While hosting a party in his Manhattan penthouse, financial publisher Chris Thorne (Chevy Chase) meets lawyer Diane Lightson (Demi Moore) and agrees to escort her to consult a client in Atlantic City on the following day. Thorne's clients, obnoxious but wealthy Brazilian siblings Fausto and Renalda Squiriniszu (Taylor Negron and Bertila Damas), meet up with them and invite themselves along.
Chris takes a detour off of the New Jersey Turnpike, ultimately ending up in the run-down village of Valkenvania. After running a stop sign and subsequently attempting to escape pursuing officer Dennis Valkenheiser (John Candy), the group is captured and taken before his 106-year-old grandfather Judge Alvin Valkenheiser (Dan Aykroyd). After Chris offends the judge, the yuppies are locked in a hidden room under the courthouse to be judged the next day, and they overhear the judge violently executing a group of convicted drug dealers in a deadly roller coaster nicknamed "Mr. Bonestripper".
Chris, Diane and the Brazilians attend the judge's dinner, learning that the Judge is holding them there as retribution for a coal deal which the Valkenheiser family blames for their poverty. The group attempts an escape, but Chris and Diane are captured by Alvin's mute granddaughter Eldona (Candy, in a dual role). Meanwhile, being chased by Dennis' trigger-happy cousin, Miss Purdah, the Brazilians escape by cutting a deal with Dennis, who decides to escape with them.
The Judge holds Chris and Diane hostage, but they eventually escape, get lost through hidden hallways and slides and become separated. Diane escapes into the property's salvage yard; here, she meets two man babies named Bobo (played by Aykroyd) and Lil' Debbull (played by John Daveikis), the judge's severely deformed grandchildren and they're not allowed to live in the house and have to live in the salvage yard. Befriending the creatures, Diane notices Eldona destroying Chris's BMW 733i. Chris sneaks into the Judge's personal quarters but is quickly caught. Valkenheiser punishes him per house policy, which decrees that Chris must marry Eldona.
Meanwhile, in the court room, Digital Underground is being held on charges of speeding, but the Judge releases them after being charmed by an impromptu rap performance. He also asks them to stay as witnesses for the wedding, which Chris reluctantly goes through with in exchange for his life, but is later caught pleading the band to help him escape. The band leaves without understanding him, and a furious Alvin sentences Chris to die in "Mr. Bonestripper". The machine breaks down the instant before Chris is fed into it, and he escapes. The Judge nearly kills Diane with another claw contraption known as the Gradertine, but Chris retrieves her at the last second and the two jump on a freight train back to New York.
After the two report their plight to the authorities, the Judge's courthouse is raided by local and state police. Chris and Diane are asked to accompany the officers to the site, only to find out that the officers involved are fully aware of and in league with the Judge. The couple escapes when the area's underground coal fires cause a collapse, destroying the town. Chris and Diane return to New York, but Chris sees the judge on television, brandishing Chris's driver's license, announcing that he and his family plan to move in with his new grandson-in-law in New York causing Chris to comically flee for his life.
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