7 Clint Eastwood Movies Even He Regrets Making, Ranked Worst to Best

Clint Eastwood has made a name as a prolific actor and filmmaker in Hollywood. He has directed 40 films over his more than 6-decade career and has experimented with various genres. While he is known for Westerns, he has made war dramas, action blockbusters, true-crime thrillers, and even a musical.

However, Eastwood is a hit-or-miss filmmaker, with many of his films falling short of their ambition. Even as just an actor, he has made a few questionable career choices and contributed to some career setbacks. Here are seven films from his filmography that even he expressed regret for.

7 The 15:17 To Paris

Clint Eastwood chose to experiment with his 2018 real-life drama The 15:17 To Paris by casting the real-life heroes who squashed the terrorist attack depicted in the movie. The main cast, Spencer Stone, Alek Skarlatos, and Anthony Sandler, were not professional actors. It was a gamble that ultimately did not pay off and caused Eastwood to regret.

Movie Name	Rotten Tomatoes (as of April 26, 2026)	IMDb (as of April 26, 2026)	Streaming/Rent
The 15:17 to Paris	24%	5.3	Amazon Prime Video

Despite some thrilling elements in the film, most criticized the actors’ lack of experience and chemistry, bringing down the drama of the film. The film was still a hit, earning $57 million at the box office (via Box Office Mojo).

6 City Heat

The crime comedy City Heat had a noted star cast, with Burt Reynolds and Clint Eastwood joining hands along with Mary Alexander and Rip Torn. The buddy comedy, however, was not well-received, with Roger Ebert thrashing the film for its lack of awareness with its treatment and almost termed it a parody (via Roger Ebert).

Movie Name	Rotten Tomatoes (as of April 26, 2026)	IMDb (as of April 26, 2026)	Streaming/Rent
City Heat	22%	5.5	Apple TV

The films of the ‘80s marked a stark shift in Eastwood’s career, with films like City Heat and The Rookie encouraging him to move towards themes that were explored in Unforgiven. City Heat was also regretful for Burt Reynolds, as a painful stunt affected his life adversely.

5 Jersey Boys

Clint Eastwood and a musical are an unlikely combo, but the actor had deep ties with music. Eastwood has produced several albums, has expressed his love for jazz, and has composed scores for his movies like Mystic River and Million Dollar Baby. However, everyone’s fears came true when he took over the reins of Jersey Boys, based on the hit jukebox musical of the same name.

Movie Name	Rotten Tomatoes (as of April 26, 2026)	IMDb (as of April 26, 2026)	Streaming/Rent
Jersey Boys	51%	6.8	Amazon Prime Video

Eastwood’s adaptation deviated slightly from the Broadway show and lost much of its flair as the filmmaker gave it a realistic treatment. While Christopher Walken’s performance was appreciated, many criticized Eastwood’s direction (via Daily Express). Frankie Valli, the original member of The Four Seasons, also agreed that Eastwood was a wrong choice.

4 Paint Your Wagon

Another Clint Eastwood musical that turned out to be regretful for the actor was Paint Your Wagon. It also combined his most prevalent genre, the Western. Eastwood has explicitly stated that he regrets the film, especially his singing in the movie.

Movie Name	Rotten Tomatoes (as of April 26, 2026)	IMDb (as of April 26, 2026)	Streaming/Rent
Paint Your Wagon	45%	6.6	Amazon Prime Video

He said (via Far Out Magazine),

I was crazy enough to try anything. I’ve always been interested in music; my father was a singer, and I had some knowledge of it. Although what I was doing in that picture was not singing.

The film also starred Lee Marvin and Jean Seberg, along with John Mitchum.

3 Sudden Impact

The Dirty Harry franchise turned Clint Eastwood into an A-list star. Multiple sequels were made, including Sudden Impact, which the actor directed himself. While it was a blockbuster like other films in the Magnum Force franchise, Eastwood seemed to regret the film and expressed that he should not have made it.

Movie Name	Rotten Tomatoes (as of April 26, 2026)	IMDb (as of April 26, 2026)	Streaming/Rent
Sudden Impact	52%	6.6	Amazon Prime Video

Eastwood claimed that he directed it because he wanted to helm one film in the series before ending it, and that was the only reason. He said (via Comic Basics),

I thought the first Dirty Harry was a terrific film, and it was always going to be hard to follow that. But it was almost like saying, ‘I’m the only one who hasn’t directed a Dirty Harry movie, so I might as well do one.’

The film was not the last in the franchise, and Eastwood came back as an actor for the film The Dead Pool.

2 The Beguiled

While 1971 marked the beginning of the Dirty Harry series with Clint Eastwood and director Don Siegel, the duo collaborated before in the same year with the drama The Beguiled. Eastwood played a Union soldier injured and taking shelter in a girls’ school. The tale of desire and faith received good reviews, but Eastwood was not happy.

Movie Name	Rotten Tomatoes (as of April 26, 2026)	IMDb (as of April 26, 2026)	Streaming/Rent
The Beguiled	90%	7.1	Amazon Prime Video

The actor mentioned that the film’s box office response is what made him regret it and said he failed the film (via The Mirror).

The one picture I failed in was The Beguiled…It was good for me personally, critically well-received, but it was very poor for the company that spent the money to produce it. Maybe it couldn’t have been successful because the hero failed…He tried to do everything through the back door. He wasn’t such a bad person; he was just trying to exist.

The film was a flop, earning only $1.1 million at the box office (via Box Office Mojo).

1 The Eiger Sanction

Clint Eastwood never got to play James Bond, but he got his desire fulfilled with the action thriller The Eiger Sanction. One of his earlier films as a director, the film was ambitious, where Eastwood chose to shoot at the real Eiger Mountains and saw him risk his life for the climbing sequences.

Movie Name	Rotten Tomatoes (as of April 26, 2026)	IMDb (as of April 26, 2026)	Streaming/Rent
The Eiger Sanction	64%	6.4	Amazon Prime Video

However, the consequence of doing real-life stunts is the risk, where Eastwood himself went through an accident, and a crew member died in a separate incident. Eastwood said (via Slash Film).

That was a psychologically damaging thing to do. You do it, and for three days afterward, you’re just staring off. You don’t say much.

The film had a decent run at the box office, earning only $14 million (via Box Office Mojo). But fans have praised it for its visceral action sequences.

Movie Name	Rotten Tomatoes	IMDb	Streaming/Rent
The Eiger Sanction	64	6.4	Amazon Prime Video
The Beguiled	90	7.1	Amazon Prime Video
Sudden Impact	52	6.6	Amazon Prime Video
Paint Your Wagon	45	6.6	Amazon Prime Video
Jersey Boys	51	6.8	Amazon Prime Video
City Heat	22	5.5	Apple TV
The 15:17 to Paris	25	5.3	Amazon Prime Video

Which do you think is Clint Eastwood’s most regrettable film? Comment below.