Tommy Boy is a 1995 American buddy adventure comedy film directed by Peter Segal, written by Bonnie and Terry Turner, produced by Lorne Michaels, and starring former Saturday Night Live castmates and close friends Chris Farley and David Spade. This was the first of many films that Segal has filmed with former SNL castmates. It tells the story of a socially and emotionally immature man (Farley) who learns lessons about friendship and self-worth, following the sudden death of his industrialist father.

Plot

After seven years at college, Thomas R. "Tommy" Callahan III barely graduates from Marquette University and returns to his hometown of Sandusky, Ohio. His father, industrialist and widower Thomas R. "Big Tom" Callahan Jr., gives him an executive job at the family's auto parts plant, Callahan Auto. In addition to the new job and office, Big Tom reveals that he plans to marry Beverly Barrish-Burns, a woman he had met at a fat farm, and that her son, Paul, will become Tommy's new stepbrother. However the day of the wedding, while the party Big Tom dies from a sudden heart attack during the wedding reception. After the funeral, doubting the future of the company without Big Tom, the bank reneges on promises of a loan for a new brake pad division and seeks immediate payment of Callahan Auto's debts. Tommy suggests a deal: he will let the bank hold his few inherited shares and house in exchange for the bank giving time to sell enough brake pads to prove the new division's viability. If enough brake pads are sold by the deadline, the bank will grant the loan. Tommy then sets out on a cross-country sales trip with Big Tom's scornful assistant, Richard Hayden, a childhood acquaintance who is not only annoyed over Tommy's immaturity and poor work ethic, but believes it was he, Richard, who should have replaced Big Tom as corporate head.