On the morning of November 24, 1963, while being transferred from a jail cell to an interrogation office, Lee Harvey Oswald was shot by Jack Ruby, a Dallas nightclub owner, allegedly acting out of rage and anguish over the death of the president. Ruby was tried and found guilty of murder (March 14, 1964) and was sentenced to death. In October 1966 a Texas appeals court reversed the conviction, but, before a new trial could be held, Ruby died of a blood clot, complicated by cancer (Jan. 3, 1967).
Danny Aiello replaced Bob Hoskins in the central role of Jack Ruby. Hoskins was originally signed to play Ruby but filming delays meant that he had to report for duty on the set of Steven Spielberg's Hook (1991). Hoskins and this film's director John Mackenzie had previously collaborated on two cinema movie collaborations. These were the theatrical feature films Beyond the Limit (1983), and the first, The Long Good Friday (1980).
The character of Sheryl Ann 'Candy Cane' DuJean, portrayed by Sherilyn Fenn, is a fictitious character. However, she is a composite of several real-life women including stripper Candy Barr (who befriended Jack Ruby), Marilyn Monroe (of whom Candy Cane is a look-alike) and Judith Campbell Exner (who said she had affairs with both Sam Giancana and John F. Kennedy).
Danny Aiello said that, out of all the roles he'd played, the title role of Jack Ruby was his favorite. He cited the diversity of Ruby's character and his skill at effortlessly blending into any social setting as to what made it his favorite role.