Favorite Clint Eastwood Films

In recent years, I’ve abandoned Clint Eastwood. Unable to connect with most of his films and his politics, which he hasn’t hidden.

I took a chance on The Mule (2019), but played it safe and watched the DVD. I found it entertaining though hardly a great film. These days, I’ll settle for entertaining.

Eastwood has quite a film legacy over his seven decades of work. For fun, I looked for ten of his films I enjoy the most. This is not a “best” list, just my personal favorites.

Kelly’s Heroes (1970)

Is this a war film or a heist film? It’s both. Is it a drama or a comedy? It’s both. Eastwood was the big star but it’s an ensemble film, he was an actor-for-hire here. Bob Newhart and Don Rickles co-star, that should tell you this is not Patton or The Battle of the Bulge. There are lots of spectacular explosions and action to give it great visual appeal. It’s a fun film, but I believe it could have been shorter and more tightly edited.

Dirty Harry (1971)

This is the film that turned Eastwood from A-List actor to superstar and cultural icon. According various accounts, the film was offered to John Wayne, Burt Lancaster, Steve McQueen and Paul Newman, who suggested Eastwood. During development, Frank Sinatra was attached to the film, originally written as a character in his 50s. Eastwood agreed and jettisoned most of the drafts to get closer to the script by Harry Julian Fink and Rita M. Fink. The politics of the film and aggressive violence of Harry Callahan caused the script and film rights to change hands many times. The violence, not so much the graphic nature, rather the police use of it, changed cop films forever. The film’s style and music established the loner vibe of Callahan and moodiness that was a part of Eastwood’s 1970s films.

Magnum Force (1973)

The first sequel to Dirty Harry and the best sequel. This film in several ways was better than the original, it’s more stylistic and the Harry Callahan character is better written. This film softened Callahan, it was the rookie cops who were the vigilantes, and a scene was written to show him with a love life, added at the request of female fans. As usual, the supporting cast is wonderful with Mitchell Ryan, Hal Holbrook, David Soul, Tim Matheson, Robert Urich, Kip Niven, Albert Popwell and Felton Perry. John Milius and Michael Cimino wrote the screenplay, with veteran director Ted Post at the helm, although he and Eastwood reportedly clashed about many scenes.

High Plains Drifter (1973)

My favorite Eastwood Western. This is not your typical Western, which makes it fun and pleasing. Eastwood squints and grunts, and his character is so mysterious he doesn’t have a name. The town he saves from vengeful outlaws, reluctantly gives in to his demands but has no lasting allegiance to him. The old-ball characters in the film are delightful and Eastwood’s directing touch makes this an edgy film. Eastwood learned early to hire good supporting actors and let them put their thing down.

Thunderbolt and Lightfoot (1974)

One of Eastwood’s few films that he didn’t direct. This was a bit of a departure for Eastwood. Not a cop or a Western, but he does play a criminal, although a retired one hiding out as a preacher. Written and directed by Michael Cimino (The Deer Hunter), this is an ensemble film that has a toughness but also a lighter tone. Jeff Bridges, George Kennedy and Geoffrey Lewis make up Eastwood’s crew. Eastwood squints but also smiles. Very engaging film.

Tightrope (1984)

Although his box office didn’t always say this, Eastwood’s career was in a slump as he was aging. He was still a heavyweight, but he was trying to remain relevant to a more youthful audience. This film had him playing another cop, but not the same kind of cop. Written and directed by Richard Tuggle, Eastwood’s cop was an integral part of the story and hinted that he might be a suspect in some kinky murders. Of course he wasn’t the killer, but the psychological aspects had his character off-balance. This would rank as one of his better 1980s films, in a decade in which he made money, except for his very personal films. He hopped from genre to genre, seemingly with equal success, but this was a filmmaker trying to stay on the top of the heap. I found this a decade difficult to embrace his films.

Heartbreak Ridge (1986)

This was a pretty goofy film. Based around the U.S. invasion of Grenada, it’s a story of a burnt-out Marine Sergeant taking over a poorly trained and disciplined squad of soldiers, and reconnecting with his ex-wife. For me, a high-point for his 1980s career, it utilizes Eastwood’s age and crustiness. The story is slight and the direction nothing special, but it doesn’t aim too high. This is really a character-film, not an action film, and Eastwood stocks the story with oddball characters. This is somewhere between Full Metal Jacket and Gomer Pyle, USMC.

Midnight in the Garden of Good and Evil (1997)

The only film on my list he directed but didn’t star in. Personally, I think later in his career he’s generally a better director of films he doesn’t act in. The source material had great spice and style. Eastwood’s challenge was in capturing the mood and textures, casting, and not being too heavy-handed. He accomplished all three. His choice of actors, in both lead and support roles was on the money, and John Cusick turned in a performance worthy of Jack Lemmon or Jimmy Stewart, affable and someone characters warmed up to and trusted.

Space Cowboys (2000)

Much like Heartbreak Ridge in style, this is really more of a character film than a space-action film. Eastwood, Donald Sutherland, Tommy Lee Jones and James Garner have a ball as a group of original astronauts whose mission was scrapped and now have their chance as old geezers to have their moment. Eastwood gives the best moments to his other actors. His direction is very good, this is a big budget production, with big expectations. This is improbable but engaging film, and it’s fun.

Gran Torino (2008)

Hard to believe this was made 11 years ago. I thought maybe it would have been Eastwood’s last starring role, but it wasn’t. Eastwood’s more recent starring roles walk a fine line between realism and sentimentality. I found a lot of similarities between this film and The Mule, which didn’t get the notice or box office that Gran Torino did. Older Eastwood characters are worn and vulnerable, and looking for some measure of redemption.

You’ll notice some good films missing from the list: The Sergio Leone Westerns, Play Misty For Me, The Bridges of Madison County, Undefeated, his Iwo Jima films, Million Dollar Baby, The Outlaw Josey Wales, The Enforcer, Mystic River and In the Line of Fire. Nothing wrong with any of these films. The Bridges of Madison County would be on my list if I picked 11 films, and Breezy, a film he directed but didn’t act, if the list was a dozen.

One thought on “Favorite Clint Eastwood Films

  1. I dislike Eastwood’s right-wing politics, too, and consider him a stiff actor. But he has definite “presence” and has starred in some great films. My fave of his – in fact, it may be in my top two of all time – is the spaghetti The Good, the Bad, and the Ugly. Sergio Leone, Eli Wallach, and Lee Van Cleef helped catapult that one.


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