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.
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.
According to one of the DVD commentaries, Joe Carnahan had Ryan Reynolds wear one of his contacts from The Amityville Horror (2005) in the final scene. The contact was worn on the side of his face, with cuts from the climactic shoot-out.
DIRECTOR CAMEO (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.
The movie features three actors who appeared on Lost (2004): Matthew Fox (Jack Sheppard in "Lost") plays Bill the Security Supervisor, Nestor Carbonell (Richard Alpert in "Lost") plays assassin Pasquale Acosta, and Kevin Durand (Martin Keamy in "Lost") plays Jeeves Tremor.
After getting the call that Israel agreed to the deal, Carruthers tells Messner that Israel agreed to give up his whole "entourage". Jeremy Piven, who played Israel, is probably most notable for portraying Ari Gold on the show Entourage (2004).
The bonus features reveal that Ben Affleck, who plays one of the bondsmen, couldn't play pool to save his life at the time. He appeared to have no experience with a pool cue, and as a result, the simplest of shots took many takes.
Chris Pine replaced Michael Shannon as Darwin Tremor. Both actors would later appear in the DC Extended Universe. Shannon would play General Zod in Man Of Steel (2013) Pine would play Steve Trevor in Wonder Woman (2017).
(At around twenty-six minutes) When Buddy is complaining to Ivy about the hotel suite, he says "f**k this and the f**king animal kingdom" before he gets interrupted by Hugo, played by Joel Edgerton. Joel Edgerton, ironically, starred in the Australian crime drama, Animal Kingdom (2010).
The trivia item below may give away important plot points.
Only one female character is killed throughout the movie, the prostitute accidentally shot in the face by Georgia Sykes (Alicia Keys). Ironically, she had specifically said earlier in the movie, that she didn't want to kill any women. Not unless you count her partner, who gets shot by the feds, just as she notices Georgia is still alive.