Paul Peterson, vice president of Schyumer Corporate Enterprises enjoys making love to several of his female colleagues and firing anyone that he sees fit, despite not being the actual leader of the company. However, one day, after firing his file clerk, Carly, Paul finds himself at the hands of a sinister train one evening that he curiously boards, oblivious to its true destination. After a frightening encounter with the train's passengers, Paul finds himself back in his bed, no worse for wear, with seemingly only one connection to his "dream", a mark on his hand, branded in the shape of an eye. Paul goes to work, attempting to resume some normalcy only to find himself seduced by one of his subordinates, Maddie, who quickly reveals herself to be a demon, hellbent on putting Paul back on the train. Paul manages to defeat her only to be with another horrifying encounter, this time, a demon, hiding inside a computer virus that tries to take Paul to hell by pulling him through the computer. Luckily, at the last minute, he is saved by Gwendolyn, a mysterious employee of the company who reveals herself to be Paul's Guardian Angel. Paul, not the least bit impressed by her sassy personality, learns that the train stalking him is The Night Train, a tool used by Satan to deliver unclean souls to hell. Gwendolyn informs Paul, he can stop it by changing his ways which Paul quickly ignores as he rushes to a meeting with his best friend Steven. At the meeting, Paul ignores Steven's kindness and is soon inundated with a swarm of botflies that attack Steven. The flies chase Steven out of the restaurant where he is hit by a car and subsequently dies. Paul, quickly realizing the error of his ways, complains to Gwendolyn who quickly reminds Paul of better times by showing him glimpses of his past through flashbacks. In them, Paul reveals his strong re-desire to connect with his ex-wife and former lover Janet who funnily enough, works under Paul at the same company. Paul decides to re-connect with Janet as he suddenly finds himself at the hands of another demon, this time, his tech-support guy Charlie, who enjoys mocking Paul's mistakes in life and tries, like Maddie, to put him back on the train. Paul is saved once again by Gwen and eventually meets up with Janet where she ends up forgiving him. Their reunion is interrupted by Charlie who tries to kill Janet but is saved by Gwendolyn. Paul and Janet escape back to the office where they are confronted by Scott Schyumer, Paul's boss, who, after firing most of his staff in the most sadistic ways possible, offers Paul his position. Paul declines, to Scott's disappointment, and quickly reveals himself to be the Conductor of the train, the mastermind behind it all. He attacks Paul, along with Maddie and Charlie and the four (along with Janet and Gwendolyn) engage in an all-battle, to the tune of Funny Girl. Gwendolyn and Paul manage to kill all three demons and defeat the Night Train. As the company shuts down, and Paul and Janet leave for a much needed vacation, a mysterious figure assigns Gwendolyn another task, one that she never saw coming.