Paris Pitman Jr. (Kirk Douglas) is a well-known scoundrel who makes his living fleecing rich people of their fortunes. However, he’s not infallible, and one scheme results in him being caught and sent to a penitentiary, where he becomes one of a motley crew of bandits and criminals under the watchful eye of the new warden, Woodward Lopeman (Henry Fonda). Despite being a notorious career criminal, Pitman is a well-meaning man who endeavours to improve the conditions of the prison, something he shares with Lopeman, who finds the living standard of the residents deplorable, which goes against his belief that everyone, whether law-abiding or otherwise, deserves the same treatment. What the warden doesn’t realize is that beneath his attempts to help build the prison to the standard it should be, Pitman has deeper intentions – he is assembling a crew of fellow prisoners and hatching a plan to escape their new home, with each individual playing their part in what will hopefully be a successful escape. Yet, Lopeman is not as crooked or corrupt as previous wardens, and despite Pitman’s attempts to reason with him, by means of sweetening the bargain with the promise of some of his recent earnings, the warden is not someone who can be bought. However, this doesn’t stop the two men from constantly trying to usurp the other, leading to a viciously funny clash of personalities.

Joseph L. Mankiewicz had a long career in Hollywood, but despite working in an extensive range of genres, he never made a western until his penultimate film. Mankiewicz was one of the briding figures between the Golden Age and New Hollywood, and There Was a Crooked Man… feels like the perfect combination of the two styles, insofar as it blends classic western tropes with a more devil-may-care sense of social commentary, no doubt evoked by the work of David Newman and Robert Benton, still relative neophytes at this time, but on the cusp of achieving their own acclaim, especially due to the massive success of Bonnie and Clyde, a film that launched this exact kind of subversive crime thriller. There Was a Crooked Man… takes a fascinating approach to the set of genre conventions that forms its foundation, and ventures in being a hilarious subversion of a genre that was slowly declining. This film succeeds in ways that others consistently fail – it finds the balance between genres, has a distinct style and a certain charm that works in the advantage of a story that would normally be the folly of more serious fare, but is here repurposed as an outrageous comedy, one that feels authentic without ever being too concerned with plausibility. A direct descendant of the brilliant The Great Escape, which took a similar look at a group of eclectic individuals working together to flee imprisonment, but adding onto it some social commentary and more moral ambiguity, the exact kind that made  some of Mankiewicz’s other films so memorable (he was one of the few major directors during the Golden Age that consistently employed characters that were far more vague in their intentions – he was never afraid to put more reprehensible characters in the central roles), resulting in a resoundingly successful film that defies the odds normally levelled against films in this genre by feeling effortlessly fresh and vibrant in every way.

The transition between the different eras of the western genre had its apex in the 1970s, where many filmmakers, dissatisfied with the direction these films were taking, especially in how they were relatively formulaic, set out to redefine the genre, telling more unique stories in idiosyncratic ways. Mankiewicz was in an odd position – he was technically a representative of the old guard of Hollywood, yet he was still such a chameleonic director, with his work exhibiting a refusal to stay within one style, and a tendency to explore. I spoke about it briefly in my review for his final masterpiece, Sleuth, which was a daring combination of old style with new thrills. There Was a Crooked Man… is his first foray into the western genre, and not only does it demonstrate that he was still fully in command of his craft later on in his career, but also that he was able to still reinvent a genre that had been omnipotent for decades, working with the terrific screenplay by Benton and Newman to make one of the most entertaining, but smartest and enduring entries into the genre. There are many merits in this film, which is the product of some excellent symbiosis between a distinct group of artists working together to reconcile two very different cinematic movements into a single thrilling piece that is as entertaining as it is thought-provoking. There are very few flaws if any, that can be found in There Was a Crooked Man…, which Mankiewicz proving himself to still possess that rebellious talent that made him such a compelling and brilliant director right from the outset.

