Drew Barrymore read for the role of Kimberly, but lost out to Cameron Diaz when Julia Roberts suggested her for the part instead.
Sarah Jessica Parker was originally offered the role of Julianne Potter, but she was not able to take the role because she was committed to HBO in order to play Carrie Bradshaw on Sex and the City (1998).
Michael (Dermot Mulroney) often calls Julianne (Julia Roberts) by her nickname Jules, which coincidentally is her nickname in real life.
In the movie Rupert Everett's characters name is George, but in the script he was originally called Digger.
Julia Roberts and Dermot Mulroney would collaborate again in August: Osage County (2013) 16 years later.
During the "helium" scene, the song being sung was "Annie's Song" by John Denver. Denver would die in a plane crash a few months after the film's release in 1997.
Cameron Diaz and Rupert Everett starred together in the Shrek (2001) movies, playing Princess Fiona and Prince Charming.
The train station at the end of the film is Union Station in Chicago, and the same stairs from the famous bookkeeper scene in The Untouchables (1987) are clearly shown.
Included among the American Film Institute's 2000 list of the 500 movies nominated for the Top 100 Funniest American Movies.
Cameron Diaz played Abigail Breslin's mother in My Sister's Keeper (2009). Julia Roberts played Breslin's mother in August: Osage County (2013).