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 song by The Who. Baumbach borrowed the story because it felt so much like something that could've come from his childhood.
Noah Baumbach originally wanted Wes Anderson to direct. Anderson convinced Baumbach to direct it himself because the film is very personal to Baumbach.
Bill Murray was set to play the character Bernard. He backed out in the last minute because he wanted to take a break after filming Broken Flowers (2005). John Turturro was also considered for the part.
Anna Paquin, who plays Jeff Daniels's love interest, played his daughter nine years earlier in Amy und die Wildgänse (1996) (in which Paquin's character hatches a nest full of abandoned goose eggs and then teaches the resulting baby geese to fly). Jeff Daniels said that it made filming a bit awkward for both of them. In one interview, when asked how he and Paquin got through filming their intimate scenes, he said "we tried not to think about...you know, geese."