There Was a Crooked Man…, like many films that follow this kind of pattern, employs an exceptional cast of eclectic performers, all of which were astounding, playing off their natural charms in characters that were not necessarily out of their wheelhouse, but nonetheless very different from what we normally expect from them. Leading the film is Kirk Douglas, who is at his scruffiest as the unconventional hero of the piece, the career criminal who made the unfortunate decision of allowing himself to be caught through sheer momentary incompetence. He’s contrasted by Henry Fonda, who is at his most regal in the role of the good-nature, mild-mannered U.S. Marshall who is sent to prison, albeit in a different capacity, being selected to run the penitentiary as the new warden. So much of There Was a Crooked Man… depends on the relationship between Fonda and Douglas, with the foundation being built on how these two men from very different sides of the law find themselves working together for what they think is a common goal, but which proves to be almost entirely the opposite. The chemistry between these two extraordinary actors was palpable, no less because much like the director of the film, both of them found themselves flourishing in the classical era, as well as the later stages of the film industry, where their talents as veterans willing to play roles that go against typecasting made them exceptionally valuable to new and burgeoning filmmakers looking to gain some credibility, the kind that comes with having stars of this magnitude.

Yet, it’s not only these two actors who make There Was a Crooked Man… so compelling –  Mankiewicz takes on a wide array of character actors in supporting roles. The likes of Hume Cronyn, Warren Oates, Burgess Meredith and John Randolph all appear in smaller but pivotal roles as fellow prisoners, giving exceptionally funny performances that result from a screenplay that gives each character a distinct personality, and the experience of the actors, who take the opportunity to play such eccentric individuals in their stride. The cast is the most significant indicator that the film was blending different generations of filmmaking in this exceptionally entertaining revisionist western. However, a close reading of the film reveals there’s a great deal more Mankiewicz does in terms of finding common ground. Visually, the film has the striking beauty of the classical westerns, combined with some of the gritty, almost bleak realism that came later on, where the triumphant landscapes were eventually replaced with smaller, more intimate settings. The prison that forms the centrepiece of the film is a great example of this – it is simple, real and doesn’t have any distinct flourishes, and while we can argue that this is a case of a location becoming a character on its own, it’s less because of how omnipotent it is, but how the banality of the prison serves to underpin the despair of the people inside, both prisoners and authorities. This links directly to the more thematic conventions, where Mankiewicz is questioning some of the moral values of previous westerns – There Was a Crooked Man… is a film centred on criminals, yet the director never offers a clear definition between good and evil. None of the characters in the film can ever qualify as heroes or villains. Everyone is morally ambigious, with vague motives and an equal tendency to occasionally conduct themselves in unsavoury ways. Even the character of Lopeman, who is constructed as the epitome of innocence, finds himself falling victim to the threat of corruption. The film’s title is quite evocative, but also very vague: we never quite know who the “crooked man” is, but it is very likely that it doesn’t refer to one individual, but rather to a collective. The film mercifully doesn’t preach, which makes its view of morality all the more compelling, because it’s more intent on telling a story than conveying an overwrought message.

There Was a Crooked Man… is a terrific film, solely because it is, more than anything else, a clear attempt to have some fun with a great concept, which sought to gently make fun of the western genre, the distilled version of which was already steadily declining in favour of more subversive and challenging works. There’s not too much underlying this film other than the investigations into moral ambiguity that it thrives on, and a certain social message that isn’t initially clear, mainly because it is very broad and also not made to be all that prominent. It is ultimately an offbeat western comedy that treats its subject with respect, without becoming victim to the same tropes or conventions that normally find their way into these kinds of films. Whether through the excellent script by Benton and Newman, the magnificent performances, from which Douglas and Fonda are clear standouts, or the dedicated vision of Mankiewicz, who guides the film and turns it into one of the most fascinating experiments within a dated genre. Somehow, There Was a Crooked Man… remains just as enthralling and fascinating as it was nearly half a century ago, and its humour, pathos and underlying brilliance, both creatively and thematically, all work together to create a truly memorable western that has the thrills of the classical era, and the intelligence of the revisionist period – and is an extraordinary achievement, and a resounding triumph in every way.