- Acting in the Dark: To aid her performance as the oblivious wife, Winona Ryder removed all the pages of the screenplay that didn't involve her.
- Cast the Runner-Up: James Franco was originally cast as Robert Pronge before being cast as Marty Freeman.
- The Other Marty: Before production began, director Ariel Vromen shot a test scene with Michael Shannon as Richard Kuklinski and Michael Wincott as Robert Pronge. Shannon kept his role in the feature version, while Chris Evans was cast as Robert Pronge because Vromen wanted someone younger for that part. The director offered Wincott another role but he wasn't happy with it and amicably refused.
- Playing Against Type: David Schwimmer shows up as trigger happy gangster Josh Rosenthal. Same goes for Chris Evans as Mr Freezy.
- What Could Have Been:
Trivia / The Iceman