Every ‘Dirty Harry’ Movie Ranked Worst To Best

The legendary Clint Eastwood turns 92 this year, and it seems like after one of the longest careers in Hollywood, he’s finally settling down. It’s ironic that Eastwood’s retirement comes thirty years after his film Unforgiven was released; the western epic was seemingly the “summation” of all of his characters up until that point, but Eastwood continued to direct and act for another three decades. Eastwood’s final film Cry Macho was released in theaters and on HBO Max last fall, but if there’s one thing you shouldn’t do, it’s to count him out of the game entirely.

Before he stepped behind the camera for the first time with Play Misty For Me, Eastwood gained international acclaim thanks to his breakout performance in Sergio Leone’s “The Man With No Name Trilogy.” It was hardly the last time he’d portray a grim, masochistic anti-hero. 1971’s Dirty Harry changed the course of action cinema with its gritty intensity.

Compared to the lighter action farce that was popular in the ‘60s, the Dirty Harry series grounded its depiction of true crime in reality. Eastwood’s character Harry Callahan became one of his most iconic characters; he’s still associated with some of the hard-boiled detective’s most memorable one-liners.

Dirty Harry was followed by four sequels, and the entire series is now streaming on HBO Max. While it’s inevitable that every franchise will be rebooted at some point, it’s hard to imagine anyone being able to fill Eastwood’s shoes. Here are all five Dirty Harry movies, ranked worst to best.

5. The Dead Pool (1988)

While the original Dirty Harry stood out for its commitment to realism, the final film in the series pushed the franchise closer to absurdity. Callahan is known to make some smirky comments, but The Dead Pool is so focused on coining catchphrases that any semblance of stakes is absent. The film follows Callahan’s mission to hunt down a serial killer that targets prominent public figures, including himself. He’s tasked with protecting the gossip journalist Samantha Walker (Patricia Clarkson).

At 91 minutes, The Dead Pool is light on any actual mystery. The film goes to exaggerated lengths to frame the music video director Peter Swan (Liam Neeson) as the culprit that it’s obvious there will be a twist at some point. Even Eastwood seems bored by the eventual revelation. The Dead Pool isn’t unwatchable, as a memorable over-the-top performance by Jim Carrey at least makes it enjoyable, but it’s the most forgettable in the series.

4. The Enforcer (1976)

While the first two Dirty Harry films are certainly landmarks of action cinema, they’re first and foremost detective stories. Callahan was an engaging character because he was actually solving the case alongside the audience, and the films did a good job at blending suspense within the setpieces. This started to disappear by the third film The Enforcer, which goes the shoot em’ up route instead.

The Enforcer focuses on Callahan’s search for the elusive crime boss Bobby Maxwell (DeVeren Bookwalter), and for the most part the “cat and mouse” premise is entertaining. By the third installment, Callahan’s initial sense of honor became more implausible given the ruthlessness of the material, but the film does at least offer a different perspective. Callahan teams up with the new character Inspector Kate Moore (Tay Daly), and for once one of his partners actually questions his worldview.

3. Sudden Impact (1983)

The fourth film in the series was the only installment that Eastwood directed himself. Having already been in the director’s chair for over a decade, Eastwood had found his groove telling fast-paced stories with frequently disturbing material. While Sudden Impact is just as action-packed as The Enforcer, it’s by far the bloodiest installment. Eastwood was able to retain some gravitas to the series after The Enforcer pushed it further into camp.

Sudden Impact picks up with an older and more cynical Callahan, who for once somewhat sympathizes with his chief target. The con artist Jennifer Spencer (Sondra Lock) takes vengeance on a gang of traffickers that committed horrible acts of violence against her, and Callahan can empathize with her desire for justice. The sexual politics and depiction of assault haven’t aged well, but it was a more mature theme to tackle that indicated Eastwood’s more ambitious aspirations as a filmmaker.

2. Magnum Force (1973)

It was honestly a fairly difficult decision as to which film would take the top spot. Magnum Force is an excellent neo-noir crime thriller, and tackles prevalent themes of police corruption and conspiracy. Although the later entries in the series used Callahan’s conflicts with authority for comic relief, Magnum Force put him up against the systemic coverup within the San Francisco Police Department. He’s always been a maverick, but for once, Callahan actually felt like an outsider within his profession. The sharp script by Apocalypse Now and Conan the Barbarian scribe John Milus is the most thoughtful of the five films.

Callahan begins tracking down a group of vigilante cops that enact their own, cruel form of “justice;” as he uncovers the violent abuse of the badge, Callahan is forced to question his own tactics. As he weighs deeper into the conspiracy, Callahan discovers that the entire force he’s dedicated his life to is facing serious questions of legitimacy, and his entire career may have been in vain. Hal Halbrook delivers a genuinely terrifying performance as the villainous insider Lieutenant Neil Briggs. Holbrook’s dramatic background made Briggs a cut above the “villain-of-the-week” style antagonists of the other sequels.

1. Dirty Harry (1971)

As underrated as Magnum Force is, it can’t quite match the impact of the original classic. Dirty Harry doesn’t completely absolve Callahan’s behavior or lionize his worldview; it simply pits him within a deadly chase to take down the best villain of the series, the sniper Scorpio (Andy Robinson). Scorpio’s precise assassinations are methodically incorporated throughout, and the film doesn’t sensationalize the acts of realistic violence for the sake of being a crowd pleaser.

Dirty Harry was directed by Don Siegel, a Hollywood veteran whose acclaimed filmography includes the original Invasion of the Body Snatchers, Escape From Alcatraz, and The Shootist. Siegel takes time to develop Callahan’s worldview, and explores his frustrations with inaction when Scorpio threatens innocent civilians. While all the films are products of the era in which they were released, Dirty Harry has more in common with the gritty New Hollywood crime dramas like Dog Day Afternoon and Serpico than it does just another star vehicle.