tells her that Colleen is pregnant. Daisy lectures Brady about how Brady managed to give up on his intellect and that despite having a higher IQ than Bill, he allowed himself to be second best. Brady tells Daisy that he’s comfortable as he is but he leaves her and goes to his car. He breaks down, punching the roof repeatedly. He lights up a joint to calm down.
At lunch, Bill talks with Dean Sorensen (Ty Burrell) and another associate professor. Dean Sorensen is impressed by Bill, who made his way up from humble beginnings to succeed in the Classics and wants to offer him a job at Harvard law in order to inject more philosophy into the curriculum. Bill doesn’t know how to respond but the professors tell him that it is the next logical step in Bill’s career.
Brady is watching Colleen do the dishes in their kitchen and asks how long he has until they can have sex. Pug Rothbaum calls Brady at his house, upsetting Colleen and Brady takes the call into another room. Pug yells at Brady and wants Brady and Bolger to go up and visit him. Brady calls Bolger and they agree to go up and see him.
Bill is driving on his way back to Brown when he gets a call from Bolger. Bolger tells Bill that Brady is dead. His nosy coworker told Bolger how to reach Bill and asks what happened when Bill returns to the office. Bill tells her that Brady was murdered and shot through the heart with a crossbow. Bill tells his coworker that he has to go home and books a flight to Tulsa.
On the flight, Bill meets Ken Fienman (Josh Pais), an orthodontist who is moving back to Tulsa with his family because of his floundering practice. Ken’s wife asks him to leave Bill alone, but Ken is reluctant to do so. At the airport, Ken gives Bill his card and tells him that he never takes accidental encounters for granted. Bolger is waiting outside to pick up Bill and drives him around Tulsa. Bolger takes Bill to a bar in order to get a drink. Bill hesitantly agrees goes with Bolger to the supermarket. Bolger gives Bill one of Brady’s old hats and several people in the supermarket think Bill is Brady and try to beat him up. Bolger pulls a gun and shoots the gun in the air. One of the men kicks Bill in the head and knocks him out.
When Bill wakes up he is being looked after by his brother Brady. Bolger holds Bill down to keep him from beating Brady senseless. Bill is pissed that Brady lied to him and wants to leave. Brady tells Bill that he is getting married and having a baby. Bill remembers babysitting Colleen in high school and just wants to leave. Bill doesn’t interact well with his family because of their drug use. Brady successfully convinces Bill to stay by guilting him into it. Brady takes Bill into the Barn and shows him all the pot. Brady tells Bill how the process works and explains how he makes the most potent weed in the South.
Brady brings Bill onto the back porch and starts smoking. They talk about Heidegger and how philosophers write about the ideas of other philosopher’s ideas. Bill wants to leave but Brady convinces Bill to take a hit. Bill hasn’t smoked a joint since grad school. Bill takes a hit from Bud’s bong and gets very high. They talk more about academia and Brady tells Bill that he got into the business with Rothbaum and that he owes a bit of money. He tells Bill that Bill needs to act as Brady while Brady goes up state to take care of Rothbaum. Two of Brady’s friends visit and Bill, in his impaired state, is taken by Janet (Keri Russell). Brady tells Bill that she is a poet and a catfish catcher. The group has a bit of a party and drinks beer. Bill tells Brady that everything that has happened is the reason why he stays away.
As Brady plays guitar for his guests, Janet and Bill talk to each other. Janet is an English teacher at a local high school to pay the bills and tells Bill that she tried teaching college students but found their minds too closed minded. Bill is clearly taken by her and he tells her that he hasn’t talked to his family in a while. Janet is concerned about Bill’s unconcerned problems with his mother and tells him that without resolving them, he won’t get anywhere. Bill moves in for a kiss but Janet tells him that it isn’t a good idea considering that he’s been smoking and the things she would do to him. Her reciprocation is evident but she tries to leave before anything can happen. She invites Bill to catch catfish in the morning and leaves.
Brady shows Bill his guest room which uses UV light to show the specially decorated room off. Bill insists he won’t stay past the weekend, but Brady doesn’t want to talk about it. Bill goes to sleep and when he wakes up the next morning, Brady has a haircut to match his brother’s. Brady asks if Bill can pose as him but Bill doesn’t want to have a part in it. Brady insists that while he is up in Tulsa, Bill must be here. Brady just wants Bill to visit Daisy, but Bill doesn’t want to see her. Brady wants to trick the sheriff who always sits in front of the old folk home. Bill finally agrees.
Bolger and Brady go up to Tulsa to find Rothbaum. Since it’s Saturday, they realize that they have to find Rothbaum at a synagogue. The two talk about religion and numerous related concepts which man uses to cope as they drive to the synagogue.
Bill is with Janet catching catfish. After Janet catches one and guts it in front of Bill. She asks if he is still leaving in the morning and she tells him she’ll miss him despite the fact that they know each other. She recites a Walt Whitman poem to him, telling him that she understands him and is expressing unbridled passion in a rule-less medium. Bill tells her that a lack of rules doesn’t lead to truth. She tells him that truth is in front of them and what they need is in front of them. The pair kisses and Janet then drives Bill to the old folk home.
Rabbi Zimmerman (Maggie Siff) is giving a sermon in the synagogue. Pug Rothbaum (Richard Dreyfuss) listens intently and notices Brady in the background. Unfortunately, Brady is also noticed by Ken who thinks that Brady is Bill. Brady is confused and doesn’t know who Ken is. Ken watches Brady leave when Pug tells him that they will talk somewhere else.
