- The Cast Showoff: Clint Eastwood did his own piano playing.
- Dawson Casting: Frank is only supposed to be in his early 50's, but Clint Eastwood was 62 at the time of filming. On the other hand this is one example where it would be more believable to have had the character closer to Eastwood's real age at the time. Secret service agents need to be at least 21 at the time of application, and assuming a date of birth of around 1940, Eastwood's character would have been at most 23 when he was part of the Kennedy detail. Not impossibly young, but unusually young for that job. An age of around 25-27 would have been more likely, making the character in his late 50's thirty years later.
- Development Hell: The script was written roughly ten years before the movie finally made it to the big screen.
- No Stunt Double: The 62-year old Clint Eastwood (with the help of a safety belt) actually did hang six stories above the ground on the ledge scene, although stuntmen did the jump and the fall onto the fire escape.
- Saved from Development Hell: Jeff Maguire's script had been knocking around Hollywood for over ten years before it got picked up.
- Throw It In!: John Malkovich improvised the part where Leary bites Frank’s gun.
- Uncredited Role: Steve Railsback as David Coppinger.
- What Could Have Been:
- Robert De Niro was the first actor approached to play Leary, but was busy directing A Bronx Tale. Willem Dafoe, Ed Harris, and Jack Nicholson were also considered. Reportedly, Vincent D'Onofrio was originally cast as Leary before John Malkovich took over.
- Warren Beatty, James Caan, Sean Connery, Gene Hackman, Dustin Hoffman, Tommy Lee Jones, Val Kilmer, Nick Nolte and Robert Redford, were considered for Frank Horrigan.
- Glenn Close and Sharon Stone were considered for Lily Raines.
- Bill Pullman was considered for Al D'Andrea.
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