Michael Woods (Joey Lawrence) is a young, preppy twenty year old with a lazy work ethic living off of the wealth of his parents in Los Angeles, California, limping his way through college and dating a spoiled heiress named Gina (Jolie Jenkins), whom his family dislikes. He learns that his younger cousin Tommy Biggs (Andrew Lawrence) will soon be arriving in Los Angeles to visit, the two having not seen each other in several years.
From the moment of his arrival until his departure, Michael casts Tommy aside, prioritizing his social life and the demands of his girlfriend over his guest. Believing it would be sufficient to entertain Tommy with his family's enormous television and movie library, Michael neglects Tommy for the entire week that he stays. On Tommy's last day, the family housekeeper Arlene informs Michael of his mistreatment of Tommy and will inform his parents about it. Michael responds that he will take Tommy to Disneyland to make up for it. However, en route to the theme park, Michael receives a phone call from Gina pleading for him to meet her at the racetrack so she can introduce him to her father. Michael capitulates and leaves Tommy at a children's daycare center while he runs off to the track.
Michael meets and charms her father over the course of a couple of hours. Then, realizing how late in the day it is, he hurries away from the track to pick up Tommy, colliding with another track patron in the parking lot and sloppily exchanging his information in his hurry. When Michael arrives to pick Tommy up, he learns Arlene had picked him up several hours ago. Michael arrives home to not only face his furious parents and Arlene, but also an outraged Tommy. He informs Michael that, should he ever come to Montana: Tommy will "return the favor".
Shortly after Tommy's return home and during dinner, Michael's mother, Jacy (Leann Hunley), informs him that she had an interesting conversation with both his aunt, Jules (Susan Walters), and Arlene. She confronts him for the way he mistreated Tommy and demands for answers in why he didn't keep his promise and take Tommy to Disneyland. Michael tried to explain that if he told Gina that he had plans to take Tommy for a Disneyland trip, she would've dumped him. Glenn refuses to hear any of it and tells him off that his behavior is disgraceful in choosing his social life and Gina over family. Before he could continue disciplining him, the police arrive at the Woods' household looking for Michael, informing his parents that Deidre White (Channing Chase), the woman whom Michael had been involved in an accident. Though Michael claimed it was a hit-and-run accident, the police reveal that even though both smart enough to get each other's insurance information, White was able to get his plate numbers before Michael left the scene of the accident at the racetrack. Further outraged by his lack of conscience, the Woods determine that the appropriate disciplinary action would be to send him to work on his aunt's ranch in Montana for a month. If his parents get a call from Tommy or his mother, his trip to the French Riviera is cancelled.
Michael arrives in Montana dressed in expensive Italian leather boots, clothing and a brand new cowboy hat, believing it was appropriate attire for the location. His aunt Jules picks him up and takes him home to their ranch where he meets her ranch hands Twister (M.C. Gainey) and Mule (Steve Reevis), as well as a smug Tommy.
Michael is put to work first-thing the next morning, though every task he is assigned by Tommy is deliberately sabotaged. He is instructed to relocate a pile of manure and does so using a shovel and wheelbarrow only to discover after the task is completed that there was a tractor parked behind the barn that would have greatly reduced the amount of time needed to complete the task. Later he is asked to load a large pile of lumber on to a truck, which he completes after a couple of hours only to have Mule say that pickup truck has not been used in years, and a more modern truck is seen nearby. Following a few other mishaps, including being bucked from a bronco, Michael's anger and frustration comes to a head and confronts Tommy. Tommy tells him he got what he deserved, after his repeated broken promises in choosing Gina over him. Michael refuses to play his game and tells him off that his behavior was unacceptable. He admits he only faked getting along with Tommy so he could remain in his parents' good graces and that he doesn't care if his father cancels the French Riviera trip anymore. All Michael wants from him is to get through the next month without being sabotaged. Tommy agrees to play fair from now on, but runs off upset under the impression Michael hates him.
