Clint Eastwood's Most Disappointing Movie Roles

City Heat (1984)

The 1984 film 'City Heat' directed by Richard Benjamin, featured a pairing of Clint Eastwood and Burt Reynolds as two law enforcers investigating a murder. Despite the star power of its leads, the film failed to impress at the box office, taking in a modest $38 million on a budget of $25 million. Reynolds even expressed regret, stating that the material wasn't there, and he knew during filming that the movie would fail.

Clint Eastwood talking to Burt Reynolds in City Heat

Absolute Power (1997)

Directed by Clint Eastwood and featuring a star-studded cast, 'Absolute Power' unfortunately collapsed under the weight of a preposterous plot. The high-octane story, including a sexual scandal involving the President of the United States, delivered a few thrills but was not enough to save it from mediocrity. Despite being a minor entry in Eastwood’s career, it failed to leave a lasting impression.

Clint Eastwood and Ed Harris in Absolute Power

The Dead Pool (1988)

The final and weakest entry in the Dirty Harry series, 'The Dead Pool' may contain one of Clint Eastwood’s best movie quotes, but that was not enough to save this disappointing film. It appeared as if Eastwood realized this character had run its course and decided to retire the no-nonsense inspector for good. This film marked a low point in Eastwood's impressive career.

Clint Eastwood wearing sunglasses as Dirty Harry in The Dead Pool (1988)

Pink Cadillac (1989)

The action comedy 'Pink Cadillac' ended the partnership between Eastwood and Buddy Van Horn on a sour note. A box office bomb, the failure of Pink Cadillac inspired Eastwood to move away from the action comedy genre. This film marked a turning point in Eastwood's career, leading him to take on more serious and critically acclaimed projects.

Clint Eastwood and Bernadette Peters in Pink Cadillac

Paint Your Wagon (1969)

'Paint Your Wagon' was a Western musical that marked Eastwood's first and last foray into the world of movie musicals. Released just as movie musicals were going out of fashion, it felt like it had an overlong and unjustified runtime. Eastwood notoriously hated the film, and it failed to capture the energy and excitement needed to make a film like this work.

Clint Eastwood Paint Your Wagon

Every Which Way But Loose (1978)

The pairing of Clint Eastwood with an orangutan in an offbeat comedy led to 'Every Which Way But Loose,' a film that highlighted Eastwood’s faults as a comedy actor. This uncharacteristically light role shocked audiences and led to a sequel that created Eastwood’s worst franchise in a career filled with triumphs.

Clint Eastwood and Clyde in Every Which Way But Loose

The Rookie (1990)

The disappointing buddy action film 'The Rookie' featured Clint Eastwood teaming up with a young detective played by Charlie Sheen. Despite the talented cast and crew, the film felt like a reaction to the success of other action films and lacked the chemistry needed to make it a success.

Clint Eastwood with a gun in The Rookie

Any Which Way You Can (1980)

The sequel to 'Every Which Way But Loose,' 'Any Which Way You Can' once again paired Clint Eastwood with his orangutan friend Clyde, for a series of misadventures. Despite finding success at the box office, it marked a low point in Eastwood's career, with its illogical plot and lack of critical acclaim.

Any Which Way You Can (1980) Clint Eastwood and Clyde

Cry Macho (2021)

In 'Cry Macho,' Eastwood played an old man coming out of retirement, a role that worked well in his earlier film 'Unforgiven.' However, by this point in his career, Eastwood was about two decades too old to do the story justice. While the film was not terrible, it was a disappointing entry to his often impressive late-career work.

Clint Eastwood and the Cry Macho poster