|Directed by||Greg Beeman|
|Music by||Marco Marinangeli|
|Country of origin||United States|
|Running time||92 minutes|
|Distributor||Disney-ABC Domestic Television|
|Original network||Disney Channel|
|Original release||November 20, 1999|
|Followed by||Jumping Ship|
Michael Woods (Joey Lawrence) is a young, preppy twenty-one 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). 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 DVD 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, to which 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 exchanging false 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 an outraged Tommy who informs him that, should Michael ever come to Montana he will "return the favor". Shortly after Tommy's return home, the police arrive at the Woods' household looking for Michael, informing his father that Deidre White, the woman whom Michael had been involved in an accident with was smart enough to take down his plates when he left the scene of the accident at the racetrack. Infuriated, Michael's parents determine that the appropriate disciplinary action would be to send him to work on his aunt's farm in Montana for a month.
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 (Susan Walters) 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 be told it was loaded onto the wrong truck—a truck that hasn't run in years—and that the correct truck was actually much closer to the wood pile. Following a few other mishaps, including being bucked from a bronco, Michael's anger and frustration comes to a head and he tells Tommy off.
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 friendship with his cousin mends after they bond watching a group of wild horses roam freely on the bluffs nearby. 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.
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 him, subsequently rejecting his posh lifestyle and Gina who still lives one. He chastises his father for not helping the Biggs, but his father responds that he offered her any amount of money he needed but they were too proud 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, Tommy 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.
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.
- 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 on airport