Trivia
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Spoilers (1)
In the motel room, on the TV in the background is a preview for Naked Gun 33 1/3: The Final Insult, also directed by Peter Segal.
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When Bo Derek's character comes out of the pool, Tommy says to Big Tom (Brian Dennehy), "Whoa, dad. She's a... ten!" Bo Derek and Brian Dennehy both appeared in 10.
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In the scene where they are at the wedding reception for "Big" Tom Callahan you can see Chris Farley's brother sitting to Chris's left when Big Tom asks Tommy Boy to help him out with the song.
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David Spade refused to let the set's stylist work on his hair. This accounts for his hair's tousled appearance in the film.
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When Paul Barish attempts to sabotage the Callahan delivery trucks, the gun he uses is a Sturm, Ruger Mini 14.
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The bassist in the band that plays at the wedding plays a Fender Precision Bass with a tobacco sunburst finish
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The auto shop garages in one of the Zalinsky TV ads are actually Canadian Tire Corporation auto service centre garages.
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David Spade's character Richard Hayden says that 'Big' Tom, played by Brian Dennehy was like a father to him. Brian Dennehy would go on to play David Spade's father as Red Finch in the TV comedy Just Shoot Me!
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The role of Helen,the waitress was originally to be played by 'Rosanne' but she was busy at the time, and unable to appear in the film.
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On the DVD commentary director Peter Segal reveals that they used James Newton Howard's score to Dave and George Fenton's score to Groundhog Day as temp-track music. The Groundhog Day music was used as temp score in the "airplane scene".
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The lunch box young Tommy is carrying at the beginning of the film while running for the school bus is a Brady Bunch lunch box.
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According to David Spade, he and Chris Farley got into a physical altercation on the set. Spade had gone out for a drink with Rob Lowe the night before. Farley had become very jealous and angrily repeated "How's Rob Lowe?". He stepped on Spade's hand and the fight began. After the fight, Spade walked off the set and refused to continue filming.
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Spoilers
The film is actually an update of Shakespeare's 'Hamlet': Tommy is the Prince, his father dies, his mother (Bo Derek) is Gertrude, in reality married to his "step brother" (Rob Lowe) who is Claudius. David Spade's character is Horatio.
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