Kevin Franklin (Sinbad) is an inner city Pittsburgh native; raised in an orphanage, he has delusions of grandeur, and talks about getting rich and driving a Porsche one day. Twenty-five years later, he drives a rusted MG Midget and all his ambitions revolve around a series of ill fated get-rich-quick schemes. A handshake loan of $5,000 from the mob grows to $50,000 through interest and penalties, resulting in him trying to skip town at Pittsburgh International Airport. He overhears a conversation between lawyer Gary Young (Hartman) and his children, who are waiting to pick up his childhood friend, Derek Bond, who is now a successful, straight-laced and vegetarian dentist. Upon hearing him say that he hasn't seen Bond in twenty five-years and doesn't know what he looks like, Franklin gives his baseball cap to the real Bond to throw off the two dimwitted mobsters chasing him and poses as Bond to the Youngs, who take him to their posh home in Sewickley.
Although he knows nothing about dentistry, Franklin still manages to convince those around him that he is in fact Derek Bond, and his affable personality makes him popular with Young's otherwise stuffy and rich associates. Young has little time for his children and his wife (Kim Greist) who runs a chain of successful new frozen yogurt businesses, which gradually builds a gap between them, largely due to the demands of his bigoted, arrogant boss (Mason Adams) at the law firm where he works; this leads to Franklin developing a bond with Young's Goth daughter, helping her stand up to her cheating boyfriend, and his young son, who has aspirations of playing pro basketball. Young eventually stands up to his boss with Franklin's support and quits the firm to be with his family. Meanwhile, the mob thugs threaten Franklin's best friend, Larry (Stan Shaw), into revealing his whereabouts, and Franklin asks him to pick him up. After he does so reluctantly, he sparks an argument with him over his lack of appreciation of friendship, causing him to realize that Young has been his friend all along. He returns to the Youngs' house only to find that the mobsters have taken them hostage, and his true identity is revealed when the real Derek Bond finally shows up.
After the mobsters take Franklin away, he manages to escape, losing them in a charity marathon, where he meets up with Young, who graciously decides to help him despite his charade, in return for helping bring his family closer together. Franklin reveals that he has an instant lottery ticket he purchased the previous day for a chance at a $1,000,000 cash prize spin on a Saturday night television show, which he reluctantly gives up to the mobsters in exchange for the forgiveness of his debt.
The film fast forwards to wintertime, Franklin parallel parks a shiny new red Porsche with Larry in tow, in front of the Youngs' house, appearing for a promotional party for his new best-seller book, Handbook for Houseguests, based on his experiences with them. The partygoers gather in front of the television to watch the mobsters spin the wheel for the jackpot. It initially lands on the million dollar jackpot, but then falls and lands on $5,000, much to the mafia don's dismay and Franklin's delight.
During the closing credits, Young and Franklin sing a medley of food based parodies of Christmas songs, as they cook a barbecue in Youngs' backyard outside of a Christmas party.
Some scenes for the movie were shot on location at the Pittsburgh International Airport, Pittsburgh's historic Hill District and South Side, Downtown Pittsburgh, and the Sewickley suburb.
The film received negative reviews. Rotten Tomatoes gives the film a score of 15% based on 17 reviews. Caryn James of The New York Times describes the film as "an inane fish-out-of-water comedy" and says "That Sinbad survives with his dignity and comic reputation intact is amazing" but notes that Phil Hartman is not so lucky.
The film debuted at No. 3. It eventually grossed $26 million in North America. When compared to its $10.5 million budget, it was a modest commercial success.