Douglas leads a gang that robs half a million dollars from O'Connell. The only survivor of the gang, Douglas ties up the loot in a pair of ladies' bloomers and drops it into a rattlesnake pit for safekeeping. Later the depressed O'Connell visits the local brothel. Since he doesn't have any money, the madam lets him look through a peephole at another client enjoying the company of two of the girls. He recognizes the man as the one who robbed him and soon Douglas has been arrested by sheriff Fonda and shipped off to the territorial prison. There Douglas soon establishes himself as top dog,and when the warden, Gabel, finds out about the still-hidden loot, he offers to let Douglas escape in return for a share. Before their scheme can succeed, Gabel is killed by a Chinese prisoner during a brawl. The new warden is Fonda, now walking with a limp now after being shot by Oates, also a prisoner. A reformer, Fonda tries to work with Douglas to improve conditions at the prison, while the convict is using the privileges Fonda has given him to plan a breakout with Oates. Homosexual confidence men Cronyn and Randolph, and Meredith, a former outlaw terror turned into a fearful old man by decades in stir, are also in on the plan. Fonda invites the governor for an inspection, and Douglas uses the opportunity to escape. He double-crosses all his cohorts and escapes alone, with a betrayed and angry Fonda in pursuit. Douglas reaches the snake pit and uses his pistol to shoot the rattlers. Then he wraps his arm in his jacket and reaches down to retrieve the bloomers. When he unties them, though, a snake springs out and bites him on the neck. Within minutes Douglas is dead. Fonda arrives shortly thereafter and throws Douglas' body over the saddle of his horse and, with the money, heads back to the prison. When he arrives near the gates he contemplates the place, then the money, and after slapping the horse carrying Douglas toward the prison, Fonda rides off toward Mexico with the loot. One of the most cynical and bitterly funny westerns ever made, THERE WAS A CROOKED MAN was written by the same team that wrote BONNIE AND CLYDE (1967), Benton and Newman. They had written the script at the suggestion of Warner Bros. production chief Kenneth Hyman and titled it "Hell." The script was then rewritten several times and continually rejected before director Mankiewicz finally got a look at the original script and decided it was just what he was looking for. The biggest problem the writers and the director had was charting and explaining Fonda's change of heart as he gradually takes on a number of the characteristics of his nemesis, Douglas. Because the film had to be kept to about two hours in length, the scenes Benton and Newman wrote explaining Fonda's transformation were cut. (Reportedly, the most notable omission is a long scene between Fonda and Lee Grant that was reduced to three mostly meaningless lines in the final release.) Indeed, most of the criticism leveled at the film resulted from Fonda's unexplained character switch. In other areas, though, the film was more successful. Meredith is terrific as the Missouri Kid, who has grown old in prison and who grows marijuana in his cell. In the scene where he's asked to join the escape plot he changes from an old man ("You don't want an old coot like me") to the outlaw terror he once was ("Look, pissant, this is the Missouri Kid you're talking to") in the space of a single scene. When the time comes for him to escape, though, Meredith refuses, afraid to leave the prison that has for too long been his home. The details of the prison--built in the California desert at a cost of $300,000--are perfect, evidence of the extensive research done by Benton and Newman. So concerned with authenticity was Mankiewicz that he ordered that none of the horse manure be cleaned off the set. Despite these charms, the film proved too bitter for the public to swallow and it was only slightly successful at the box office.