In a dim Chicago bar, Tom and Jerry wait for the go-ahead to cleanly eliminate their target, Stanley. Jerry is eager to finish the job immediately, but Tom holds back, and Stanley tries to keep the mood light with jokes as the clock ticks. When the phone finally rings, the film pivots into a flashback that takes us back ten years to 1984, setting up the tangled history that binds them all.
The flashback opens with a younger [Tom] and a youth named Karl. Karl narrates a brutal assault: a local gangster ripped the nose off Karl’s nephew, a crime that unsettles Tom deeply. Although Tom promises to look into the matter, Karl grows wary and bargains as they enter Tom’s car. The uneasy tension culminates when Tom, sensing betrayal, yanks Karl into a fatal moment, strangling him after an apology. Jerry, who witnesses the act, vomits but insists he’s otherwise fine, a pattern that hints at the murkier lines they walk.
Next, [Tom] embarks on another hit that takes them out of state, with Jerry tagging along. Their mood sours as Jerry becomes surly, and Tom allows him to witness the hit at its site—a cinema. There, they encounter an unnamed man who grows irritated by their loud conversation about a domestic dispute with his girlfriend. The man recounts a story about his fiancée, Vicki Torrance, the star of the low-budget action film he’s watching, whose own mob-related troubles ended in tragedy on the set. The tale moves Jerry, who decides to marry his own girlfriend, while Tom and Jerry rise to leave. In a chilling moment, Tom slits the man’s throat, warning Jerry not to become too emotionally entangled in their victims’ stories.
On their first real kill, the duo trails a target to a Chinese restaurant. Jerry’s nerves show, and he makes a spectacle of himself, prompting Tom to calm him with a reference to Ronald Reagan’s fictionally cold-blooded performance as a hit man in a famous movie. The thought of following in such footsteps steadies Jerry enough to pull off the shot. Later, Tom coolly describes their co-worker, Vic, who supposedly once had an affair with Marilyn Monroe and who allegedly helped orchestrate JFK’s assassination, stirring a mix of superstition and bravado in their dynamic. When the next target arrives, Jerry asks to take the shot himself, but Tom lets him try and watches as Jerry awkwardly shoots the man head-on, leaving with a sense of grim satisfaction.
During a meal with Vic, Vic reveals plans to publish memoirs and seek a film adaptation and talk-show appearances. The trio debates who should portray them on screen and who should play each of them, a conversation that skews toward vanity and legacy. A tense moment erupts when Jerry reveals he is diabetic and pulls out a syringe, abruptly stabbing Vic in a moment of brutal indignity. Tom chastises Jerry for killing Vic in such a manner, arguing they had planned to take him out back after dinner for a cleaner death.
The tension peaks when Jerry’s fear overtakes him during their final hit: he panics and accidentally kills an innocent bystander. He then confesses to unsettling fantasies about killing his own family, even admitting at one point to pointing a loaded pistol at his infant son’s head. Back in the present, the phone rings again and Tom takes the call, delivering the hit on Jerry. After freeing Stanley, Tom discovers that Stanley has his own orders—the man tasked with ending Tom’s life. The film closes on Stanley’s quiet, unsettling question: does Tom know any good jokes?
