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-->IMDB Commenter: "Even when Dupree almost burns the couple's house down having an unauthorized party when the newlyweds are away, the premise seems to be that we are supposed to feel sorry for this lowlife. There just wasn't anything funny or fun about Dupree. His only asset seems being able to annoy."
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* FunnyAneurysmMoment: Dupree idolizes Lance Armstrong. This was before his steroid scandal came out.
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* FunnyAneurysmMoment: HarsherInHindsight: Dupree idolizes Lance Armstrong. This was before his steroid scandal came out.
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* FamilyUnfriendlyAesop: "Even if you work your ass off for your family, it doesn't matter. Nobody will really appreciate your efforts since you're ~not fun enough~ anymore, and your 'free-spirited' friend will be more loved than you ever were."
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* MemeticMutation: The fact that the guys who made this really unpopular movie would go on to make [[Film/AvengersEndgame the most successful movie of all time]].
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* FunnyAneurysmMoment: Dupree idolizes Lance Armstrong. This was before his steroid scandal came out.
* HilariousInHindsight: Carl suspecting Dupree of liking Molly becomes funny when you realize that Kate Hudson and Owen Wilson married after the movie. Of course it's also HarsherInHindsight because they got divorced.
* HilariousInHindsight: Carl suspecting Dupree of liking Molly becomes funny when you realize that Kate Hudson and Owen Wilson married after the movie. Of course it's also HarsherInHindsight because they got divorced.
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* UnintentionallySympathetic: For some, Carl. He works hard to please his father-in-aw and make molly happy, lets Dupree stay at his house, almost nothing works for him... and yet he's the "bad guy" in-story?
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* UnintentionallySympathetic: For some, Carl. He works hard to please his father-in-aw obnoxious father-in-law and make molly Molly happy, lets Dupree stay at his house, almost nothing works for him... and yet he's the "bad guy" in-story?in-story?! Whaaaaaaa...?!
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* AlternateCharacterInterpretation: In his review, RogerEbert criticizes the film for never properly deciding if Dupree is merely an UnluckyEverydude or actually a ManipulativeBastard:
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* AlternateCharacterInterpretation: In his review, RogerEbert Creator/RogerEbert criticizes the film for never properly deciding if Dupree is merely an UnluckyEverydude or actually a ManipulativeBastard:
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* UnintentionallyUnsympathetic: We're supposed to find Dupree hilarious, in a childish and uncouth way. For 90% of the movie, he is... '''not'''.
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* UnintentionallyUnsympathetic: We're supposed to find Dupree hilarious, in a childish and uncouth way. For 90% of the movie, he is... '''not'''.'''not'''.
-->IMDB Commenter: "Even when Dupree almost burns the couple's house down having an unauthorized party when the newlyweds are away, the premise seems to be that we are supposed to feel sorry for this lowlife. There just wasn't anything funny or fun about Dupree. His only asset seems being able to annoy."
-->IMDB Commenter: "Even when Dupree almost burns the couple's house down having an unauthorized party when the newlyweds are away, the premise seems to be that we are supposed to feel sorry for this lowlife. There just wasn't anything funny or fun about Dupree. His only asset seems being able to annoy."
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* FamilyUnfriendlyAesop: "Even if you work your ass off for your family, it doesn't matter. Nobody will really appreciate your efforts since you're ~not fun enough~ anymore, and your 'free-spirited' friend will be more loved than you ever were."
* UnintentionallySympathetic: For some, Carl. He works hard to please his father-in-aw and make molly happy, lets Dupree stay at his house, almost nothing works for him... and yet he's the "bad guy" in-story?
* UnintentionallySympathetic: For some, Carl. He works hard to please his father-in-aw and make molly happy, lets Dupree stay at his house, almost nothing works for him... and yet he's the "bad guy" in-story?
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* AlternateCharacterInterpretation: In his review, RogerEbert criticizes the film for never properly deciding if Dupree is merely an UnluckyEverydude or actually a ManipulativeBastard:
-->"For a while, it's almost like "Film/FatalAttraction" with a blonde best friend instead of an adulterous lover. The movie plays with our sympathies, alternating between revulsion and compassion for Dupree: Is he really a misunderstood guy, down on his luck, who means well but just hasn't grown up and found himself? Or does he have something of the feckless, sociopathic manipulator in him? For a while we're not sure. The problem, in retrospect, is that the movie isn't either."
-->"For a while, it's almost like "Film/FatalAttraction" with a blonde best friend instead of an adulterous lover. The movie plays with our sympathies, alternating between revulsion and compassion for Dupree: Is he really a misunderstood guy, down on his luck, who means well but just hasn't grown up and found himself? Or does he have something of the feckless, sociopathic manipulator in him? For a while we're not sure. The problem, in retrospect, is that the movie isn't either."
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* UnintentionallyUnsympathetic: We're supposed to find Dupree hilarious, in a childish and uncouth way. For 90% of the movie, he is... '''not'''.
