According to the book "Devil's Candy", Bruce Willis was "was generally disliked by most of the cast and crew [due to his ego]." In one instance, during the filming of a scene in which Willis was with Alan King (the scene in which the character played by King dies), Willis challenged the crew to make the whole scene move along faster, allegedly because it was very hot on the set. Although Willis was called out of the set by Brian De Palma to discuss the incident, this particular scene ended up being considerably shorter and simpler than originally intended.
Steadicam operator Larry McConkey coordinated the complex the near 5-minute opening camera tracking sequence that included a cramped ride in a service elevator. This was McConkey's first of a number of memorable collaborations with Brian De Palma as his steadicam operator.
Steve Martin was the original choice to play Sherman McCoy by original director Mike Nichols. Nichols left the project and was replaced by Brian De Palma who also wanted Martin for the role but the producers disagreed and wanted Tom Hanks cast instead.
When the role of the Judge was still going to be Myron Kovitsky in pre-production, as he was in the novel, Joel Grey was considered. Judge Burton Roberts, who was the original inspiration for the character in the book, also was considered and even had a good audition with Brian De Palma. De Palma balked at casting him because of his inexperience in acting and doing multiple takes of a scene.
Walter Matthau originally was offered the role of the judge but demanded a fee of $1 million, according to Julie Salamon in "The Devil's Candy". The producers balked at meeting his price and signed Alan Arkin instead for a modest $150,000.
Bruce Willis was added to the cast to provide box office clout despite the fact that none of his non-action movies had ever turned a profit. His fee was $5 million, $4 million more than top-billed Tom Hanks.
At the very beginning of the opening tracking shot, as the limousine carrying Bruce Willis enters the basement, director Brian De Palma is the first person seen on screen - as the security guard saying "Now arriving Area A" into a walkie-talkie. He hurries off-screen and is next seen seated on the rear of the golf-cart, behind Bruce Willis and Rita Wilson, still "talking" into his walkie-talkie. When the cart stops, DePalma once again runs off ahead of the actors. It was necessary to put himself into this sequence due to the logistics of directing the lengthy and complicated take, and in order to remain unrecognizable he shaved off his trademark beard.
Michelle Pfeiffer was reportedly the original choice to play the female lead by the studio and director Brian De Palma (who had directed several years before in Scarface (1983)). However she turned the role down.
Tom Hanks was chosen to play the lead as he was considered "likeable" by the producers and would dampen the negativity of the character he would play, Sherman McCoy, thus hopefully improving the movie's commercial chances. The casting of Hanks was widely criticized at the time, according to "The Devil's Candy", as he was considered a light comedian. Though he had recently received an Oscar nomination for Big (1988) he had yet to prove himself as a dramatic actor. Hanks hoped this would be his chance to prove himself in drama, but he would have to wait until Philadelphia (1993) to make his mark as a "serious" actor.
In the opening tracking shot, when Bruce Willis gets in the elevator, Brian De Palma can be seen, dressed up as a waiter. It was technically impossible for the camera crew and the director to stay off camera in that shot, so De Palma chose to do a cameo there. To be unrecognizable, he shaved off his trademark beard.
In the film, Bronx District Attorney and candidate for New York City Mayor Abe Weiss states that he hopes the city's black voters see him as the "first black District Attorney of Bronx County." In fact, in November 1988 (two years before the film was released), Judge Robert T. Johnson was elected the first black district attorney of the Bronx, a position he still holds.
Michael Cristofer's original script ended cynically with the supposed victim of the hit-and-run walking out of the hospital, suggesting that the whole scenario was concocted. That ending did not test well with audiences and was dropped.
The 330-second Steadicam shot of Peter Fallow arriving at the Palm Court of the Winter Garden was a tour de force for operator Larry McConkey. He had to track backwards, get on a golf cart, ride it for 380 ft, get off it again, track backwards 234 ft, get into the elevator, get out again, and track for another 250 ft.