Clint Eastwood has been a Hollywood icon since he catapulted to stardom with the role of the Man With No Name in Sergio Leone's Dollars trilogy. He quickly became one of the film industry's biggest stars and, in his twilight years, became a director. The A-lister has taken on dozens of projects, boasting one of the most impressive portfolios in cinema history.
Best known for his Western and thriller films, Eastwood has endeared himself to generations of movie fans as a sex symbol and embodiment of the American spirit. However, like many actors, he has had his fair share of flops and box office failures, too. While he rarely makes a bad movie, he still has his fair share that simply failed to resonate with fans the same way Dirty Harry or Unforgiven did. Let's take a look at some of his worst-ranked films throughout his career.

The 1984 film City Heat tells the story of two detectives, Lieutenant Speer (played by Clint Eastwood) and Mike Murphy (Burt Reynolds), in the 1930s. It doesn't take long before the pair get themselves mixed up in Kansas City's organised crime. On one side is a ruthless pit boss; on the other, a mob boss.
With a ledger that documents their criminal activities, they work to bring down the dodgy gangsters, all while pursuing their respective love interests. The film combines slapstick comedy, crime noir, and romance into one 90-minute film, but its confused nature failed to resonate with audiences.
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Moving to a war drama, Lafayette Escadrille tells the story of Thad Walker (Tab Hunter), an American troublemaker who flees the law to join the French Foreign Legion during the First World War. While there, he meets a group of American pilots who form the Lafayette Escadrille and sparks up a romance with a local woman, Renee (Etchika Choureau).
Still defined by his rebellious streak, he soon faces the wrath of the military when he butts heads with a commanding officer, leaving him torn between love and duty. The 1958 film pays homage to the real French squadron and casts Eastwood as one of the young pilots, George Mosley. Unfortunately, despite having a good script and well-formed characters, the film received a mediocre reception from war fans, many of whom claimed it didn't do justice to its inspiration.
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This 1989 rom-com begins when a woman, Lou Ann (Bernadette Peters), steals a car belonging to her husband, Roy, who is a white supremacist, and it doesn't take long before his friends pursue her. After she skis bail, a skip-tracer named Tommy Nowak (Clint Eastwood) is tasked with finding her and puts his expertise into action by going undercover to get close. When he finally tracks her down, he soon falls head over heels for her and eventually helps her escape Roy and rescue her kidnapped baby.
Pink Cadillac should have fit in perfectly with many of Eastwood's previous road trip films, such as Thunderbolt and Lightfoot and Every Which Way But Loose. But when compared with these American classics, the cracks in its portrayal really shine, delivering a very formulaic attempt at the genre.
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The 1956 Western, The First Travelling Saleslady, tells the story of Rose Gillray (Ginger Rogers), a forward-thinking businesswoman in the waning days of the Old West. Despite being a great sales agent, her corset company is on the brink of failure, forcing her to turn to her creditor, Jim Carter, who sets her up selling barbed wire in Kansas. As she works on her sales pitch to ranchers, she earns the affections of Jim and another man, rancher Joel Kingdon (James Arness).
This was one of Eastwood's earliest prominent roles that really helped establish him as the face of the Western genre, albeit in a more lighthearted story than usual. Exploring America's entrepreneurial spirit, progressive change and the dawn of the industrialised 20th century, the film began with a good idea but was let down when it came to the edit.
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