Will Penny is a bit of an off-kilter experience, with regards to the western. It arrived in the era of Peckinpah, the spaghetti western, and John Wayne’s distinctively republican leaning throwbacks. Yet it doesn’t resemble these even remotely. It’s a strange slice of the western experience, focusing on a loner cowboy and his deepening relationship with a woman and her young boy. Tom Gries directs this film with a remarkable sensitivity to the human elements: from the open and reflective nature the film takes toward the concept of the masculine identiy, to the spirited respect the film pays to the female perspective. Ultimately the film succeeds because of an engaging script, some extremely well-drawn performances, and a tone that’s both melancholy, self-aware, and contains just enough trappings of the western genre that we don’t forget we’re watching a western.
Heston apparently liked this film above any other film that he ever appeared in. It’s not hard to imagine why he would feel that way. The film is based upon a television episode of The Westerner from 1960 (created by Peckinpah) that Gries had written and directed himself. It’s easy to see how Gries became very familiar with how he wanted this film to be. He thus also wrote and directed Will Penny, and the flair for how this movie looks and sounds is all his own. Heston stars as Will Penny, a loner cowboy, who goes from one job to the next. Between work, he and a few other cowboys become entangled in a skirmish with a really weird, cultish family, headed by Preacher Quint (a whacked out Donald Pleasance). Penny kills one of the family members in the fight. He moves on and through his travels encounters a woman named Catherine (Joan Hackett) and her boy Horace (Tom Gries’s real-life son Jon Gries) in mid-travels at an inn. He then moves on again and happens upon a job tending a remote section of a huge cattle range over the winter led by foreman Alex (Ben Johnson). When Penny arrives to his assigned shack, he finds Catherine and Horace squatting there. She threatens to shoot him, so he tells her she has a few days to leave due to his boss’s demands. While he’s off riding, the Quints ambush Penny in revenge. Near death, Penny returns to the shack, where Catherine nurses him to health and slowly but surely, the trio of Penny, Catherine, and Horace begin to form a family unit. Until of course, there is a fateful showdown with the Quints, and Penny is forced to make some tough decisions.
The amount of investment given to pacing in this film is key. Penny and Catherine and Horace are not thrust together too early in the film. Their events are allowed to arc slowly together until they intersect in a natural way. Even though we suspect they will find each other later, it’s not due to anything that feels emotionally disconnected or forced. The film earns every moment. Part of a direct appeal of this film, in fact, is the dialogue between Penny and Catherine as they exchange feelings and ideas. Their relationship is one of the most tenderhearted and romantic in all of western-dom. In fact Catherine’s character is one of the great female roles in any western. She shoots her own gun, bosses around Penny, pursues him sexually, thwarts the bad guys, even proposes marriage to Penny. It’s a full-blooded, well envisioned female role, the likes of which I’m afraid to say are not common enough in films like this. But Heston’s Penny is also a well-rounded character. He’s sensitive to the point of nearly crying at one point in the film. Gries doesn’t just demystify the cowboy psychology, allowing Penny to be vulnerable and humble, but also the cowboy physicality. Penny gets shot at, ambushed, pushed around, humiliated, and emasculated and doesn’t always have an answer for all of these things. He’s fallible, awkward and real. It’s one of Heston’s greatest achievements. The film’s backbone are these characters and these progressive thoughts.
But that’s not to say the film is devoid of excitement. The Quints, in particular, Donald Pleasance are frightening. Pleasance plays the Preacher with a wild eyed unhinged freedom. You’re not sure at all of what he’s capable of doing next. Even his accent is unpredictable! He somehow blends his English accent with shades of southern inflection and cowboy drawl. So bizarre! He’s one of the great villains. The final 20 minutes or so of the film where the Quints overtake Penny, Catherine and Horace in the shack, are a queasy, unsettling mix of terror and fiendishly comedic bravado. We can’t help but be a bit amused at Pleasance’s weirdness, but we’re afraid he and his cohorts are going to kill our likeable heroes. Ultimately, though, the film's greatest suspense comes at the end, where Penny must decide whether to stay with Catherine and Horace or to continue on his loner path. It’s here that the film makes the appropriate and less sentimental choice of having him ride off into the sunset, leaving Catherine and Horace as he feels it’s the right thing to do. Gries’s deft writing allows for the psychology of the people to be laid bare, but maintains an appropriate sense of the cowboy myth at the same time. One could say that the film wants to have its cake and eat it too, but to that I would reply that Penny's decision feels like the decision that this particular individual would make in that situation. We understand him well enough to know that his self-doubt and fear keep him from choosing the family as his future. If anything, it’s the most realistic and truth-based conclusion that this extremely honest film could come to.