According to writer and director Mike White, his father worked as a minister and, at times, questioned his own success. White made the film partially to thank him and to show that he considered him very successful.
Ben Stiller became interested in the film after being moved by the script's portrayal of the father-son relationship between Brad and Troy.
Many of the scenes set in Boston, Massachusetts were filmed in Montreal, Quebec, Canada.
Luke Wilson, who plays Brad's college friend Jason Hatfield, was originally the top choice to play Billy Wearslter, a role that went to Jemaine Clement.
Xavier Grobet, the Director of Photography and cinematographer for this film, also plays the husband of Nick Pascale, Mike White's character.
Mike White: The writer and director plays Nick Piscale, one of Brad's college friends who, fittingly, becomes a successful filmmaker.