Desmond in Trouble
Desmond Hume hosts a party in his penthouse in Manhattan attended by wealthy guests, including two characters dubbed "Brazillionaires": Fausto and Renalda. Upon meeting attractive young tenant Diane Lightson, Desmond agrees to escort her to Atlantic City in his vintage BMW 733i on the following day. Fausto and Renalda meet up with them and invite themselves along, much to Desmond's chagrin.
The four proceed to Atlantic City where, along the way, Desmond takes a supposed scenic detour off of the New Jersey Turnpike, ultimately ending up in Valkenvania, a burnt-out city composed of decrepit houses, vent pipes, and hillbillies. Failing to comply with a stop sign and subsequently attempting (yet failing) to escape pursuing officer Dennis Valkenheiser, the group is ambushed by a series of man-made obstacles and taken before 106-year-old Reeve Alvin Valkenheiser, who confiscates their identification cards.
The reeve holds the offenders in his courthouse/funhouse to be judged. They attempt an escape, but due to a series of mishaps, the group splits up. All seems lost for the two Brazillionaires until they cut a deal with Dennis, who decides to quit his job as an officer for the Reeve's twisted reign. At points, Desmond and Diane, still trapped within the house, are in high risk of being shot by Dennis' trigger-happy cousin, Miss Purdah.
The reeve is angered by their actions and imprisons Desmond and Diane in a room from which the pair eventually escapes (again with help from Dennis) and, in time, become separated. Diane makes it out of the house and into the property's salvage yard; here, she meets two troll-like creatures by the names of Bobo and Lil' Debbull, who happen to be the judge's severely deformed grandchildren. Earning the creatures' trust, Diane catches glimpses of Alvin's granddaughter/personal mechanic Eldona destroying Desmond's BMW, and comes to the realization that they may not escape after all.
Meanwhile, Desmond sneaks into the Reeve's personal quarters but is quickly caught. Valkenheiser punishes him according to house policy, which decrees that Desmond must marry Eldona. Now trapped in marriage, Desmond pleads for help from another set of the Reeve's victims, the alternative rap group Digital Underground. Although the group's members are being held on charges of speeding, the Reeve releases them after being charmed by an impromptu performance of one of the group's hits.
The judge and his household have a long-standing grudge against "bankers" (in which category they seem to be able to place everybody with more money than themselves) because of the loss of most of the families' wealth during the Great Depression. The judge's invariable punishment for being a "banker," and for just about everything else, is to be fed via roller coaster into a death machine called "Mr. Bonestripper," and have one's remains shot out onto a large charnel heap. Luckily for Desmond, the machine breaks down the instant before he's fed into it, and he escapes. After retrieving Diane from the scrapyard, the two jump on a train back to New York.
After the two report their plight to the authorities, the Reeve's courthouse is raided by local and state police. Desmond and Diane are asked to accompany the officers to the site, only to find out that the agencies are in league with the Reeve. Once again, the two urbanites are forced to flee, as the Reeve deems that they know too much about goings-on in his jurisdiction. The couple only escapes when the area's underground coal fires cause a collapse, destroying the town.
In closing, the Brazillionaires are shown to have made their way back to South America; Dennis is now their personal head of security and Renalda's lover. Desmond and Diane are shown relaxing in New York. Desmond's relief does not last, however, as he stumbles on a televised news segment covering the ruined town of Valkenvania, in which Valkenheiser, brandishing Desmond's ID, announces that he and his family plan to move in with his new grandson-in-law in New York. Desmond runs out of the apartment through the wall, leaving a cartoon-like hole. The last thing the Desmond yelled was "No you won't!". He then decided to sail the world.