Although the movie is heavily autobiographical, director and writer Noah Baumbach said he never pretended to have written "Hey You" by Pink Floyd for a school contest. In reality, a friend of his did it with a The Who song, and Baumbach borrowed the story because it felt so much like something that could've come from his childhood.
Anna Paquin, who plays a love interest to Jeff Daniels in the film, played his daughter nine years earlier in Fly Away Home (1996) (in which their characters attempt to set a flock of orphaned Canada Geese back on their migratory path). Upon the release of The Squid and the Whale (2005), Jeff Daniels said that this previous experience made the filming a bit awkward for both of them. His comment to one interviewer about how he and Paquin got through the filming of their intimate scenes was, "we tried not to think about...you know, geese."
Sophie's father is played by one of the film's producers, Peter Newman, and her sister, Greta, is played by Greta Kline, younger sister of Owen Kline, who plays Frank. Greta is the girl who sings Mr. Mister's "Kyrie" at the school talent show auditions.
Jeff Daniels' character says that he is going to SUNY Binghamton to do a reading towards the end of the movie. While the film is not actually shot on the campus of Binghamton University, the actor who plays Ivan, William Baldwin, is an actual alum of BU.
The surname of the film's central family is "Berkman." One of Bernard's graduate students is portrayed by artist Bo Berkman, a friend & collaborator of director Noah Baumbach. Many of Bernard's other graduate students are also portrayed by personal friends of Noah Baumbach.
Near the end of the film, Bernard is reading a book that he dismisses as "pulp," but acknowledges "Leonard is the filet of the crime genre." The title is not mentioned, and the front cover is not shown; but based on glimpses of the back cover, it can be seen the book he is reading is LaBrava, written by Elmore Leonard.
The trivia item below may give away important plot points.
Ivan is strikingly similar in appearance and mannerisms to renowned author David Foster Wallace. Bernard's excuse for Joan leaving him throughout the film is that he is not as "successful" a writer as he once was. Though this is never proven in Joan's character and reasoning, her getting together with Ivan is perhaps the only proof Bernard has of this excuse, and why he shows so much physical pain in reaction to it.