All the conversations by Agent Carruthers (Ray Liotta) and Agent Messner (Ryan Reynolds) in the surveillance van scene were improvised.
The shot with Ben Affleck in the bar, where he sinks the eight ball, and continues with his monologue, took over twenty shots, mainly because Affleck couldn't make the shot. When he finally did make it, he couldn't say his lines, because he was laughing so hard about finally making it.
After filming their scene together, Ben Affleck remarked to Joe Carnahan about Chris Pine: "If I could take ten percent of what I'm going to make in my career and bet on anybody, I'd bet on that kid".
In a rare speaking event, filmmaker Terrence Malick has stated this film is "very well directed", and became one of his favorite films of all time.
Writer and director Joe Carnahan needed to fill the role of a speed freak neo-Nazi when he fired Michael Shannon for being rude to a costume designer. Within ten seconds of Chris Pine starting his audition, Carnahan was sold.
Joe Carnahan: When Jack Dupree (Ben Affleck) is talking about Buddy Israel (Jeremy Piven), it shows a bank robbery going on. For a split second, you see a man with a beard and sunglasses leaning his back on a truck yelling out, and holding a machine gun. This is Carnahan.