Macaulay Culkin is the world's wealthiest kid, the son of a tycoon worth $70 billion, being raised with anything money can buy, but with only loyal butler Herbert Cadbury as a companion, he lacks any friends his own age. But he thinks he might get his chance when, at a dedication to the reopening of the factory of a company his father, Richard Rich Sr. , recently acquired (intending to modernize the factory and give it away to the workers as a token of goodwill), he encounters a group of sandlot kids playing baseball. Unfortunately, before he is able to talk to them, his too-strict bodyguard, Ferguson , stops him by grabbing Richie's shoulder tightly when he says he wants to play, but Cadbury saves him. warning Ferguson for being too rough with Richie, and says that if he ever does it again, "it will be he who needs protecting."
Unlike most parents of rich kids in movies, Richie's father, Richard, tries to keep in touch with Richie and spend time with his son whenever he can. He even had the Rich family's head scientist, Professor Keenbean (Michael McShane), invent a machine called the "Dadlink" that pinpoints Richard's location in seconds, so Richie can talk to his dad when ever he's away on business. Meanwhile, the greedy CFO of Rich Industries, Laurence Van Dough (John Larroquette), is planning to take the Rich financial fortune, believed to be stored in the Rich family vault that Richard had made vague references to, for his own. With the help of Ferguson, they plot to blow up the plane carrying the Rich family to England by disguising a bomb among the presents that they were to give to Queen Elizabeth II. Cadbury, seeing Richie's loneliness, makes a suggestion to Richie's mother, Regina, and arranges for Richie to stay home with the sandlot kids for a weekend of fun. The weekend allows Richie to earn the friendship of the sandlot kids.
Thanks to the new invention of Professor Keenbean, a machine that translates smell into sound, the bomb is detected, but Richard is unable to get rid of the bomb before it detonates. The bomb destroys part of the wing tips, sending their plane into the ocean. However, both manage to survive on a lifeboat. Believing that the Rich family are dead, Van Dough assumes the head of the Rich corporation, and proceeds to cut the many charitable contributions the Rich family were known for. This includes closing the recently-reopened United Tool factory, which the parents of the sandlot kids relied upon on their living. This angers Richie, who proceeds to the company headquarters and, as a living Rich family member, assumes the leadership position. His business savvy at a young age earns him the deference of most of the company's directors, as well as a good deal of flattering press attention.
Van Dough, however, saw this as a minor setback: as Richie is still underage, his ability to run the business was limited by the powers granted to him by someone who was able to give it to him — namely, Cadbury. Cadbury is framed for the Rich family's murder, and the Rich family's other loyal servants are all fired en masse by Van Dough's edict, effectively isolating Richie from the outside world and making him prisoner within his own home. However, he does get the assistance of Keenbean, who had also been hiding in the Rich house, distrustful of Van Dough and not willing to let his inventions fall into Van Dough's hands. Keenbean overhears Van Dogh and Ferguson plot to have Cadbury murdered and appear to have committed suicide. He manages to sneak Richie out with a plan to break Cadbury escape from prison. After Cadbury gets the supplies, he is attacked by one of van Dough's henchman. Surprisingly, he shows great strength, for his appearance, and knocks the goon unconscious. Cadbury then regroups with his new friends, who are willing to assist Richie in whatever it takes to get his home back.
During this time, Richie was left with the Dadlink. However, Richard's receiver was broken in the crash, and, when Richard manages to fix it, the signal that his father is found is intercepted by Ferguson, who disconnects Richie's modem, leaving Richie (remoting in from a friend's terminal) in the dark as to where his parents may be. Assisted by Keenbean, the kids manage to sneak Richie back into his own house, only to discover that the Dadlink shows that Richie's parents are inside the Rich's house. He is shocked to discover that Van Dough had anticipated his own arrival, and had arranged for his parents' rescue. Held at gunpoint, Van Dough forces the Rich family elders to the Rich vault, while Richie and his friends, who were captured by Ferguson's security, are led to one of Keenbean's machines, intending to kill them. Keenbean thwarts Ferguson's plan, and manages to save the children. Richie then proceeds to take a bag full of Keenbean's inventions in a bid to save his parents.
Van Dough is eventually lead to Mount Richmore, a stone mountain portrait of the Rich family, where the vault is located. There, he is surprised to find that the vault held the Rich family's childhood keepsakes — nothing that was valuable to him. Demanding an explanation, he finds the Rich family keeps their money in banks, the stock market, and real estate because they simply did not value money. Desperate to get the money, he attempts to shoot Richard and Regina, only for Richie to interfere. Van Dough attempts to shoot Richie instead, but manages to barely faze him, his clothes having turned bulletproof thanks to one of Keenbean's inventions. The Rich family then takes the opening caused by Keenbean's invention to escape. The chase eventually leads them down the side of the mountain, where they are under further attack by Ferguson and a special rock-blasting laser that had been used to build the mountain vault. Cadbury finally manages to disarm Ferguson and manages to keep the Rich family safe, while Van Dough hangs on for dear life. Although Richard abhors firing staff, he allows Richie to fire Van Dough, who is then subsequently arrested.
Later, as Richie is playing baseball with his new friends on the Rich mansion's yard (with Cadbury as team coach) and hits a home run, Richard and Regina state that Richie now really is the richest boy in the world as he has found the true treasure in life, the one thing that money can't buy — friends. Cold claws...
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