There was a crooked man (released in 1970) - starring Kirk Douglas, Henry Fonda, a comedy western film

This black comedy western is directed by Joseph L. Mankiewicz and star Kirk Douglas and Henry Fonda. Paris Pitman Jr is a bespectacled smooth talking con man and a murderer. He is a very evil man with no morals and soft feelings within him. But being a cool operator he is able to charm his way out of difficult situations and win the trust of those around him.
Pitman and his gang loot the house of a wealthy rancher, Lomax and make away with half a million dollars. But one by one the gang members are shot by the police and the surviving lone marauder is killed by Pitman himself to prevent him from claiming a share on the booty. Pitman escapes and enters a brothel. He ties the money up and drops it in a rattlers pit.
He enters the brothel, is recognized by Lomax and is subsequently arrested and sentenced to a prison Arizona. The prison is in the middle of a desert and a hard life awaits Pitman. But he tries to bribe Warden LeGoff to help him escape. His plans go awry when the warden is killed by one of the inmates and his place is taken up by an upright officer called Lopeman. Lopeman is an idealist who is in favor of prison and judicial reform. He believes in reforming the criminals and presents a slew of measures to improve the conditions in the prison.



Pitman is enraged at first at his failure, but soon wins the trust of Lopeman. Lopeman puts him in charge of the building of a new prison dining room. Soon he starts manipulating others to formulate a plan for escaping from the prison. He forms a gang of his own which includes Missouri Kid, Whinner and Macnutt (a gay con artist couple), Floyd moon, Michael Blodgett, a kid on death row and Ah Ping, a silent Chinese. All of them slowly feel the power of Pitman Jr and plot an escape. They plan to start a riot during the inspection day by the governor.
Soon the plot is successful, with full scale rioting taking place, and as a result, all of them escape from prison. But Pitman the backstabber that he is, kills every one. Lopeman sheds all his idealisms and vow to bring back Pitman dead or alive. But fate has another things in store for the outlaw. As Pitman takes out the loot from the Rattlers nest he is bitten by one of them.
This is the most cynical movie I have ever seen. There is no good vs evil fights with good triumphant over the bad. This is the story of a bad man who corrupts and manipulates his way out to meet the just desserts by the quirk of fate. Tough movie to watch on.