Clint Eastwood’s 10 Worst Movies, Ranked

Acclaimed actor and filmmaker Clint Eastwood has been involved in many extraordinary films, but that is not to say that, throughout his more than 70 years in Hollywood, he has not starred in some awful movies. Eastwood made a name for himself in Westerns such as Sergio Leone’s Dollars Trilogy and as an action star as the title character in the Dirty Harry series. However, he’s also had some unfortunate missteps with out-of-character comedy movies, a Western musical that he has even dismissed, and late-career work that would have played out better when he was a much younger man.

Now in his 90s, Eastwood has been behind terrific movies like Unforgiven, Million Dollar Baby, and Gran Torino, but has also missed the mark with questionable choices as both a star and a director. While these disappointments may not stand as cinematic masterpieces, they are a testament to Eastwood’s willingness to take chances in his career and try new things. Not every project Eastwood has been a part of has been successful, but these lesser films are still an essential part to understanding the unmatched and unique career of Eastwood.

10 Firefox (1982)

Directed by Clint Eastwood

A Cold War thriller directed and starring Clint Eastwood, Firefox was a disappointing adaptation of a novel by Craig Thomas. Based on the extraordinary super fighter plane, the MiG-31 Firefox aircraft, Firefox was a disappointing action movie that, at 137 minutes, overstayed its welcome by at least half an hour. The New York Times film critic Vincent Canby rightfully criticized Eastwood’s lack of control over the plotline and called it “only slightly more suspenseful than it is plausible.” Canby stated: “It’s a James Bond movie without girls, a Superman movie without a sense of humor.”

9 Cry Macho (2021)

Directed by Clint Eastwood

A return to the Western genre, Clint Eastwood was in his 90s when he directed and starred in Cry Macho. The story of a former rodeo star helping a young boy reunite with his father in Mexico, Eastwood playing an old man coming out of retirement worked well in 1992’s Unforgiven, but by this point in his career, Eastwood was about two decades too old to do the story justice. Cry Macho was not terrible, but it recalled the glory days of Eastwood that could never live up to and was a disappointing entry to his often impressive late-career work.

8 Absolute Power (1997)

Directed by Clint Eastwood

With a star-studded cast that included Clint Eastwood and Gene Hackman, Absolute Power, unfortunately, collapsed under the weight of a preposterous plot. A high-octane story including a sexual scandal involving the President of the United States, Absolute Power delivered a few thrills and had an interesting story about a father and daughter reunited after years of estrangement, but all of this was not enough to save it from mediocrity. Absolute Power was a minor entry in Eastwood’s long and varied career, and there are plenty of stronger movies of his to check out before making it to this one.

7 Paint Your Wagon (1969)

Directed by Joshua Logan

A Western musical where Clint Eastwood starred opposite legendary tough-guy character actor Lee Marvin, Paint Your Wagon was released just as movie musicals were going out of fashion and at 154 minutes felt like it had an overlong and unjustified runtime. Eastwood and Marvin played their parts well in a story about two prospector partners in a gold mining town who share the same wife, played by Jean Seberg, but it just never quite captured the energy and excitement needed to make a film like this work. Eastwood notoriously hated Paint Your Wagon, and it was his first and last foray into the world of movie musicals.

6 The Dead Pool (1988)

Directed by Buddy Van Horn

While The Dead Pool may contain one of Clint Eastwood’s best movie quotes about opinions and how everybody has one, that was not enough to save this disappointing film. The final and weakest entry in the Dirty Harry series, it appeared as if Eastwood realized this character had run its course and, after its release, decided to retire the no-nonsense inspector for good. While discussions about bringing the character back do flair up from time to time, Eastwood had no interest in revisiting Dirty Harry since The Dead Pool and stated that he was now too old (via Irish Examiner.)

5 Every Which Way But Loose (1978)

Directed by James Fargo

The pairing of Clint Eastwood with an orangutan in an offbeat comedy at first appeared like a strange fever dream, until the realization that it was a real movie called Every Which Way But Loose. This uncharacteristically light role highlighted Eastwood’s faults as a comedy actor and shockingly led to a sequel that created Eastwood’s worst franchise in a career filled with triumphs. The most shocking part about Every Which Way But Loose was that it remains Eastwood’s biggest film as its PG rating allowed the whole family to enjoy this paring of man and monkey.

4 The Rookie (1990)

Directed by Clint Eastwood

A buddy action film, The Rookie featured Clint Eastwood teaming up with a young detective played by Charlie Sheen in a disappointing, overbudgeted, action disaster that wasted the power of its talented cast and crew. Unfortunately, the two stars don’t have much chemistry and The Rookie felt like it was more a reaction to the success of films like Die Hard and Lethal Weapon than a genuine passion project for Eastwood. Film critic Roger Ebert stated that the movie was “jammed with material and the budget was obviously large” but that despite everything on the screen, it remained “lifeless.”

3 Pink Cadillac (1989)

Directed by Buddy Van Horn

The third and final collaboration between Eastwood and Buddy Van Horn, Pink Cadillac ended their partnership on a sour note with an action comedy that left a lot to be desired. A box office bomb, the failure of Pink Cadillac inspired Eastwood to move away from the action comedy genre and just three years later he would find himself as the director and star of the Academy Award for Best Picture winner Unforgiven. This leap was a far cry from the lazy comedy of Pink Cadillac.

2 City Heat (1984)

Directed by Richard Benjamin

The pairing of Clint Eastwood and Burt Reynolds should have been a major box office hit, but City Heat, which featured the two as two law enforcers investigating a murder, took in a modest $38 million on a budget of $25 million (via Box Office Mojo.). The star power of its leads was not enough to save the film from failure and Reynolds stated he knew during filming the movie would fail. “It’s regrettable the material wasn’t there because Hollywood or maybe just Warner Bros. will never let Clint and I act together again,” Reynolds said (via Los Angeles Times.)

1 Any Which Way You Can (1980)

Directed by Buddy Van Horn

The sequel to Every Which Way But Loose, Any Which Way You Can once again paired Clint Eastwood with his orangutan friend Clyde, who had even more screen time than in the predecessor, for a series of misadventures involving the mob, cops, and motorcycle gangs. As Eastwood’s lowest-rated film on Rotten Tomatoes, with a meager 20%, Any Which Way You Can had an illogical plot and was a low point in the acclaimed career of Clint Eastwood. Despite this, Any Which Way You Can found success at the box office and made $70 million on a budget of $15 (via Box Office Mojo), so critical acclaim may not be everything.

Sources: New York Times, Irish Examiner, Roger Ebert, Box Office Mojo, Rotten Tomatoes, Box Office Mojo