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)
Ending / spoiler
Directed by: Peter Farrelly, Bobby Farrelly
Starring: Ben Stiller, Cameron Diaz, Matt Dillon, Lee Evans, Chris Elliott
Dom (Chris Elliot) is Woogie and has been stalking Mary (Cameron Diaz). Tucker is no architect and is a pizza delivery guy. Brett is none other than Brett Favre and he didn't say mean things about Mary's brother; Brett asks Mary if they can be together again. Ted (Ben Stiller) gets all sad. Mary picks Ted and they get together. The old man who slept with Magda shoots the guitar player that we see singing that song throughout the movie.
Trivia: The man in the prison with the long hair that stretches his arm out of the bars while Ted is leaving is Cameron Diaz's father.
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.