The next morning, Twister overhears what happened and reprimands Michael for his behavior, saying he has a four-year child who works harder than Michael. It was also understandable why Tommy behaved the way he did: after what Michael put him through back in LA, although he agrees two wrongs do not make a right in Tommy's attitude. Twister lets Michael know what he really thinks of him: a selfish, spoiled brat who doesn't care that the Biggs are going through financial trouble and acted like he was entitled to everything by putting himself over his family. Michael is shocked by this news, and Twister expresses surprise, considering he would not have cared to begin with. He implores Michael to change his behavior before it's too late.
After being left alone to rebuild the fence outlining the Biggs' property, Michael slowly adapts and comes to understand the ranch lifestyle and the inherent value it possesses. His relationship with Tommy mends after they bond watching a group of wild horses roam freely on the bluffs nearby. Tommy reveals his father was terminally ill, and his medical bills combined with the loss of labor from his death snowballed into financial woes. Later, Michael learns from Jules that the ranch is going to be foreclosed soon. They're behind on their mortgage and the bank will not allow them any more time. The ranch simply hasn't been profitable enough and that the bank will be auctioning off the ranch and their personal property at the end of the month. Michael is devastated to hear this and sympathizes with Tommy and Jules over their plight. After Michael finished his work, he also apologized to Tommy for breaking his promises for the entire trip while he was in LA and next time when Tommy comes, he will come first from now on. He tries proposing a financial sharing idea, but Twister (now more attentive to Michael given his improved attitude) says that sounds too much like a pyramid scheme, and many people in Montana lack a surplus income to risk on gambling.
Nevertheless, he returns to Los Angeles after a month of service on the ranch, but with a noticeable change of heart. The creature comforts of his city life no longer appeal to Michael, subsequently rejecting his posh lifestyle and finally sees Gina for the person she truly is inside: a needy, spoiled brat (like he was once before his trip to Montana). On a trip to the race track, Michael sees a horse hesitating and throws her rider off. Only after calming the horse down with a trick he learned from Twister, Gina rudely reprimands Michael. However, he refuses to listen and ends his relationship with Gina. At home, Michael chastises his father for not helping the Biggs, only to find Glenn's true reasons behind it. He learns that Glenn offered to bail them out, but Jules was too prideful and refused to accept it. Michael resolves to do something about the Biggs' ranch, and sells his Porsche Boxster to a local dealer to provide a lump sum of cash to allow the ranch to survive a little longer.
Upon returning to Montana, Michael presents the cash to Jules in hopes that she'll fight the bank and try to keep the ranch. Jules, defeated, graciously rejects Michael's offer and suggests that perhaps it's time for she and Tommy to move on. Michael tells her that she shouldn't give up yet because he will try to help her no matter what.
On the day of the auction, the Biggs' possessions are systematically sold off to other locals. Meanwhile, Michael recalls one of the real estate classes he had previously taken in school but performed poorly in. While his paper received a low grade, he recalled the premise was in reference to a land trust which, if arranged in conjunction with the bank, would allow the Biggs to remain on the property indefinitely and continue to work the land without concern over the debt they owed to the bank. Michael rushes into town to negotiate the terms with the bank before everything is auctioned off and, successful, returns to the ranch. He presents his good news, which Jules, Tommy, Twister, and Mule are all stunned to learn. Michael's only condition is that they let him stay on to continue working with the ranch and spend more time with the family. Jules informs him that he can stay as long as he would like. As the auction is canceled, all of their belongings are returned to their home and Michael settles in with his new surroundings. The movie ends with Tommy and Michael rebuilding the tree house.
Joseph Lawrence as Michael Woods Andrew Lawrence as Tommy Biggs Susan Walters as Jules Biggs M.C. Gainey as Twister Leann Hunley as Jacy Woods Robin Thomas as Glenn Woods Jolie Jenkins as Gina Steve Reevis as Mule Freda Foh Shen as Arlene Ian Ogilvy as Miles Nancy Renee as Professor Mallory Baynes Channing Chase as Diedre White Mike Trachtenberg as Lou Dan Martin as Officer Holmes Osborne as Mr. Hawthorne Matthew Lawrence as Cowboy in airport
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