Continuity mistake: In the confrontation scene where all of Mary's admirers are forcing her to choose between them, Woogie is sat on the couch with a pile of Mary's shoes. Every time the camera shoots back to him, you will notice that the position of the shoes changes each time. This is also mentioned by the directors on the DVD commentary.
There's Something About Mary (1998)
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Directed by: Peter Farrelly, Bobby Farrelly
Starring: Ben Stiller, Cameron Diaz, Matt Dillon, Lee Evans, Chris Elliott
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More mistakes in There's Something About MaryMore quotes from There's Something About Mary
Trivia: When Mary is golfing and she meets Matt Dillon's character for the first time, the woman that walks by is the director's mother. (00:27:35)
Question: Healy tries to impress Mary by pretending to be an architect, drugging the dog, getting new teeth, liking the same movies, and by saying he works with handicapped children. Why then would he call them "r***rds" and say he keeps one in a cage and puts him on a leash like a dog?! Wouldn't he think this would piss Mary off? I never understood that scene and why he would say this.
Chosen answer: Apparently he didn't consider that - either he's just being an idiot or he's trying to make an extremely ill-considered joke. Either way, that's a character mistake, not a movie mistake.
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Answer: Because he is ignorant and doesn't know anything about disabled people, he actually doesn't realise what he is saying is offensive.