A striking canary yellow vintage Super Bee halts abruptly on a bustling New York City street as Monty Brogan (Edward Norton) steps out alongside his friend Kostya to investigate a dog injured in the road. The dog, a victim of a brutal dogfight, is left nearly lifeless, and although Monty initially contemplates putting him out of his misery, he ultimately can’t bring himself to do it. Instead, he makes the compassionate decision to take the suffering animal to a nearby veterinary clinic.
Fast forward to late 2002, and Monty is on the verge of entering a 7-year prison term for drug dealing. Spending what may be his last day of freedom in the park with his loyal dog, Doyle, he reflects on the unavoidable future that awaits him. That evening, he’s set to meet up with his childhood friends, Frank Slaughtery (Barry Pepper) and Jacob Elinsky (Philip Seymour Hoffman), at a club, along with his girlfriend Naturelle (played by Rosairo Dawson). While Frank enjoys a lucrative career as a trader on Wall Street, Jacob, an introverted high school teacher hailing from privilege, grapples with unrequited feelings for one of his students.
As Monty visits his estranged father, James, a former firefighter and recovering alcoholic who now runs a bar, the tension is palpable. Though Monty's drug profits stabilized the bar, the shame is evident as James succumbs to temptation and sneaks a drink when Monty steps away. Alone, Monty confronts himself in the bathroom mirror, raging in his mind against the various archetypes of New York life, from cab drivers and firefighters to corner grocers and mobsters, channeling his deep-seated resentment.
Monty’s entanglement with the drug scene ties back to Uncle Nikolai, a ruthless Russian mobster, and Kostya, who implies that Naturelle could have betrayed him, given her knowledge of his drug stash. Although Monty declined to testify against Nikolai, uncertainty looms over what retaliation he may face at the club that night. Memories of his youthful romance with Naturelle cascade through his mind, reminding him of their happier days before his arrest. Desperate for clarification, he persuades Frank to help him uncover the truth about Naturelle's loyalty.
Upon their reunion at the club, Jacob is startled to spot his student, Mary, and Monty extends an invitation for her to join their group. Conversations abound regarding Monty's dim future post-prison; Frank toyingly suggests they open a bar together, contradicting his earlier statement to Jacob that Monty is deserving of his fate. In a heated exchange, Frank laces into Naturelle, accusing her of living off Monty's illicit gains, yet she confronts him, pointing out that he knew the truth all along.
Meanwhile, Jacob finds the courage to express his feelings for Mary through a shared kiss, but they are both left in a state of shock, leading to a disheartening separation. Later, Monty and Kostya approach Uncle Nikolai, who imparts grim advice on surviving behind bars. In a twist, Nikolai reveals that it was Kostya who ratted Monty out, presenting Monty with a brutal choice—to kill Kostya in exchange for safeguarding his father's bar. Monty adamantly refuses, reminding Nikolai of the trust he placed in Kostya.
After this confrontation, Monty sincerely apologizes to Naturelle for his misplaced suspicions. Understanding he has one final task ahead, he heads to the park with Jacob and Frank, asking Jacob to look after Doyle in his absence. Wrestling with fear over potential assault in prison, Monty boldly requests Frank to physically confront him, thinking that entering with visible scars might offer him protection. Frank flatly refuses this request; however, Monty provokes him until Jacob steps in, leading Monty to unleash his frustration in an emotional brawl with Frank, leaving him bloodied and emotionally distraught.
As Monty finally returns home, a moment of solace with Naturelle is interrupted by the arrival of his father, who is set to drive him to Otisville. During the ride, James suggests they escape and head west, offering Monty a final glimpse of freedom. As the car moves through the streets, Monty's mind floods with faces he's come to cherish; enjoying a fleeting fantasy where he envisions freedom, rekindling his love with Naturelle, building a family, and living a long life. The daydream dissolves, and we find Monty, eyes closed and face marred by bruises, sitting quietly in the passenger seat, acutely aware of what he is about to lose.
