In the movie, Lee Simon is an alumnus of Glenwood High School. Author Woody Allen's alma mater is Midwood High School (class of 1953) on Glenwood Avenue.
Director Trademark: [Woody Allen] [writer] Lee Simon is a magazine writer.
Allen wanted to hire Kenneth Branagh for the lead role but was unsure whether he could pull off an American accent. As Branagh was filming The Gingerbread Man (1998) at the time, Robert Altman screened most of the film for him, and Branagh got the part.
Only Kenneth Branagh and 'Judy Davis' were privy to the complete script.
Leonardo DiCaprio is onscreen for exactly 10 minutes and 20 seconds.
According to Hugh Grant on "Inside the Actor's Studio", he was originally given the part, but lost it later to 'Kenneth Brannaugh'.
The role of actress/waitress Nola was intended for Drew Barrymore but she had to decline owing to a previous commitment to Ever After (1998).
In the scene where Leonardo DiCaprio and Kenneth Branagh are watching a boxing match, magician David Blaine can be seen sitting behind them. Blaine was on the set visiting DiCaprio that day and they put him in at the last minute.