When Oliver Stone decided to make his controversial "JFK" he knew his film would be debated since he was presenting countless challenges on facts concerning the assassination of President Kennedy. What Oliver couldn't predict was the appearance of films that followed his conspiracy theories on the same subject, although none of these films, including "Ruby", caused impact on anything. More than that, none of these films had the same material quality "JFK" had, a film with so much to handle in terms of characters and situations that never gets boring or complicated.
Now, John Mackenzie's "Ruby" is a wildly confusing film focused on Jack Ruby, the mysterious nightclub owner who murdered Lee Harvey Oswald, the man who (some say) shot Kennedy in Dallas, in 1963. Ruby, played with some good effort by Danny Aiello, is presented as someone similar like Oswald, a ingenuous patsy who joined the wrong people (the Mafia) for one cause and for reasons unknown was betrayed by his so-called friends who opted for killing the president. The movie gets even deeper by showing that Ruby was some sort of a informant for the government pretending to be part of the Mafia, meeting guys like Gambini and other powerful mobsters, who were plotting to kill Fidel Castro but for some reason they changed planes and decided to take Kennedy out of the picture. To make things worst, the movie chooses to include a fictional character, the stripper Candy Cane (Sherilyn Fenn) who works for Ruby, and in terms of script she's a composition between Marilyn Monroe, Ruby's girlfriend and a woman who had affairs with mobsters and even Kennedy. We hardly know who is she in the picture and how important she is besides being the wildest thing on Jack's club. What about the mysterious Maxwell (played by Arliss Howard, very good here)? Who was that guy? Part of CIA? Mafia? He always bothers Ruby but never reveals himself except the original planning about dealing with Castro. The connections between characters and situations might have worked in real life but in the film it fails at horrible levels, to the point of unbelievable.
Compared with "JFK" this film is easy to follow but it never achieves greatness; it doesn't shine a light to new facts on Kennedy's and Oswald's murders; it can only confuses with more and more things. Structurally speaking, the whole film is a mess, slow at the beginning and very rushed towards the ending and that combination ruined the suspense and made a boring drama who had some good moments. The lamest of contradictions presented was the fact of Ruby being a patriotic man, who deals with the Mafia, a bad job for his country and at the same time cries out loud when he finally realizes his own people will kill the President. It's okay to do illegal things, not pay taxes and the government but you can't kill this nation's leader.
It's quite watchable but when you analyzes the material the director had in the hands you know he could have done better than this. 5/10