Clint Eastwood is, perhaps, the last of a breed—that of the American cinematic icon. His peers may include the likes of Tom Cruise, yet Eastwood’s presence carries an unmistakably American essence, one that is largely absent from today’s globalized cinema. Eastwood, with his trademark scowl, and sarcastic, squinty-eyed glare, dismantled classic American archetypes like the white-hatted cowboy made popular by John Wayne and James Stewart. In the place of heroes, he offered unforgettable and complex characters like the Man with No Name, Josey Wales, and William Munny. Beyond this, he has successfully managed to navigate an industry that is often harsh to aging stars. With a career spanning more than half a century and marked by two Oscar wins as a director, Eastwood’s legacy remains an impressive testament to endurance and adaptability.

Callahan straddles the line between violence and compassion, law and justice, becoming an embodiment of a uniquely urban—and distinctively American—strain of conflicted, Byronic hero.

And then, there’s Dirty Harry Callahan—an archetype unto himself, who frequently lives in the shadow of Eastwood’s better-known western characters. But for over a decade in the ‘70s and ‘80s, Eastwood traded his six-gun for a Smith & Wesson Model 29 chambering a .44 Magnum round, to deconstruct the crime film and classic cop heroes. Callahan was a rule-bender, known for his ruthless tactics and his disdain for bureaucratic red tape, and there is hardly a scenario in which a film like Dirty Harry (1971) could be made today without significant blowback, primarily due to the perceived politically conservative attitude the film possesses—despite the fact that Eastwood has consistently maintained that all he and production partner Don Siegel set out to do was make an entertaining and compelling detective thriller.

Watching the Dirty Harry films again recently, I was struck less by their political undertones and more by the character of Harry himself. Though the five films span over a decade in time (1971–1988), I watched them over a span of five nights, and began noticing a fascinating character arc that only became more pronounced as the films went on. There is a certain rough-around-the-edges compassion that emerges in Harry over the course of these films. This is not the compassion of a pacifist, but rather the compassion of a man who understands that sometimes, to protect the sheep, the shepherd must get down and dirty with the wolves.

Callahan is introduced in the 1971 original film as a tough, no-nonsense, and principled detective hunting down a serial killer called Scorpio (Andy Robinson). Throughout the narrative, Callahan walks a fine line between protecting the innocent and using his badge as an excuse to beat on criminals he deems worthy of punishment. The film is surprisingly barren of character development—which just goes to show you that classics actually can be made by not following the “rules” of cinematic storytelling. Scorpio is, seemingly, without motive. He is simply insane, and Robinson plays this role with a chilling efficiency—this is a reviling character, not one of those villains that viewers “love to hate,” but one of those that you simply want gone. There is no rehabilitating Scorpio, no medication to cure him. He is not even that bright. He makes mistakes. He gets caught. But a very optimistically minded judicial system keeps giving him leeway, which he exploits time and again.

Harry himself is a vague outline, and the question of whether he is an honest cop or a legal vigilante is up for debate. Yet the final confrontation between these two silhouettes is without doubt one of the most satisfying endings to any thriller and is a very clever way of bringing the narrative full circle. “I know what you’re thinking, punk,” Harry intones, the opening of his trademark taunt that attempts to coax the culprit he is holding at gunpoint into trying something foolish. And the pulse of the viewer quickens because they know that Harry knows this Scorpio character is just insane enough to try something foolish. 

The final moments are as poignant as they are disturbing, with Harry having goaded an unarmed man into arming himself just to exploit the legal loophole that would justify Harry blowing him away. Yet the final shot is of Harry, looking at his badge, disgusted with the rigid police force that allowed Scorpio’s reign of terror to go on for as long as it did—and maybe just as disgusted with himself for blurring the line between cop and criminal—before hurling it aside and walking away. On its own, the film works as a pure and riveting distillation of ‘70s crime thrillers—but as the first of a series, the film sets the stage for a fascinating character study.

Nineteen seventy-three’s sequel, Magnum Force, brilliantly turns Harry’s principles against him. The original film often found his superiors questioning Harry’s judgment—part of what makes that film so compelling is simply watching Harry be right about Scorpio at every turn, while the optimists in the room wear plastic smiles and play their political games as innocent people keep dying. But in Magnum Force, Harry finds himself up against a group of rogue cops who idolize him, taking his methods to frightening extremes. 

