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Aimless Vann Siegert (Owen Wilson) takes a bizarre turn in life and becomes a serial killer, tracking down the miserable, the self-destructive and those who otherwise seem willing to die. His first victim is wretched junkie Casper (Sheryl Crow). After disposing of her body, Siegert rents a room from turbulent couple Jane and Doug Durwin (Mercedes Ruehl, Brian Cox). From there, Siegert plots his murders, gets work at the post office and falls deeper and deeper into a psychotic haze.