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.
Steadicam operator Larry McConkey coordinated the complex, nearly 5-minute opening tracking sequence that included a cramped ride in a service elevator. It was the first of McConkey's collaborations with Brian De Palma.
In the opening tracking shot, when Bruce Willis gets in the elevator, Brian De Palma can be seen, dressed up as a security guard. It was technically impossible for the camera crew and Brian 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.
According to Julie Salamon in "The Devil's Candy," Walter Matthau was originally offered the role of the judge, but he demanded a $1 million fee. The producers balked, and signed Alan Arkin for $150,000.
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.
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 feet, get off of it, track backwards 234 feet, get into the elevator, get out, and track for another 250 feet.
The judge role was based on famous Bronx judge Burton B. Roberts - in the book, the judge is called Myron Kovitsky and like Roberts, he's also Jewish. With high hopes, the real judge actually auditioned for the role and despite not having any acting experience he almost got the part. However, Brian De Palma wasn't fully convinced with his casting and decided to go with Walter Matthau, who wanted a million dollars as salary, which the studio refused; then went to Alan Arkin who accepted the role and would get 120.000 as salary; but later on De Palma felt the movie needed a different racial perspective feeling that it was all so negative up to that point and demanded that the judge should be played by a black actor. Morgan Freeman was the chosen actor but since at the time he was just coming from a second Oscar nomination, his salary got bigger and after a tough negotiation with the studio he settled for 650.000 - a lot more than Arkin would get had the role was kept as its origins. After the film's release, judge Roberts thought the movie stunk and that he would be a better judge than what Freeman did. (Source: Julie Salamon's book 'The Devil's Candy').
Steven Spielberg was briefly considered as a director due to its influence with the studio, who according to many insiders and Julie Salamon's book, he always gets the chance to see all the scripts sent at Warner. His personal friend Brian De Palma got the job and Spielberg even visited the set created for the movie in Los Angeles.
Though Peter Guber is still credited as executive producer for the film (in fact, he was the person who pitched the idea for the movie adaptation of Wolfe's novel), he was actually dismissed from the movie in 1989, when he left Warner Bros. to reach a bigger position at Columbia Pictures, along with his creative partner Jon Peters. For a brief moment, the film had no producers and even Steven Spielberg was invited to be a producer - but due to his friendship with Brian De Palma he declined the offer. De Palma end up being the sole producer.
Peter Guber was the original producer of the film and hired three people, whom many insiders felt were wrong for the project: writer Michael Cristofer, director Brian De Palma, and star Tom Hanks. He quit before filming began to work for another company, and even though, he is credited as Executive Producer in the opening credits, the critics didn't mention him in their reviews as they blamed Cristofer, De Palma and Hanks for the fiasco.
Michael Cristofer's original script ended with the hit-and-run victim walking out of the hospital, suggesting that the whole scenario was false. That ending was dropped, because it didn't test well with audiences.
Julie Salamon's book The Devil's Candy (about the making of the film) was named after a description made by executive producer Peter Guber when he was explaining to Brian De Palma and the casting director that the actress cast for Maria Ruskin role should be a devil's candy. Guber considered that role as the toughest one to be cast.
Tom Wolfe was always surprised that a Hollywood studio would be interested in making a film adaptation of Bonfire (his first fictional work). Though he had no complaints about the price he got for the rights and enjoying the fact he wouldn't have to write any screenplay for the film, practically abstaining himself from any involvement with it, he didn't like the film. He watched it three times and always felt there was something missing.
According to "Devil's Candy", Melanie Griffith refused to read the novel. "I'm not going to read the book. I don't know why anybody would want to. Maybe I was demanding, but that was a hard shoot too."
Producer Don Simpson wanted to act in the film, as far as volunteer for the role of the TV producer who wants to turn Sherman McCoy's story into a movie. Simpson's lobby hard for the role consisted in sending a note to Variety magazine and to De Palma. Richard Belzer was cast instead. (Source: Julie Salamon's book 'The Devil's Candy').
Brian De Palma: At the very beginning of the opening tracking shot, as the limousine carrying Bruce Willis enters the basement. De Palma is the security guard who days "Now arriving Area A" into a walkie-talkie. He hurries off-screen. He then shows up seated on the rear of the golf-cart, behind Willis and Rita Wilson, still talking into his walkie-talkie. When the cart stops, De Palma once again runs off ahead of the actors. De Palma has said in interviews that he put himself into the sequence due to the logistics of directing the lengthy and complicated take. He shaved off his beard to make himself harder to recognize.
The trivia items below may give away important plot points.
According to the book "Devil's Candy", Bruce Willis was "was generally disliked by most of the cast and crew (due to his ego)." While filming a scene in which Alan King's character dies, Willis challenged the crew to move the scene along faster, allegedly because the set was very hot. Although Brian De Palma called out Willis to discuss the incident, the scene ended up considerably shorter and simpler than originally intended.
In the film, Bronx District Attorney and New York mayoral candidate Abe Weiss stay that he hopes the city's black voters see him as the "first black District Attorney of Bronx County." In November 1988, two years before the film was released Judge Robert T. Johnson was elected the first black district attorney of the Bronx. He held the position until December 31, 2015.