Tom Stansfield (Ashton Kutcher) is a researcher at a publishing company who works under the tyrannical Jack Taylor (Terence Stamp). Tom wants to be in creative, but Jack doesn't know anything about Tom's skills. Paul (Jon Abrahams) is Tom's only friend at work. Tom has a reputation for being calm and composed all the time. Nobody has ever seen him angry. Jack calls Tom for a meeting and ends up firing his secretary Audrey, when Tom makes a comment about the coffee. Jack calls Audrey into his office, calls her retarded and fires her after Tom says something about a company being only as strong as its weakest link. Now Tom was only making polite conversations, but Jack makes it look to Audrey that Tom is responsible for her termination of employment.Tom has a crush on his boss' daughter, Lisa Taylor (Tara Reid), who is completely controlled by her overprotective father. She reveals to Tom that her father is making her house-sit for his bird on the same night as a party she wants to attend, but Tom convinces her to stand up to her father and attend the party anyway. Jack is going out of town for a few days on business.Lisa asks him to come to their house that night, leading Tom to think that she has invited him to the party; in reality, she just wants him to fill in for her - he reluctantly agrees. By the time Tom arrives, Lisa has already left, and he meets Jack. Jack gives Tom instructions on how to take care of his pet Owl OJ. It has to be given water, its medications (one of which is inserted into its rectum). Tom has to wear protective covers over his shoes all the time.A comedy of errors ensues, including the return of Lisa's older brother, Red (Andy Richter), on the run from drug dealers. He enters the house on the pretext of looking for an extra copy of the TV guide. Red dumps drugs into the toilet, and instead returns a bag of flour to the drug dealer via Tom.One of Tom's tasks is to guard their owl, O-J, which lives in an open cage (it has not been able to fly due to a deep depression, from the loss of a prior mate). When the bird drinks from the toilet polluted with drugs, it flies away. Tom goes looking for the owl and runs into Old man neighbor (Patrick Crenshaw) who believes that Tom is on his property to ogle at his young wife Sheryl (Angela Little). Tom disarms the old man, who offers to give Tom the piece of Evander Holyfield's ear that Mike Tyson bit off during the boxing match.Jack Taylor's ex-secretary Audrey (Molly Shannon) goes to the house to try to earn her job back. After fighting with her boyfriend Spike (Tyler Labine) who was in the car waiting for her, she stays over at the house. Meanwhile, nobody is wearing shoe covers in the house. Audrey opens a beer using the kitchen counter as leverage and ends up damaging it. Audrey invites her friends to look for the owl including Tina (Carmen Electra) and Speed (David Koechner). Audrey's friends proceed to rob the house of all the silverware.Lisa returns home after finding out that her boyfriend Hans (Kenan Thompson) is cheating on her. Tom hides from her everything that happened, and she spends some time with him thinking he is homosexual. Lisa had earlier seen a gay magazine in Tom's briefcase, but she didn't know that it was not Tom's briefcase. He found it on the subway. He clarifies to her that he's a heterosexual and she starts to like him. Lisa tells Tom that there is a restraining order against Red and he is not allowed within 100 yards of the house.Hans comes by and wants to apologize to Lisa. Hans admits to having cheated on Lisa. Tom tells Hans to move on from Lisa. Tom finds OJ flying outside the house and follows it to a nearby house. Tom is let in by Ken (Jeffrey Tambor), who was waiting for a guy named Albert, who is supposed to be a blind date for his daughter Julie. Julie has recently been in an accident, and very conscious about her looks. When Julie comes down, she is looking hideous, and Tom clarifies that he is not Albert. Of course, Ken believes that Albert is acting that way as Julie is not pretty enough for him and throws him out of the house.Audrey's friend Tina thinks she has breast cancer and asks Tom to feel her breasts. Lisa walks in on them and is disgusted by the situation.T.J. (Michael Madsen), the drug dealer, finds out about the fake drugs and threatens to kill Tom if he doesn't return him his money $20,000. T.J. tries to open a safe and steal the money. However, Tom gives him sleeping pills mixed with alcohol which sends him into a coma. Julie comes by the house and tells Tom that he was telling the truth since Albert came by her place a little later. Julie was bleeding from the back of her, and proceeds to smear everything with blood, wherever she rested her head. Red is attracted to Julie.Because they think T.J. is dead, Audrey and her friends bury him. Later, T.J. escapes from the grave and threatens to kill Lisa. With Red's help, Tom rescues Lisa and she falls in love with him. He then goes to get her father, but on the way back the owl gets into the car making Tom lose control of the car and crash into the house.They find police officers in the house looking for T.J., who ends up getting arrested. Tom believed that it was Jack dealing drugs out of his house and reports him to the police. But then Red says that he is the one who was dealing in drugs, and that his full name if Jack Taylor Jr. TJ was at the house looking for Red, and Red simply used Tom to avoid TJ.Jack Taylor is enraged by the damages done to the house and throws Tom out. Jack orders that Lisa will accompany him to Thailand. The next day, Jack Taylor hears his son Red explaining to Lisa how she should stand up to their father and goes back to Tom. Jack realizes his mistakes and gives Tom a promotion to handle the creative department at the office. Hans goes with Jack to Thailand.Hans turned around the company's factory in Thailand. Audrey found a job at a coffee shop. Lisa restructured the entire company from top to bottom. OJ now drinks only beer.