James Cagney had been advised by his doctors and caregivers that making a film at this point in his life was very important for his health. The actor never flew, so he and his wife took an ocean liner to London, where his scenes were filmed. It is a tribute to his professionalism that despite his numerous infirmities, he generously stayed on set during his fellow actors' closeups to give them line readings.
Because of the presence of the ailing James Cagney (in what would prove to be his final screen appearance), the movie was officially exempted from the long-running Actors' Strike of the early 1980s - the only production afforded this honor.
When Jack Nicholson, who was to play Rhinelander Waldo, had to drop out of the film less than a month before filming began, the producers were left without a name star in the cast. It was then that director Milos Forman recruited James Cagney, whom he had met at a private dinner in Connecticut the year before. He offered Cagney any part he wanted including (facetiously) the role of Evelyn Nesbitt.
James Cagney was wheelchair-bound at the time of shooting. Most scenes show him sitting; a stand-in was used for his remaining scenes showing him on his feet (and were shot from the back to obscure the stand-in's face).
According to Milos Forman, James Cagney initially agreed to play the police chief on two conditions: he would not sign a contract of any kind, and he reserved the right to change his mind and quit the film until three days before shooting began on his scenes.
A ten-minute sequence on the Lower East Side featuring real-life social activist Emma Goldman was cut from the final print. In the sequence Goldman takes Evelyn Nesbitt back to her apartment, explains her misgivings over the use of restrictive undergarments by women, removes them from Nesbitt and tries to recruit her for her socialist cause. During the scene they are observed by a voyeuristic Younger Brother, who has followed them into the building and has been secretly observing the undressed Nesbitt.
This film reunited James Cagney (coming out of a 20-year retirement following One, Two, Three (1961)) with Pat O'Brien, his frequent co-star from the 1930s and 1940s. It was the last theatrical film for both of them.
Milos Forman originally wanted E.L. Doctorow to collaborate on the screenplay, but the novelist thought that a feature film could not do justice to his epic novel and believed that it should be done as a ten-part TV miniseries. Doctorow did not participate in the development of the screenplay.
The silhouettist played by Mandy Patinkin and his wife (played by Fran Drescher) are listed in the credits with the character names 'Tateh' and 'Mameh'. These are not meant to be interpreted as their actual names, but are rather the Yiddish words for 'father' and 'mother', respectively.