When a lazy and spoiled 20 year old named Michael Woods invites his cousin Tommy Biggs to come to his house for the weekend, Tommy is excited that he is going to see his cousin after not seeing him for a while. After arriving at Michael's house, he begins to ignore Tommy throughout the weekend, making him feel unwelcome. On the last day for Tommy to leave, Arlene, the housekeeper, has a talk with Michael about ignoring Tommy, and Michael tells her that he will take Tommy to Disneyland and that they will have a good time. As Michael drives both himself and Tommy to Disneyland, he receives a call from his girlfriend, Gina, who is a drama queen and a snob. Gina asks Michael to come to the local racetrack, where she would introduce him to her father, who he had not met previously. Michael agrees, and drops Tommy off at a nearby Kiddie Zone so that he could go to the racetrack. On the way to pick Tommy up, Michael is involved in a minor car accident and gives the wrong information to the victim, Diedre White. When Michael finally arrives back at the Kiddie Zone to get Tommy, he learns from an employee that Tommy had already been picked up by Arlene. When Michael returns home, he and Tommy get into an argument. Tommy leaves the following morning, stating that if Michael ever comes to Montana, he'd like to "return the favor." Tommy's mother later calls Michael's parents to inform them of how rude Michael was to Tommy during his stay and on the top of that police officers arrive at the Woods house informing them about Michael's car accident earlier that day. Michael's parents then decide to punish him by sending him to his aunt Jules ranch in Montana to work for free for a month. His parents also add that if they hear any negative reports from Jules or Tommy, they won't allow Michael to go on his trip to the French Riviera with Gina.
When Michael arrives at the ranch, Tommy begins to exact his revenge by giving Michael complicated tasks to complete, most of which Tommy seems to know Michael will mess up in some way. Michael is also placed under the supervision of two ranch hands, Twister, a gruff cowboy and Mule, a jovial Native American. After being caught goofing off, Twister gives Michael a dressing down and tell him that the ranch is going to be foreclosed on at the end of the month, and added that no one else shared that information with Michael because it seemed he could have cared less. Given a new respect for Jules and Tommy, Michael tries to find some way in order to save the ranch from foreclosure, as well as Mule and Twister from losing their jobs.
In the end, Michael, having studied the concept of land trusts in college, realizes that since his aunt's ranch cares for wild horses, it's eligible to be overseen by the state government and shielded against repossession. Michael also learns a valuable lesson about loyalty and love, which proves to be one of the central aspects of the movie.