Donald Fagen and Walter Becker, of the popular 70's band "Steely Dan", addressed a humorous letter to Owen Wilson's brother, Luke, on their blog with claims that the idea of "You, Me and Dupree" was stolen from their song, "Cousin Dupree". (Lyrics to "Cousin Dupree" can also be found on their website.) Only the name Dupree, and the possibility that Cousin Dupree and that Wilson's character Dupree both may have slept on a couch seem to be the only common links in their claims. Owen Wilson replied to this fact saying "I have never heard the song 'Cousin Dupree' and I don't even know who this gentleman, Mr. Steely Dan, is. I hope this helps to clear things up and I can get back to concentrating on my new movie, "HEY 19" (which is the title of a Steely Dan song).
The white haired man at the end of the film, during Dupree's motivational ceremony named Joe, is Owen Wilson's uncle, who also appeared in Wedding Crashers (2005) during the wedding montage scene during Owen's "Jabroni" joke. Wilson confirms the relation in the audio commentary on the DVD of Wedding Crashers (2005).
Although Mandy is mentioned a number of times, the back of her head is seen only for a moment. Her face never actually appears on screen. She is not even in the credits.
Despite getting sixth billing in the credits, Amanda Detmer, who plays Neil(Seth Rogen)'s wife, is briefly seen in the background in a couple of scenes, and has very few lines of dialogue in the movie.
Lance Armstrong: Who is Dupree's inspiration, makes three cameos in the movie. First, he is seen in the biking video, to which Dupree exercises (despite appearances, this is not stock footage, but filmed specifically for this movie). Second, he appears in the dream sequence, where Carl imagines Dupree and Molly on Bob's boat (Armstrong is wearing Dupree's "Say Hello to my little friend" gnome shirt). Finally, in a brief after-the-credits scene, he is shown reading Dupree's book, in exactly the same way that Dupree was seen earlier reading Armstrong's book.
Harry Dean Stanton: (uncredited) as Curly, the man in the bar who is continually complaining about the cot.
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