The character of the King was originally written as weighing 250 pounds and owning a boxing gym. When Dustin Hoffman read the script and told the filmmakers that he was interested in the story, but not in playing that kind of character, they rewrote the King to make him a nightclub owner instead.
For the scene where The King (Dustin Hoffman) meets Jake (played by Edward Burns) and Lily (Rachel Weisz) for the first time, Hoffman and Burns rehearsed the scene extensively. Weisz wasn't included because director James Foley wanted to have her uncomfortable with how the scene might unfold. So, when Hoffman leans over and grabs her by her breast, Weisz's shocked reaction is completely genuine.
Alice in Chains vocalist William DuVall has a non-speaking, uncredited role as a bar patron in the opening moments of the film. The logo of DuVall's then-band Comes With The Fall also appeared in the movie.
Doug Jung wrote the script to take place in New York, and the studio wanted to shoot in Canada as a stand-in. Director James Foley did go on location scouts to Toronto - having used it to stand in for New York before, on Corruptor - Im Zeichen der Korruption (1999) - but, intensely disliking and feeling constrained by the "runaway" filmmaking process, was inspired while driving around Los Angeles during magic hour one evening to rewrite the movie to take place there instead.