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Tommy Boy is a 1995 American 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 movies that Peter Segal has filmed with former SNL castmates. The film was shot primarily in Toronto and Los Angeles under the working title "Rocky Road". 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. The film did well commercially, but received mixed reviews from critics. Since its release, Tommy Boy has become a cult classic and been successful on home video.

Plot

After seven years at college, Thomas R. "Tommy" Callahan III (Chris Farley) barely graduates from Marquette University and returns to his hometown of Sandusky, Ohio. His father, industrialist and widower Thomas R. "Big Tom" Callahan, Jr. (Brian Dennehy), 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 (Bo Derek), a woman he had met at a fat farm, and that her son, Paul (Rob Lowe), will become Tommy's new stepbrother. However, 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 his father's sycophantic assistant, Richard Hayden (David Spade), a childhood acquaintance who is annoyed over Tommy's ability to be lazy and yet be rewarded.