The film sees Harry grapple with the realization that justice untethered from accountability is quite indistinguishable from tyranny. During a confrontation with the officers, one of them explains that the court system has failed to administer justice, that violence is the only recourse, and that Harry, of all people, should understand that. The words the officers speak are words that Harry himself could have spoken at the conclusion of the last film, and the confrontation forces him to mature in his understanding of where the edges of the law lie.

The Enforcer (1976) pairs Harry with the plucky and fearless Kate Moore, portrayed by Tyne Daly of Cagney & Lacey (1981–88) fame. His initial resistance to working with a woman (contextually, his initial objections are less misogynistic than some critics might think) gives way to respect and acceptance, demonstrating a newfound sense of empathy. Harry’s evolution from grudging acceptance to genuine respect for Moore hints at a softer, more compassionate side beginning to emerge. Time, age, and experience has begun tempering Harry, setting up the series’ darkest entry.

Sudden Impact is a grueling film. After the more lighthearted take on the series that was The Enforcer, this 1983 sequel sees rape victim Jennifer Spencer (Sondra Locke) take the reins of justice into her own hands and embark upon a killing spree. Driven by revenge, her path crosses with Harry’s at key points as he unravels the dense plot. Though he does not condone her methods, he sympathizes with her pain and, remarkably, supports her pursuit of justice to the point where he begins intentionally misleading his fellow officers to ensure that Spencer is vindicated.

The final film, 1988’s The Dead Pool, offers a more seasoned and contemplative Harry who takes on the dark side of fame and notoriety. Though he is unafraid to use violence, he is noticeably more measured as a law enforcement officer, indicating a man matured by his experiences. Harry Callahan in The Dead Pool is quite different from “Dirty” Harry Callahan whom viewers were introduced to almost two decades prior.

Despite his growth and development as a character, Harry remains a morally complex figure throughout the series. He consistently flirts with the boundaries of the law and justice, defining and redefining them as the world shifts around him, suggesting a deep-seated belief that the two are not always aligned. His growing compassion is framed by this understanding, adding a layer of complexity to his character arc.

What are Christians to make of these sorts of movies? Harry is certainly not a Christ figure in any traditional sense—although you might get some mileage out of evaluating the sense of justice and retribution that Jesus of Revelation visits upon his enemies (Rev. 19:11-21). But Harry does evolve throughout the series, there is no denying that. And this evolution is a slow, sometimes stumbling, journey toward the principles of understanding, empathy, and compassion. Yet his actions often challenge these principles, highlighting the contradiction inherent in his character—a contradiction that is, perhaps, present in all of us.

The late Brennan Manning once wrote

When I get honest, I admit I am a bundle of paradoxes. I believe and I doubt, I hope and get discouraged, I love and I hate, I feel bad about feeling good, I feel guilty about not feeling guilty. I am trusting and suspicious. I am honest and I still play games. Aristotle said that I am a rational animal; I say I am an angel with an incredible capacity for beer.

As goes Manning, so goes Callahan. His willingness to do whatever it takes to ensure that justice is served, even when it means skirting the law, underpins his understanding of compassion. A conflicted, contradictory, complex understanding, but one that is capable of growth and development.

Harry Callahan straddles the line between violence and compassion, law and justice, becoming an embodiment of a uniquely urban—and distinctively American—strain of conflicted, Byronic hero. As jewels are formed under immense pressure, so is Harry’s compassion shaped and honed by the challenges and tragedies he faces.

Are the Dirty Harry films must-see viewing? No. But are they worthwhile? Well, considering that Hollywood today seems to work overtime to infantilize audiences, and fewer and fewer big-budget films are made for emotionally well-adjusted, red-blooded adults, one could do far worse than spend two hours watching Clint Eastwood scowl at criminals and courthouse employees alike. Eastwood is still around, haunting the wings of studios and occasionally churning out a banger of a film. But there is no denying that Hollywood “don’t make ‘em” like Dirty Harry anymore.

And, to quote Callahan himself, “That’s a helluva price to pay for being stylish.”