- Ability over Appearance: Physically, Tom Hanks bears very little resemblance to the protagonist of the graphic novel. After seeing him get into the part, though, you probably won't care.
- Actor-Inspired Element: The moment where Michael puts his Tommy gun together to take on Rooney was at one point the sequence that started the film. This sequence and the moment where Sullivan leaves his sleeping son a goodbye letter were originally reversed, the letter-giving scene coming before he puts his gun together. It was Tom Hanks idea to switch these scenes to how they are now.
- Awesome, Dear Boy: Due to stereotyping issues, Stanley Tucci generally avoided roles in gangster movies. However, the prospect of working with Sam Mendes was enough for him to reconsider his stance.
- The Cast Showoff:
- Deleted Role: Anthony La Pagila filmed a single scene as Al Capone and it was cut out. However, his scene is thrown into TV showings. Interestingly, Alfred Molina was the producers' first choice to play Capone but couldn't due to schedule conflicts with Frida. Tom Sizemore was also considered.
- Fake American: British actors Daniel Craig and Jude Law as Irish Americans Connor Rooney and Harlen Maguire.
- In Memoriam: Post-theatrical release versions include a dedication to cinematographer Conrad L. Hall, who died after the film opened.
- Playing Against Type: Daniel Craig is a whiny Psychopathic Manchild, Jude Law is a sleazy, amoral Professional Killer, and Tom Hanks is a grim, stoic mob enforcer.
- Real-Life Relative: Jennifer Jason Leigh (Annie Sullivan) is the half-sister of Mina Badie, who plays the waitress serving the father and son in the movie.
- Release Date Change: The film was riginally set for a Christmas, award-contention 2001 release until Sam Mendes asked for more time. Instead, it was released in the summer of 2002 in the middle of blockbuster season.
- Self-Adaptation: Max Allan Collins wrote the Novelization of the film which itself is based on his comicbook. He also wanted to write the adapted screenplay but was not given the opportunity.
- Throw It In!: The scene where Rooney slams his hand down on the table in anger was an improvisation from Paul Newman during a read-through. The scene where Rooney beats on Connor came out of rehearsals with Newman wanting to show a moment where the character beats up then embraces his son. That and he also wanted to hug Daniel Craig.
- Tom Hanks Syndrome: One of the notable examples, which stars Hanks as a gangster with a dead wife and kid.
- Wag the Director: Tom Hanks and cinematographer Conrad L. Hall asked Sam Mendes to tone down the violent excesses of the screenplay.
- What Could Have Been:
- This was originally a Steven Spielberg property, though Spielberg never actively pursued it as a definite project due to his full slate.
- The scene where John Rooney and Michael Sullivan are playing the piano together was originally supposed to be an Irish dance sequence shared between the two of them.
- The scene where Michael confronts Rooney at the church originally also featured two bodyguards on either side of the aged gangster. Michael initially had a line of dialogue he said to these men. Sam Mendes decided to make the scene only about the two, central characters, used a much closer shot that only featured Tom Hanks and Paul Newman, and CGed Hanks mouth to make it appear closed instead of delivering the dialogue to the bodyguards.
- In the original screenplay, Rooneys death takes place in a boxing ring in front of thousands of people.
Trivia / Road to Perdition