The Coen brothers' draft of the script was originally written in the early 2000s, but the project became stuck in development hell after several directors dropped out. Despite several uncredited rewrites that removed many of their contributions, the Coens were still given sole writing credit.
Hugh Grant, Sandra Bullock, and Sir Ben Kingsley were originally attached to play Harry Deane, P.J. Puznowski, and Lionel Shabandar.
While ostensibly a remake of Gambit (1966), the plot of this version is actually quite different.
The script went through a considerable re-write to solidify the movie's PG-13 rating.
In 2004, Jennifer Aniston was announced as the lead of the movie, alongside Ben Kingsley. Burr Steers and then Bo Welch were attached to direct the film.