Bill walks in and says hello to the sheriff. The sheriff takes him to the wall and yells at him since Daisy was caught smoking weed. Despite the fact he can’t prove Daisy got it from Brady, the sheriff is pissed and tells “Brady” that when they find proof they will arrest him and raid his house.
Brady and Bolger talk with Rothbaum at his compound. Rothbaum mocks Brady and Bolger and demands his money back since it’s a year later. Rothbaum explains that the Jews rose to prominence because Christians didn’t want to deal with money and shit jobs, but now they are pissed because the Jews have so much. Rothbaum yells that he wants his money and that if he doesn’t have it, that his dealers will kill them. Before the dealers can react, Bolger shoots both dealers in the head with a revolver. Brady takes out a knife and Rothbaum attempts to fight back with a menorah. Brady stabs and kills Rothbaum and then the two get spray paint and draw inverted swastikas (unknowingly drawing Manji on the walls of Rothbaum’s complex) to make it look like a hate crime.
Daisy is listening to a “bullshit” sermon when Bill sees her. They reminisce about Bill and Brady’s childhood and Bill tells her that he didn’t come down to talk about his childhood fears. She asks why he left, but he doesn’t want to talk about it. She insists and Bill tells her that she was never a mother since she was always doing drugs.
Brandy and Bolger drive to the market in Broken Bow where Bill was beat up and then mess up the people who hurt Bill. Bill, Janet, and Colleen see the news of Rothbaum’s murder. Bill asks Brady what he did and takes him into the kitchen. He yells at Brady and is pissed that Brady did that. He asks why Brady killed Rothbaum and drew a swastika and made it look like a hate crime. Brady tells him that he did it to help his family. Brady asks if Bill will turn him in. Bill realizes that he is now an accessory to the murder and attacks Brady. A phone call for Bill interrupts the fight. Nathan Levee calls Bill from Harvard Law and tells him that there is going to be an investigation about Bill’s conduct with Anne. Bill insists that the entire situation is absurd. Nathan tells him that considering the situation, the offer for his own curriculum is suspended temporarily. Bill calls Anne and asks what the hell she was doing. Maggie Harman, a professor at Brown, claims she saw the two having sex and since she saw it, it happened.
In Tulsa, Ken is driving with his family and his kids are being ridiculous. His family situation sucks and he is struggling to pay bills. Ken hears about Rothbaum’s murder and puts the whole thing together. He drops his family off at the house and looks up what he can find about Bill Kincaid. He finds his high school yearbook online and sees a picture of Bill and Brady together. Ken gets in the car and drives to a gun store and buys a gun. He then drives down the Bill and Brady’s house in Little Dixie.
The two thugs Bolger and Brady messed up tell the sheriff about how Brady is growing pot in the barn and that they killed Rothbaum. The sheriff is interested in this news. Bill asks Janet to come up to Boston with him. Bill gets ready to leave just as Ken arrives in his van. Brady is concerned and Ken is shocked to see Brady and Bill and openly accuses Brady of killing Rothbaum. Bolger goes for a shotgun but Ken shoots out a car window to scare him. He forces everyone together but Bill tells him that he has a plane to catch. Ken wants to extort Brady and Bill for money and tells them that Brady will get the chair and that Bill will spend his whole life in prison. Ken is still paying off the debt from his insurance on the last practice. Ken breaks down and prepares to go home and Brady tells him that he can’t leave. Ken grabs a shotgun and shoots Brady in the chest. Bill shoots Ken several times in the chest as the police arrive. The sheriff sees Brady dying on the ground holding Bill’s gun and Bill over his brother’s body.
Brady dies, making sure that it looks like he killed Ken. Bill gives his brother’s eulogy at the funeral. He makes it clear that he thought of his brother as “a criminal and colossal fuck up” but that he was responsible for the happiest parts of his life growing up. He explains the regret and difficulty of leaving everything behind. Bolger drives Bill up to Tulsa to see Rabbi Zimmerman. Bolger tells Bill that Brady was in prison when they met and Brady saved Bolger from being killed by thugs with box cutters. Bolger laments that he couldn’t repay the favor. Bill tells her the truth about the Rothbaum incident and tells her that Brady wasn’t a racist and didn’t commit a hate crime. She expresses doubt at Brady not being anti-Semitic. She tells him that we act the way we are because we’re animals and asks what he is supposed to do with that knowledge. She tells him all we can do is prepare since we break the world and prepare it for the next great change.
Bill and Bolger go to visit the thugs that ratted Brady out to the police. Bill wants to sell Brady’s growing system to them. Since Brady never paid Pug, the thugs don’t want to pay Bill. Bill refuses to just give the equipment to the thugs. Bill flips on the thug and calls him a “fucking hick”. Bill turns to walk away and is shot through the chest with a crossbow. Bill screams as he bleeds out and Bolger shoots the hicks until they are dead. Bolger carries Bill to the car and drives him to the nearest hospital. A cop pulls them over but then takes them to the hospital.
Janet comes and visits him immediately and finds out that it will be a long recovery for him. Bolger is told that he saved Bill’s life, repaying his debt to Brady. A few weeks later, Bill is sitting outside of Brady and Colleen’s house while Daisy is taking care of the baby. Janet and Bill are sitting drinking lemonade as a summer storm rolls in. It starts raining and the two hold hands over a copy of Walt Whitman’s Leaves of Grass.
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