The Dead Pool (1988)

Director: Buddy Van Horn

Cast: Clint Eastwood, Patricia Clarkson, Liam Neeson, Jim Carrey

Have I Seen it Before: Never. And now I’ve seen all of the Dirty Harry films.

Did I Like It: I’d been looking so forward to this one, given the absolutely bananas cast on display, all before they became anything that would be featured above the title. Carrey is here before Ace Ventura: Pet Detective (1994) made him a permanent light in the firmament, and even before Neeson because “that one guy in cool films who isn’t Bruce Campbell” in Darkman (1990). I honestly don’t think I’ve managed to overhype myself on a movie this much since The Flash (2023).

I was really wanting it to be bananas, all the while knowing that I was setting myself up for a goodly amount of disappointment. It never even occurred to me that Carrey is only here in the role of the guy that they find dead in the first few minutes of a Law & Order episode.

There’s probably a reason that both Neeson and Carrey had to wait for another couple of years before they could be considered stars, and it is probably the same reason that Eastwood swore off the prospect of another entry in the series*. This is not the triumphant conclusion one might think of. It’s not oddly funny like The Enforcer (1976), but it might be unreasonable to expect a part five of a series to reach up to the heights of previous entries. The real damning thing here is that Harry may simply not be the hero that the 80s need. Gone are the days where most Americans felt lost amidst a world that was growing too fast for them, and seemed like it had gone completely insane. That’s where Harry thrived: being grumpy but strangely fair among people he would never understand. Now he just seems grumpy.

*He could have gotten away with—and probably be forgiven for—making the main character of Gran Torino (2008) the Unforgiven (1992) for Callahan.

Sudden Impact (1983)

Director: Clint Eastwood

Cast: Clint Eastwood, Sondra Locke, Pat Hingle, Bradford Dillman

Have I Seen it Before: Nope.

Did I Like It: I go into this one not with hype in my head, but a strange amount of comfort with Harry Callahan and his world. What’s more, Eastwood directs here for the only time in the series. Who knows Callahan and his strange mix of gruff recalcitrance and underlying decency better than the man who probably still is largely identified with the role?

And yes, Eastwood is probably most at ease in this film, but that makes the entire film seem distracted. Maybe he was a little too in love with Sandra Locke and decides to spend too much time focusing on her. Plenty of directors, and more than a few stars have fallen victim to the pitfalls of romantic nepotism, but Locke sleep walks through a role that feels like it at least needs to alternate between borderline-catatonic and scene-chewing manic.

Maybe it’s just that this is a down-note entry in the series between The Enforcer (1976) where Eastwood is able to be so relaxed that he actually got to be a bit funny, and The Dead Pool (1988), a weird—purely hypothetical for me at this point—pop cultural amalgamation. It’s entirely possible I’m being too hard on Sudden Impact. A series that goes five films without having any entries that aren’t willfully embarrassing is probably a treasure to behold. Star Trek couldn’t manage that feat. Maybe Dirty Harry is allowed to have an off day.

And now it’s just me and The Dead Pool. I strangely can’t wait. With it’s weird alchemy of Eastwood, Liam Neeson, Jim Carrey (before he started talking out of his ass) and the guys who voices Mario? There’s no possibility this thing will ever live up to the hype I created entirely in my head.

Magnum Force (1973)

Director: Ted Post

Cast: Clint Eastwood, Hal Holbrook, Mitchell Ryan, David Soul

Have I Seen it Before: Never.

Did I Like It: First of all, in my review of Dirty Harry (1971) I noted that since Harry (Eastwood) spent the final moments of that film throwing his badge into the water, the opening minutes of this film pretty much had to have him wading into the water to go retrieve it.

No such luck. By all rights I should get over that little oversight, but thematically it’s a little hard to account for Callahan’s utter—and arguably justifiable—disgust with the system in the context of this movie. Not to spoil the plot of a fifty year old movie, but when it becomes clear that the real bad guys in this film are forces within the San Francisco Police Department*, Callahan has to throw away a quick line about how much he still hates the system, but has to live with it until it changes.

It’s an awkward—and unfortunately load-bearing—moment in an otherwise skillfully constructed thriller. Harry is a hero that I’m increasingly less dubious about headlining a multi-movie franchise. Those shots that are going to be the first up in obituary reels for Eastwood make Callahan seem like the kind of cop one hopes to not meet in a darkened alley, or in bright daylight, or really anywhere. The truth, though, is that Callahan might be a grump, but he is a decent man. He’s not interested in hurting anybody that hasn’t already gone out of their way to hurt other people. He’d even like to gently stop somebody who might hurt somebody from indulging in their worst impulses. He doesn’t kick ass when McCoy (Ryan) starts betraying his meltdown. He tries to talk him into hanging it up before something terrible happens. He doesn’t even sleep with McCoy’s wife, when the runway was absolutely clear. Are all cops bastards? I’ll leave that for other people to decide, but I would at least submit that Dirty Harry Callahan is at least a bastard for the angels.

*An odd paradox in this genre of kick-ass guys with guns starring guys who would be perfectly welcome at the Republican National Convention: They are weirdly, and pointedly, anti-police, or at least eager to admit that police corruption exists and is inherently difficult to route out. I’m surprised that the left haven’t adopted both this film and First Blood (1982) as their own.

Dirty Harry (1971)

Director: Don Siegel

Cast: Clint Eastwood, Andy Robinson, Harry Guardino, John Vernon

Have I Seen It Before: Yes, at some point. Although I’ll admit that I was drawn to the film less for Eastwood’s iconic portrayal of Callahan, and more as an avowed Deep Space Nine fan, I showed up for Andy Robinson’s (Andrew J. Robinson, to his friends) turn as “the killer.”

Is that the most desperately nerdy reason to watch an Eastwood film? It might be, but I also can’t imagine I’m the only one that came to the film that way.

Did I Like It: And there is certainly something to be said for that performance. Robinson is cowardly, dastardly, sniveling, and any other adjective you might use to describe a cartoon heavy, all with still making the Killer always seem as if he is some kind of horrid mutation of a human, but human nonetheless. The pitch-black soul he brings to the film makes a misanthrope like Harry (Eastwood) never seem like he is anything other than the bad guy.

Is Harry Callahan a complete misanthrope? Characters around him certainly seem to think so. But he is kind to his partner and his wife, even though he never really wanted the partner around to begin with. He doesn’t have a chip on his shoulder reflexively, every chip was placed there by someone looking for an easy way out of responsibility. All of that preceding paragraph may start to make one think that I’m somehow going to change my own politics and start talking to empty chairs onstage. Let me assure you, if Harry could get over his own dick for a moment, he might have avoided an honest screw up by putting the heat on the Killer without a search warrant or probable cause, allowing him to be released. Harry is really dumb, but he means well. I offer into evidence his final action in the film, chucking his badge into the water. How does Magnum Force (1973) begin? Him fishing for a badge? Only one way to find out, I suppose.