Cinematographer Sven Nykvist had lost much of his sight at the time of filming. Allen would describe the scenes to Nykvist so Nykvist could tell Allen how each scene should look. This partially became the basis of Allen's blind director in Hollywood Ending (2002).
Charlize Theron - who had been a model before becoming an actress - had publicly vowed never to play a model on-screen. Woody Allen was aware of this, and wrote her a letter specifically asking her to change her mind about that, so that she could appear in his film.
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.
According to Allison Janney, neither she nor Allen knew the proper pronunciation of the word "triplex". After she did two takes pronouncing it as "try-plex", Allen told her to find the right pronunciation. She decided to ask real estate magnate Donald J. Trump, who was on the set preparing for his cameo. Trump told her it was "trip-lex", and that is how she pronounces it in the film.
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.
Joe Mantegna's character Tony Gardella asks his family, "What am I, Don Corleone?" Mantegna played Joey Zasa in The Godfather: Part III (1990), while Allen's longtime collaborator Diane Keaton played Kay Adams-Corleone in the Godfather trilogy.