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Don Simpson reportedly hated the film's concept. When he and Jerry Bruckheimer ended their longtime producing partnership, Simpson was happy to relinquish any ties to the film, while Bruckheimer got the green light from BV to begin filming for a summer 1997 release. The film was not affected by Simpson's death in January 1996.
John Malkovich was unhappy during production because the script was being rewritten virtually every day and he had no idea how his character was going to turn out.
The film is dedicated to Phil Swartz, an effects specialist who died during filming, when a rigged plane fell and crushed him. This is actually the second Jerry Bruckheimer production where there was a plane related death on set. Eleven years earlier, Art Scholl, a pilot/cameraman, died during filming of Top Gun (1986) when his camera plane failed to recover from a spin and plunged into the Pacific Ocean.
The Las Vegas scenes were filmed at the legendary Sands Hotel immediately prior to its demolition in late 1996. When the production team heard about the city's intentions to raze the historic landmark, they immediately scheduled a multiple camera setup to take advantage of the rare event, which is what you actually see in the movie.
John Malkovich and Samuel L. Jackson were guests on "The Graham Norton Show" in 2015. Norton had pointed out to them the fact that they had never done a movie together, given their extensive filmographies. Jackson said of Malkovich, "Well, none of my movies are serious, he's a serious actor". Malkovich replied, "No-no, I was in 'Con Air'. If that's serious, I'm an astronaut".