Road to Perdition

Michael Sullivan, Sr. (Tom Hanks) is an enforcer for Rock Island Irish mob boss John Rooney (Paul Newman), during the Great Depression. Rooney raised the orphan Sullivan and loves him more than his own biological son, the unstable Connor (Daniel Craig).

Connor snaps and kills disgruntled associate Finn McGovern when meeting him with Sullivan, resulting in Sullivan gunning down McGovern's men. Sullivan's twelve-year-old son Michael Sullivan, Jr. (Tyler Hoechlin) had hidden in his father's car and witnesses the event.

Despite Sullivan swearing his son's secrecy and Rooney demanding Connor's apology for the reckless action, the nervous Connor suspects witnesses and acts. He murders Sullivan's wife Annie and younger son Peter, mistaking him for young Michael, while sending Sullivan to his death at a speakeasy. However, Sullivan escapes to Chicago with his son to seek Al Capone, for work and for Connor's location, who is in hiding.

Sullivan is rejected when asking Capone associate Frank Nitti (Stanley Tucci) and Rooney is aware of the meeting. He reluctantly allows Nitti to dispatch crime scene photographer and assassin Harlen Maguire (Jude Law), who likes to photograph his victims, to kill Sullivan.

Maguire tracks him and Michael to a roadside diner but fails to kill Sullivan, who realizes and cripples Maguire's car wheel before escaping. In response Sullivan begins robbing banks that hold Capone and Rooney's laundered money, hoping to trade it for Connor, while teaching Michael to drive as the getaway. He is impeded when the account money is withdrawn by the mob and visits Rooney's accountant Alexander Rance at his hotel for information. However, he is set up when Rance stalls him until Maguire enters, but Michael warns his father with the car horn and Rance is killed in the ensuing crossfire. Maguire is injured when a bullet shatters glass on his face and Sullivan escapes with ledgers, but as he flees Maguire shoots him in the arm.

Michael drives his father to a farm where a childless elderly couple helps Sullivan to recover. Sullivan bonds with his son and discovers from the ledgers that Connor has been embezzling from his father for years, using the names of dead gang members. As the Sullivans depart, they gift the couple much of the stolen money. Sullivan then confronts Rooney with the information while he attends Mass. While Rooney already knew about the embezzlement and that it must end with Connor's death, he refuses to be the one to give up his son.

One night, cloaked by darkness and rain, Sullivan dispatches Rooney's entire entourage with his Thompson sub-machine gun and walks up to Rooney himself. Rooney mutters he is glad it is Sullivan while an emotional Sullivan pulls the trigger, killing him. Seeing no further reason to protect Connor, Nitti reveals his location to Sullivan, making him promise that this will end. Sullivan goes to the hotel where Connor is hiding and kills him.

Sullivan then drives Michael to stay at his Aunt Sara's beach house in Perdition, a town on the shore of Lake Michigan. However, he is ambushed and shot by a disfigured Maguire. As Maguire prepares to photograph the dying Sullivan, Michael appears and points a gun but cannot bring himself to fire. Sullivan then draws a gun and kills Maguire, before dying in his son's arms. Mourning his father's death, Michael finds his way back to the elderly farm couple to live with them. He states growing up that his father's only fear was his son would be like him and that if asked whether Sullivan was a good man, he would simply reply he was his father.