- Alternate Character Interpretation: In his review, Roger Ebert criticizes the film for never properly deciding if Dupree is merely an Unlucky Everydude or actually a Manipulative Bastard:"For a while, it's almost like "Fatal Attraction" 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."
- Family-Unfriendly Aesop: "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."
- "Funny Aneurysm" Moment: Dupree idolizes Lance Armstrong. This was before his steroid scandal came out.
- Hilarious in Hindsight: 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 Harsher in Hindsight because they got divorced.
- Memetic Mutation: The fact that the guys who made this really unpopular movie would go on to make the most successful movie of all time.
- Unintentionally Sympathetic: For some, Carl. He works hard to please his obnoxious father-in-law and make Molly happy, lets Dupree stay at his house, almost nothing works for him... and yet he's the "bad guy" in-story?! Whaaaaaaa...?!
- Unintentionally Unsympathetic: We're supposed to find Dupree hilarious, in a childish and uncouth way. For 90% of the movie, he is... 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."
YMMV / You, Me and Dupree