Brutal gangster Dragna recruits professional killer Jack to pick up a bag and wait for his arrival at a motel. Dragna stresses that Jack is not to open the bag or allow anyone to view its contents under any circumstances. Confused as to why Dragna wants him to do such an apparently easy job, Jack presses for more details, but Dragna only reiterates the rules. While Jack acquires the bag, Dragna's henchman shoots him in the hand, and Jack stuffs the body in his car's trunk. Dragna is unsympathetic when Jack calls him and instructs Jack to stick to the plan.
At the motel, Jack meets several people: Ned, the wheelchair-bound desk clerk; Rivka, a tall hooker; and Lizard and Guano, a pair of pimps. Jack requests room number thirteen, and Ned cautions him that it is a deathtrap, as it is unconnected. When two suited men become curious about Jack, he abruptly breaks into their room and kills both. A subsequent search reveals FBI badges and a briefcase. Jack sets the briefcase aside and leaves to dump the corpse stored in his car. He returns once he is spotted, only to discover that Rivka has broken into his room; fearful that Lizard will kill her, she requests that he allow her to stay.
Jack initially demands that she leave, then detains her when he cannot be sure whether she opened the bag. Rivka points out that the briefcase contains a photo of the bag, and Jack becomes worried that others may attempt to acquire it. When Jack attempts to drive Rivka to a bus station, she spots the corpse in the back of his car. Lizard and Guano first question Jack about Rivka; later, on the road, they attack him. On their corpses he finds another photo of the bag; unsure what to do with Rivka, or of her involvement, he returns to the hotel with her to await Dragna's arrival.
Ned becomes suspicious that Jack has a guest in his room, and he calls the sheriff when Jack refuses to pay the double occupancy fee. Sheriff Larson briefly questions Jack, and, after Larson leaves, Jack threatens Ned. Increasingly worried about the safety of the bag, Jack buries it near the motel, only to be caught by Ned, who is now out of his wheelchair. Jack kills Ned and returns to the motel, where Larson arrests him under suspicion of Ned's disappearance.
As Larson prepares to torture Jack for information, Rivka shows up. Larson threatens to rape her, but she overpowers a deputy and frees Jack, who then kills Larson. When Rivka demonstrates detailed knowledge of the bag, Jack becomes suspicious of her again, but she points out that she has saved his life. Somewhat mollified, he retrieves the bag and waits in room fourteen. Dragna finally appears, disappointed in Jack's apparent lack of trust. Nonetheless satisfied that Jack has not looked in the bag, Dragna explains that the whole situation was a test of Jack's skills and character, as he doubted Jack's resolve in the wake of Jack's fiancee's unsolved murder some months earlier. The motel and the local cops are all on Dragna's payroll, and were all (unwittingly) part of the test.
As Dragna prepares to leave, Rivka spontaneously tells Jack that she looked in the bag. Frustrated, Jack points out that Dragna will now kill them both. Jack dutifully reports Rivka's action to Dragna, who orders her killed. Jack instead kills Dragna's bodyguard, who wounds Rivka. Jack hunts down Dragna, and both are wounded. Jack looks in the bag; it contains the head of his fiancee, whom Dragna had killed in order to prevent Jack from quitting the murder-for-hire business. Trying to persuade Jack to surrender, Dragna destroys the hotel (where Rivka supposedly is) with remote-detonated explosives. Moments later, Rivka appears and saves Jack by killing Dragna, but she is shot again. Later, in Dragna's lawyer's office, Rivka reveals herself as Dragna's mistress and personal assassin who was sent to the motel to ensure things went Dragna's way. She collects a five million dollar reward for Jack's assassination, and she and Jack drive off together.John Cusack as Jack
Rebecca Da Costa as Rivka
Robert De Niro as Dragna
Crispin Glover as Ned
Dominic Purcell as Larson
Sticky Fingaz as Lizard
Martin Klebba as Guano
Theodus Crane as Goose
David Shumbris as Pike
Mike Mayhall as Deputy Jones
Danny Cosmo as Bishop
David Grovic as Dragna's lawyer
Rotten Tomatoes, a review aggregator, reports that 10% of 42 surveyed critics gave the film a positive review; the average rating was 3.4/10. Metacritic rated it 28/100 based on 18 reviews. Scott Foundas of Variety called it "a tedious, self-consciously quirky postmodern noir". Stephen Farber of The Hollywood Reporter wrote, "If it weren't for the touches of cruelty, this might have been a passable B-movie, but Bag Man ends up wasting the A-list talent caught up in the lurid exercise." Stephen Holden of The New York Times described the plot as "a protracted and increasingly tedious cat-and-mouse game" that "pathetically tries to build up expectations about what might be in the bag". Mike D'Angelo of The A.V. Club called it a Quentin Tarantino knock-off made two decades too late.