Development and writing
A remake of Gambit had been mooted for several years. Producer Mike Lobell saw the original film at its London premiere in 1966, and in 1997, Lobell, who was then working at Universal, was looking for a film to remake; he suggested Gambit and Universal approved it. He initially sent the original script to Aaron Sorkin to rewrite it; however, despite being keen to work on the project, the success of Sports Night and more especially The West Wing meant that he could not commit to completing the rewrite. After Sorkin pulled out, Lobell met British producer Andy Paterson, director Anand Tucker and writer Frank Cottrell Boyce. Boyce produced a script moving the story to Japan, but Lobell did not think it was funny enough and decided to move on. Hearing that Joel and Ethan Coen were looking for some rewrite work between films, Lobell gave them the script and they produced a "radical overhaul", moving the story to the United States. The Coens were told the film was specifically intended for Hugh Grant. Half an hour after submitting their completed script, they were informed that Grant had chosen to pass on it. The project remained in development hell.
Initially, Alexander Payne was in talks to direct it, reuniting with Election star Reese Witherspoon, but was reluctant to work on a script he did not write. Witherspoon was willing to remain on the project, but only if Lobell could get Mike Nichols or Robert Altman to direct. After the success of Gosford Park (2001), Altman was keen to make another film in the United Kingdom, especially as Witherspoon was attached. However, prior to signing on, Altman backed out, feeling that the material was not suitable for him. Nichols was not interested and the project stalled.
In March 2004, Jennifer Aniston was announced as the female lead alongside Ben Kingsley, with Bo Welch directing. After the commercial failure of Welch's 2003 live-action adaptation of Dr. Seuss's The Cat in the Hat, Universal lost faith in the project and put it into turnaround. Outside of the studio system, Lobell moved between different financiers in a bid to get the project moving. One group, Alcon Entertainment, had Gerard Butler lined up as Harry Deane, with Richard LaGravenese directing. LaGravenese wanted a script polish, which took a long time, removing a lot of the work the Coen brothers had done. The project was placed on hold again.
The script was well known around Hollywood, and in 2009, Lobell took a call from Roeg Sutherland at CAA. Sutherland knew of a fledgling production company, Crime Scene Pictures, with equity financing from Southeast Asia, who were looking for a marquee project for their new company and felt that Gambit would fit the bill. In 2010, Doug Liman was reportedly considering directing the film. Although initially reluctant to take the project, Lobell persuaded Michael Hoffman to helm the film. In October 2011, Rolfe Kent signed on to compose the score for the film.
