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After Harry’s arrest of a gambling kingpin results in a conviction for murder, a group of thugs shoot up Harry’s car and try to kill him. Harry overpowers them and is paired with a new partner, Insp. Al Quan (Evan Kim). Within days of this assignment Harry and Al find themselves working on a mysterious death of a rock star, who was on location filming a movie directed by Peter Swan (Liam Neeson). After one of Swan’s crew is killed in a Chinatown robbery that is foiled by Al & Harry, Al discovers a list of celebrities on the dead man that includes the dead rock star and one Inspector Harry Callahan. They soon discover that this is part of a strange game called the Dead Pool, and it isn’t long before other people on the list turn up dead…and someone starts making attempts on Harry’s life…

Peter Parker (Tobey McGuire) can’t seem to catch any kind of break. Being Spiderman has brought him nothing but problems as far as his personal life is concerned. Not only that, Mary Jane Watson (Kirsten Dunst) is engaged to astronaut John Jameson, and Peter may lose her forever. Things are so bad for him that he is pushed past his breaking point, so he decides that he doesn’t want to be Spiderman anymore, until a freak accident transforms Dr. Otto Octavius into Dr. Octopus, a super-villian with four metal tentacles coming out of him. Peter realizes that only Spiderman can stop him, but of course, problems arise. Mary Jane gets caught in the middle, and Harry Osborn, who still blames Spiderman for the death of his father, Norman Osborn, also the Green Goblin, wants him dead. Spiderman will have to push himself past his limits if he’s going to survive.