The 8 Clint Eastwood Movies That Defined His Career

Established actor and director Clint Eastwood is remembered for his highly decorated career, starring in some of the best Western movies of all time. Since the beginning of Eastwood’s career in 1955, he’s starred in over 60 film titles as an actor and has directed over 40, which is an impressive feat across an almost seven-decade span. Along the way, certain movies helped cement his legacy and define his on-screen persona.

Of course, with such a brilliant and diverse list of films under his belt, it’s difficult to identify which Clint Eastwood movies are the best. However, there are clear titles that stand out in Eastwood’s backlog of cinematic masterpieces, whether that be for a stellar performance, beautiful direction, or both. With so many films to enjoy, it’s worth considering just which of Clint Eastwood’s projects stand out as defining moments in his career.

1
A Fistful of Dollars (1964)

Eastwood’s Breakthrough Role

While Eastwood had several uncredited performances in films in the late 1950s, his breakthrough film role came in 1964’s A Fistful of Dollars, the first in Sergio Leone’s Dollars trilogy. A Fistful of Dollars quickly established the connection between Eastwood and Spaghetti Western films, famously portraying the Man with No Name. It also allowed Eastwood to make the jump from TV to movies, having previously made a name for himself in the Western TV series Rawhide.

Despite the Man with No Name having limited dialogue, Eastwood’s use of body language and facial expressions helped secure the future of the franchise. A Fistful of Dollars also marked the beginning of Eastwood’s collaborations with Sergio Leone, which helped ensure his evergrowing popularity in the Western genre. With themes of justice and revenge, A Fistful of Dollars not only setup Eastwood’s career, but launched him into superstardom.

2
Paint Your Wagon (1969)

Eastwood’s Attempt At Being A Song And Dance Man

1969’s Paint Your Wagon saw Eastwood in the only musical in his career, and despite not being a singer in the traditional sense, he recorded the vocals for his character’s tracks. Paint Your Wagon didn’t see much success, at least upon its initial release. This was mainly because, at this point in time, musicals were going out of fashion in the film industry, and this problem was one of the reasons why Eastwood was so keen to start directing himself.

Despite this, Paint Your Wagon still managed to clinch a Golden Globe nomination for Best Motion Picture in 1970. Eastwood’s performance as Pardner was praised because of how he effortlessly broke out of the stoic archetype of characters he’d become known for. While Paint Your Wagon isn’t one of his best roles or movies, it is remembered as one of Eastwood’s more versatile on-screen appearances.

3
Kelly’s Heroes (1970)

From The Saloon To The Trenches

The 1970 film Kelly’s Heroes saw Eastwood’s versatility as an actor, swapping out his typecast roles as a cowboy to play the war-trodden Private Kelly. The war comedy movie was very different for Eastwood, but it helped expand his portfolio as a performer, attracting unintentional, yet positive, attention for the film. Over 50 years since its release, Kelly’s Hero still stands as a cult classic, especially for Eastwood’s humourous yet stern characterization.

Kelly’s Heroes also marked Eastwood’s first collaboration with director Brian G. Hutton. Eastwood’s work on Kelly’s Heroes with Hutton was clearly successful, which also helped set up future projects for the two, such as 1968’s Where Eagles Dare. While Private Kelly wasn’t a typical role for Eastwood, Kelly’s Heroes is a defining staple in his career and introduced a more diverse, flexible actor to the film industry.

4
Dirty Harry (1971)

Being Harry Callahan Definitely Made Eastwood’s Day

One of Clint Eastwood’s most legendary films was 1971’s Dirty Harry, with the actor portraying the no-nonsense Detective Harry Callahan. Well remembered for its impact on popular culture, Dirty Harry had many iconic quotes, such as “‘Do I feel lucky?’ Well, do ya, punk?” and “I know what you’re thinking. ‘Did he fire six shots or only five?’“ Eastwood’s portrayal of Callahan was praised for his antihero persona and how he demonstrated the character’s ambiguous morals, quickly becoming one of his most recognizable roles.

In fact, Eastwood was so popular as Callahan that Dirty Harry spawned into several sequels: 1973’s Magnum Force, 1976’s The Enforcer, 1983’s Sudden Impact, and 1988’s The Dead Pool. Considering the success that Eastwood saw as Callahan, plus the commercial success of the film, it’s no surprise that Dirty Harry stands out in Eastwood’s filmography.

5
Play Misty for Me (1971)

Eastwood’s First Stint As A Director

Play Misty for Me was a staple moment in Clint Eastwood’s career, making his directorial debut with the 1971 film. Steering away from his usual genre, Play Misty for Me also saw Eastwood playing a radio disk jockey being obsessively stalked by Evelyn (Jessica Walter) in the fascinatingly endearing psychological thriller. Interestingly, Play Misty for Me was shot in Carmel-by-the-Sea, California, where Eastwood would eventually become the Mayor of, from 1986 to 1988.

Having to work both in front and behind the camera posed a new challenge for Eastwood, one that he took to very well. For a first-time director, Play Misty for Me was an incredible debut for Eastwood, receiving critical acclaim. Play Misty for Me not only saw Eastwood continue proving just how versatile a performer he is, but it also cemented him as a double threat in Hollywood as both a director and actor.

6
The Outlaw Josey Wales (1976)

Western’s Biggest Star Changed Up The Genre

The Outlaw Josey Wales was another film Eastwood’s second attempt at directing, but it is mainly remembered for his twist on the typical Western genre. Adapted from the Asa Earl Carter novel The Rebel Outlaw: Josey Wales, Eastwood’s directional choices were praised for many reasons, but most importantly, because of how he took tropes from the Western genre and flipped them. The Outlaw Josey Wales threw the stereotypical portrayals of Western characters away and redefined them, especially with Lone Watie (Chief Dan George) and Little Moonlight (Geraldine Keams), both of whom came from a Native American background.

7
Every Which Way but Loose (1978)

Clint Eastwood Means (Monkey) Business

1978’s Every Which Way but Loose saw Eastwood starring as fighter Philo Beddoe in a strange, yet hysterical, action comedy film. The film is best remembered for Eastwood’s weird choice in costar, an orangutan. While Every Which Way but Loose was a great way for Eastwood to show off his sense of humor, it also had its deeply emotional moments, with Eastwood once again proving just how universal an actor he is. Despite its almost parodical tone, Every Which Way but Loose is one of Eastwood’s highest-grossing films, along with its 1980 sequel, Any Which Way You Can.

8
The Bridges of Madison County (1995)

Eastwood’s Take On A Love Story

The Bridges of Madison County, an adaptation of the Robert James Waller novel of the same name, saw Eastwood delve into the romance genre. Clint Eastwood directed and starred in the project opposite Hollywood legend Meryl Streep, with the two portraying the complicated marriage between their two characters beautifully. While romance isn’t a typical area for Eastwood to work in, The Bridges of Madison County received widespread critical acclaim. If he’d decided to go in another direction, Streep would unlikely have received her nomination for the Academy Award for Best Actress in 1996.

9
Million Dollar Baby (2004)

How Boxing Stormed The Oscars

Million Dollar Baby is a huge staple in Eastwood’s career for several reasons. Of course, Million Dollar Baby once again sees Eastwood dipping his toes into a different genre, this time being a sports drama, something very different from his usual work. However, Million Dollar Baby is one of Clint Eastwood’s most decorated films. Following its release in 2004, Million Dollar Baby received an incredible seven Oscar nominations, including Best Picture and Best Director. Amazingly, the film was so popular that it had a six-month cinema run, an impressive achievement compared to the average length of one month.