But make no mistake: There Was a Crooked Man is a lousy movie. Directed by Joseph L. Mankiewicz -- a long way from All About Eve at this point -- this Western stars Kirk Douglas as Paris Pittman, a no-good thief and killer who somehow manages to routinely steal from people designed by the filmmakers to be seen as more obectionable than he. Not the least of his victims' crimes is, of course, that they're rich, but they're also smug, and they live in big houses like jerks. Pittman, on the other hand, is insouciant, and "funny", disdains authority, and he likes to bone chicks. This film was made in 1970, so with those last two facts Benton and Newman were already halfway towards winning sympathy for their anti-hero from the target audience, that target audience being college kids who hated cops and were tired of being hassled all the time.
Pittman gets arrested for the robbery that begins the film, and finds himself in prison with a motley group of misfit ne'er-do-wells portrayed by, among others, Burgess Meredith, Warren Oates, John Randolph and Hume Cronyn (by the way, I didn't realize Cronyn played the character Dudley until the end credits. Cronyn is essentially doing an impersonation of Paul Lynde here, and the whole time I was watching this I was thinking, "That's not Paul Lynde, that's the other guy." I don't know who I thought the "other guy" was, but apparently it was Hume Cronyn). A sheriff who pops up early in the movie, and later goes on to become warden of the prison where most of the film takes place, is played by Henry Fonda, and Fonda embodies a kind of "progressive" law enforcement philosophy, in that he wishes that all the other policemen and prison officials would quit acting like cartoon villains all the time. I'm with him on that, but Kirk Douglas likes to point out to Fonda that he may think he's a good man, but he's not, because he's going to allow a young prisoner (played by Michael Blodgett) to be hanged even though the death he caused was accidental. That kind of deck-stacking plotting and self-righteous dialogue being delivered by a murderer was a specialty of aggressively edgy, pseudo-satirical genre films of the time period, and while those films grubbed for applause from those in its audience who sympathized with the filmmakers worldviews, I promise you that if any member of that audience tried to act out that worldview at the expense of, say, Robert Benton, David Newman or Joseph L. Mankiewicz, the pigs would be summoned, but quick.
So, anyway, as you probably guessed, a prison break is planned and carried out, and here's where I get into some trouble. Douglas's behavior during the prison break is villainous in such a way that I have a hard time believing that the filmmakers condone it, or even believe it's fun. Now, I'm also not saying that, up until this point, the filmmakers had been condoning murder in any way, but certain killings are portrayed as being, at best, the cost of doing business for someone like Pittman and his cronies, and plus, the victims aren't such great people either! But towards the end of the prison break, I feel like Benton and Newman want the audience to at least believe that Pittman has crossed a line, and I'm even willing to consider the argument that this line-crossing is intended to make the audience reflect on the fact that they've been rooting for this murderer for two hours, and that maybe they shouldn't have been. Add to that the fact that Pittman's fate is delivered with an air of comeuppance, and I have to concede that while it's all clumsily handled, and the movie isn't any good anyway, and I don't really buy the best-case scenario I just laid out, it is, at least, something.
And then, of course, we get a little epilogue that informs us that while murder may be wrong, stealing is encouraged. Two steps forward, one step back. At best.