Clint Eastwood has had an amazing career in Hollywood, starting as a western actor on TV and in the movies before moving on to a very successful crime police drama franchise with Dirty Harry. Along the way, Eastwood also shined in some Italian spaghetti western before finally moving behind the camera.
With the movie Unforgiven, Eastwood proved that he was more than a genre actor and was one of the best directors in the world. His later films have been a bit polarizing, but Eastwood still possesses a great eye for direction and can still steal a scene as an actor. Here is a look at Clint Eastwood’s five best and five worst movies, based on Rotten Tomatoes.
10. WORST: CITY HEAT (1984) – 19%
Released in 1984, Clint Eastwood teamed up with fellow icon Burt Reynolds for City Heat. Eastwood is Lt. Speer, a by-the-book cop who teams with his old friend Mike Murphy (Reynolds), who is now a private eye. The entire lure of this movie is the two film-screen icons playing off each other.
Critics pointed to a last-minute change in director to create a film without charm, no thrills, but a great cast. Neither critics (19% rotten) nor fans (23% rotten) liked this Clint Eastwood movie.
9. BEST: UNFORGIVEN (1992) – 96%
In 1992, Clint Eastwood directed his 16th movie, which might come as a shock to many fans. However, it was that 16th film that was his masterpiece. Unforgiven was a deconstruction of the western genre, with Eastwood as a retired outlaw living peacefully in a town with corrupt Sherrif Little Bill Daggett masterfully portrayed by Gene Hackman
Add in the amazing Morgan Freeman as Ned Logan and Eastwood created what many consider the last great western. The film won the Academy Award for Best Picture, and Eastwood brought home the award for Best Director.
8. WORST: ANY WHICH WAY YOU CAN (1980) – 20%
Clint Eastwood found his lowbrow crowd-pleaser with Any Which Way But Loose in 1978. That movie saw Eastwood as a bare-knuckle boxer who was often upstaged by his orangutan Clyde. Critics didn’t like it much, but fans on Rotten Tomatoes gave it a 56% fresh rating.
However, the sequel in 1980, Any Which Way You Can, fell hard with both critics and fans. The movie has Eastwood’s Philo wanting to head back to the ring to fight again, while Clyde once again steals the show. In this case, both critics (20%) and fans (45%) gave the movie a thumb’s down.
7. BEST: HIGH PLAINS DRIFTER (1973) – 96%
Clint Eastwood’s second directorial effort was High Plains Drifter, which he starred in as well. The 1973 movie was not part of the Man with No Name trilogy, but the character was as close as you can get. Eastwood played an unnamed drifter known only as The Stranger, who rode into town and dealt out justice.
It was clear that Eastwood learned a lot from his mentors in Sergio Leone and Don Siegel. Critics praised the movie, calling it comical, stylish, mysterious, and wholly satisfying. It ended up with a 96% fresh rating.
6. WORST: PINK CADILLAC (1989) – 21%
Released in 1989, Pink Cadillac starred Clint Eastwood as Tommy, a skip-tracer who is after the wife of a member of a white supremacist group who happened to run off with their counterfeit money. She is out on bail and skipped out, putting Tommy on her tail.
When the white supremacist group threatens her baby, Tommy decides to help her instead of taking her in. Ranked at 21% rotten by critics and 25% rotten by fans, the film was called lazy, dull-witted, and overlong.
5. BEST: ESCAPE FROM ALCATRAZ (1979) – 96%
Directed by Don Siegel, Escape from Alcatraz starred Clint Eastwood as Frank Morris, a brilliant prisoner who has escaped from several facilities and ended up at the unescapable Alcatraz. The film then tells the story of the inmates, their relationships, and the eventual success of their impossible escape from Alcatraz.
Critics loved the movie, giving it a high 96% fresh rating calling it one of the best prison movies ever made. Fans were on board as well, with an 85% fresh rating.
4. WORST: THE 15:17 TO PARIS (2018) – 23%
When it comes to The 15:17 to Paris, this is the lowest-rated movie Clint Eastwood directed based on Rotten Tomatoes. Both critics (23%) and fans (38%) discounted the movie, which was considered a well-intentioned movie that fell apart due to Eastwood casting the real heroes as the film’s leads.
It was an interesting take, as Eastwood thought he could honor the heroes by letting them tell their own story, but these are not actors, and the movie stumbled due to their inexperience and the fact that most of the film did not do their story justice.
3. BEST: THE GOOD, THE BAD, AND THE UGLY (1966) – 97%
It should come as no shock that the two best movies of Clint Eastwood’s career were both from the Man with No Name trilogy. What might be a little surprising is that The Good, The Bad, and The Ugly is the second-best of the films.
Released in 1966 by director Sergio Leone, this was the final movie in the trilogy and is best-known for the standoff scene between Clint Eastwood, Lee Van Cleef, and Eli Wallach. The film saw both critics and fans give it an identical 97% fresh rating, crediting its breathtaking landscapes, compelling story, and memorable performances.
2. WORST: PAINT YOUR WAGON (1969) – 27%
Paint Your Wagon starred Clint Eastwood as a man named Pardner and was a musical western released in 1969. Based on the 1951 Broadway play, Lee Marvin starred as Ben, a prospector, with Eastwood as his companion. When Ben buys a woman from a Mormon, she demands equal rights and lives with the two men.
The fans and critics were split on this, with critics deeming it rotten at 27% while fans liked it better, with a higher 68% rating. With both Eastwood and Marvin singing, the critics called it a flop with nothing going on.
1. BEST: A FISTFUL OF DOLLARS (1964) – 98%
The best Clint Eastwood movie of all-time, according to Rotten Tomatoes, came in 1964 and was the first film in the Sergio Leone Man with No Name spaghetti western trilogy. A Fistful of Dollars was a slight remake of Akira Kurosawa’s Yojimbo, but added the Old West as the template and became something much bigger.
Eastwood plays the unnamed gunfighter who comes to town and offers his help to two rival gangs, neither aware he is playing both sides. With a 98% critical freshness rating at Rotten Tomatoes, it remains Clint Eastwood’s defining role.