The character of Dixie Dwyer is likely based on actor George Raft. Raft grew up dirt poor in New York's Hell's Kitchen. As a young man he worked as a driver/gopher for gangster Owney Madden (also depicted in this film). After his stint working for Madden he went to California and tried his hand at acting, eventually achieving considerable success playing tough-guy roles in various gangster movies, performances he based largely on Madden and Bugsy Siegel, with whom Raft was known to associate.
When Dixie and his family leave the Cotton Club, two small black kids are dancing on the sidewalk for spare change. They are clearly intended to be The Nicholas Brothers, who began dancing at the Cotton Club soon after this. In fact, however, they were already established vaudeville performers in 1928.
Although the film features several fictional murders, it is associated with one real-life murder. When Robert Evans was raising money for the film, he became associated with a promoter named Roy Radin. Radin was reportedly murdered on May 13, 1983, but his body was not found for several weeks. Evans was not accused of murder but was implicated in the investigation because he was dealing with Radin and Karen Jacobs-Greenberger, who introduced Radin to Evans. She was convicted of ordering the murder of Radin and is serving a life sentence for the crime.
As depicted in the movie, Owney Madden and Big Frenchy DeMange were close friends and partners in the Cotton Club. Ironically, as younger men they belonged to rival crime syndicates and were bitter enemies.
The film was a pet project of Robert Evans. He struggled to spark interest among backers in Mario Puzo's script (early donors included Saudi arms dealer Adnan Khashoggi, whose money Evans had to return after rejecting his suggested script changes).
Enticed by a script by Mario Puzo and the promise of funding from Las Vegas casino-owning brothers Edward Doumani and Fred Doumani, Paramount offered producer Robert Evans the talents of Richard Gere as leading man and access to its studio facilities along with further production funds. However, determined to re-establish his reputation as a major player in Hollywood, Evans turned down the latter offer in favor of the services of Orion Pictures--which was in the business of marketing and distributing films rather than producing them, meaning that Evans would need to raise more production money and find a studio in which to shoot the film, causing further delays and adding to the already bloated budget.
Upon being appointed director, Francis Ford Coppola added to the budgetary woes by firing the film crew Robert Evans had assembled en masse (in some cases requiring large payoffs) and hiring his own crew members, including a music arranger who commuted via Concorde between the shoot in New York and a regular engagement in Switzerland.
Francis Ford Coppola's quasi-improvisational approach to directing the actors meant the script was in a constant state of flux, and actors would frequently spend all day on set without shooting a single frame of film.
Inspired to make the film by a picture-book history of the famous nightclub by James Haskins, Robert Evans also wanted to direct. He hired William Kennedy and Francis Ford Coppola to re-write Mario Puzo's story and screenplay. Evans eventually decided that he did not want to direct the film and asked Coppola at the last minute.
Richard Sylbert claimed that he told Robert Evans not to hire Francis Ford Coppola because "he resents being in the commercial, narrative, Hollywood movie business". Coppola claimed that he had letters from Sylbert that asked him to work on the film because Evans was crazy. The director also said that "Evans set the tone for the level of extravagance long before I got there".
Victor L. Sayyah filed a lawsuit against investors Edward Doumani and Fred Doumani, their lawyer David Hurwitz, Robert Evans and Orion Pictures for fraud and breach of contract. Sayyah invested $5 million and claimed that he had little chance of recouping his money because the budget escalated from $25 to $58 million. He accused the Doumanis of forcing out Evans and that an Orion loan to the film of $15 million unnecessarily increased the budget. Evans, in turn, sued Edward Doumani to keep from acting as general partner on the film.
Allegedly, the reconciliation scene between Owney Madden and Frenchy was written by Fred Gwynne. Francis Ford Coppola considered removing the scene during editing but was convinced by co-screenwriter William Kennedy to leave it in.
There were frequent clashes between Francis Ford Coppola and Richard Gere, who insisted on showing off his (modest) skills on the cornet in the film, and seemed more concerned about possible damage to his reputation than about the film itself.
The trivia item below may give away important plot points.
The Nicolas Cage character, Vincent "Mad Dog" Dwyer, was based on an actual Irish gangster named Vincent "Mad Dog" Coll Cage is also the nephew of director Francis Ford Coppola). In real life, Coll was a young hothead who started a bootlegging war with Dutch Schultz in 1931. As in the film, Coll was responsible for a drive-by shooting where he and his henchmen tried to kill one of Schultz's men, but a child playing on the street was accidentally killed (in the film, the child who is killed in the shooting is played by a young Sofia Coppola). Also, like Dwyer, Coll was shot to death by Scultz's men while making calls in a drugstore telephone booth.