Trivia: In the scene where Nicky goes to heaven and meets his mother, a man walks in and she introduces the man as Chubbs. Chubbs was Adam Sandler's golf instructor in Happy Gilmore.
Trivia: Nicolas Cage actually owned the Ferrari 550 Maranello that he drives in this movie.
Trivia: When Maurice is looking for Trish outside the CD store, you can hear him say, "I'm gonna find your Aaliyah lookin ass." Trish is played by Aaliyah.
Trivia: In the scene where Greg is entering the drug store, listen to the lyrics of the music playing on the speakers - they are very similar to his speech when he says grace in the dinner table scene. Obviously where he got his words from, but not immediately obvious unless you listen for it.
Trivia: When Milos Forman, who plays Father Havel, talks to Edward Norton about faith in the private quarters of the church he tells Norton that he came to America when the Russians invaded Czechoslovakia. He actually did so in real life.
Trivia: When Novalee (played by Natalie Portman) is running out of the Wal-Mart after realizing that Willy Jack has left her, there is a poster above the door from Star Wars Episode 1. The poster is Natalie Portman as Queen Amidala. These posters were supposed to have been removed during filming.
Trivia: When Elliot is on the beach, as the devil walks by with two dogs she refers to them as Dudley and Peter, which is a reference to Dudley Moore and Peter Cook - the stars of the original Bedazzled.
Trivia: When Lisa is mad because she can't meet Roro's family, she angrily storms off and Roro calls "Lisa stop" after her. The little girl who eyes them and then mocks Roro by crying "Lisa stop" and storming off is not supposed to be there. Somehow, she got in the middle of the take and they thought what she did was funny, so they kept it in.
Trivia: The 'stain on our country's history' line as Morgan Freeman used in the scalping scene is the same line as Morgan Freeman used in his role in 'lean on me'.
Trivia: When Rob and Laura are lying in bed listening to Ray aka Ian have sex, Laura is reading a book called Love Thy Neighbor. Later on we learn that Laura indeed did love her upstairs neighbor.
Trivia: The fictional childhood of Nick, growing up in a burlesque club surrounded by beautiful, nearly naked women who adored him, is bizarrely similar to the actual childhood of Alan Alda, who plays the boss character. Alan Alda's father ran a burlesque club, and apparently the strippers and dancers treated the young Alda as a mascot, even keeping him in the changing room as they got dressed. However, as an adult Alda became an activist for feminist causes, rather than the chauvinist effect it had on the fictional Nick.
Trivia: As director Bonnie Hunt says on the DVD commentary, she told Minnie (Grace) to hit David (Bob) really hard in the scene when she slaps him, to get a better reaction. This is why his face looks surprisingly cheerful behind his hand as he holds it to his cheek - he's trying very hard not to laugh, as he wasn't expecting it.
Trivia: The Marquis de Sade, a promiscuous man and a convicted rapist died of syphilis (a sexually-transmitted disease) in 1814.
Trivia: Location filming in Calgary's Mount Royal neighbourhood was disrupted when two bank robbers crashed their getaway car into the set. They hit a fake police van and were soon surrounded by over a dozen men and women in uniform. They surrendered only to find out later that they had surrendered to extras. (The real police showed up soon afterwards.)
Trivia: Although Piper Perabo was able to sing for her character, it was decided that LeAnn Rimes would provide Violet's singing voice, albeit with a deliberate deviation from her natural vocal range. This means that during LeAnn's cameo in the movie, she is effectively duetting with herself.
Trivia: The day John F. Kennedy was assassinated (11/22/63), school was let out early. When Maurey and Sam got to her house, it was 12:05 on the wall clock. When Sam went home, it was 12:25 PM. This makes it appear as though they knew about the assassination before it happened (around 12:30 PM), but Dallas falls under Central Standard Time (CST) and the movie is set in Wyoming, which is Mountain Standard Time (MST) or one hour behind CST. That is, 12 PM in Wyoming would be 1 PM in Dallas, Texas.
Trivia: Robert Patrick plays Matt Damon's father in the movie, even though in real life he's only 12 years older than Damon.