1. Unforgiven (1992)

IMDB rating: 8.2/10
Rotten Tomatoes rating: 96%

Storyline:
Unforgiven is a Western film directed by Clint Eastwood himself, presenting an unvarnished and bleak view of the violent frontier. Eastwood stars as William Munny, a former outlaw and murderer who left his life of crime behind to raise his two children. When a bounty is announced on a couple of criminals who scarred a prostitute, Munny picks up his guns one last time, along with his old friend Ned Logan and a cocky young gunslinger, The Schofield Kid.

Why it’s a major performance:
Unforgiven is considered a landmark in the Western genre, offering a deconstruction of many of the traditional tropes and themes. Eastwood’s portrayal of William Munny is a masterclass in nuanced performance, with his weathered face and gruff demeanor imbued with the weight of a violent past and simmering sense of morality. This character is one of the most complex and morally ambiguous ones in the entire Eastwood repertoire and perhaps in all of Western cinema.

In addition to that, Unforgiven brought a fresh and more realistic outlook on the violent Old West and earned Eastwood his first Oscars for Best Director and Best Picture. The film’s desolate atmosphere and complex characterization mark a departure from his earlier, more traditional Westerns, underscoring Eastwood’s growth and maturity as an artist.

2. The Good, the Bad, and the Ugly (1966)

IMDB rating: 8.8/10
Rotten Tomatoes rating: 97%

Storyline:
Set during the American Civil War, The Good, the Bad, and the Ugly plots three gunslingers vying for a fortune in Confederate gold. Eastwood stars as “Blondie” (the Good), who forms an uneasy alliance with Tuco (the Ugly), a Mexican bandit, to outwit their nemesis Angel Eyes (the Bad), a cruel and ruthless mercenary.

Why it’s a major performance:
Directed by Sergio Leone and scored by Ennio Morricone, the film showcases Eastwood’s magnetism and charisma as the enigmatic, stoic Man with No Name, carrying the mantle of the traditional Western hero but attributing it with an air of mystery, callousness, and aloof charm. It is this role that solidified Eastwood’s status as a Western icon.

Besides, Eastwood’s performance in The Good, the Bad, and the Ugly allowed him to break away from the clean-cut Hollywood archetype and affirmed his mastery of the Spaghetti Western genre. His character displays a unique blend of gallantry and ruthlessness which truly sets him apart, marking a high point in his acting career.

3. Million Dollar Baby (2004)

IMDB rating: 8.1/10
Rotten Tomatoes rating: 91%

Storyline:
Clint Eastwood directs and stars in Million Dollar Baby, a drama about an aspiring female boxer, Margaret “Maggie” Fitzgerald (played by Hilary Swank), who is trained by an old, grizzled boxing coach, Frankie Dunn (Eastwood).

Why it’s a major performance:
Eastwood’s performance as Frankie Dunn, the hardened, introspective boxing trainer, presents another facet to his multifaceted career. His portrayal of Frankie is a masterful study in subtlety and restraint, generating much of the film’s emotional heft, for which he received an Academy Award nomination for Best Actor.

Moreover, Million Dollar Baby has Eastwood embodying the universal figure of the tough-love mentor, his character serving as a counterpoint to Swank’s eager and tenacious Maggie. With this film, Eastwood manages to peel back the layers of the worn-down and weary trainer, demonstrating a vulnerability and emotional depth that left an indelible impression on both audiences and critics alike.

4. Dirty Harry (1971)

IMDB rating: 7.8/10
Rotten Tomatoes rating: 91%

Storyline:
Eastwood steps into the role of the iconic, hard-boiled detective “Dirty” Harry Callahan in a quest to apprehend a psychopathic killer known as the Scorpio. With his unconventional methods and defiant attitude towards bureaucracy, Harry leaves a trail of shattered rules and regulations in his pursuit of justice.

Why it’s a major performance:
Dirty Harry marked Eastwood’s move away from Westerns into the gritty urban landscape, and it was here that he brought forth a new kind of hero – one that was willing to bend and break the law to see justice done. His performance established Harry Callahan as a pop culture icon and led to multiple sequels, with Eastwood’s dialogue becoming instantly recognizable.

Further, Eastwood’s cold, steely portrayal of the lone-wolf cop showcased his capacity to infuse his characters with just enough humanity to make them relatable, whilst also maintaining their larger-than-life aura. This balanced act, combined with the film’s enduring cult status, cements Dirty Harry as another standout entry in Eastwood’s illustrious filmography.

5. Gran Torino (2008)

IMDB rating: 8.1/10
Rotten Tomatoes rating: 81%

Storyline:
Gran Torino charts the story of Walt Kowalski (Eastwood), a grumpy, prejudiced Korean War veteran. A series of events leads him to reassess his biases and form an unlikely friendship with a young Asian boy who tried to steal his prized possession – a 1972 Gran Torino.

Why it’s a major performance:
Eastwood’s portrayal of Walt Kowalski marked a new chapter in his career. His character is cantankerous, outwardly racist, and haunted by his past, yet there is a raw humanity beneath his hard exterior. As Walt, Eastwood delivers a masterclass in acting, brimming with empathy and subtle hints of regret and redemption.

Moreover, in Gran Torino, Eastwood tackles the theme of racial intolerance, something new in his oeuvre, handling it with deftness through the complex character of Walt. The film further highlights Eastwood’s ability to keep evolving as a performer, adding more facets to his illustrious acting career, which had already spanned over half a century.

6. A Fistful of Dollars (1964)

IMDB rating: 8.0/10
Rotten Tomatoes rating: 98%

Storyline:
In A Fistful of Dollars, Eastwood stars as the Man with No Name, a wandering gunslinger who arrives in a Mexican town torn apart by rival gangs. He cleverly plays both sides off against each other, leading to a bloody climax in this classic Spaghetti Western.

Why it’s a major performance:
Initial part of the Dollars trilogy, A Fistful of Dollars marked Eastwood’s first significant break into cinema. His portrayal of the Man with No Name, with his trademark squint and minimal dialogue, became a defining role not just for Eastwood, but also for the Western genre itself.

Furthermore, Eastwood’s cool, detached demeanor, and the brutal violence of his character brought a darker tone to the Western genre and marked a departure from the clean-cut cowboys of earlier films. His performance was a game-changer, forever altering the way audiences viewed Westerns and the heroes they portrayed.

7. High Plains Drifter (1973)

IMDB rating: 7.5/10
Rotten Tomatoes rating: 96%

Storyline:
High Plains Drifter, directed and starred by Clint Eastwood, tells the story of a mysterious stranger riding into a desert town and being hired to protect the townsfolk from three outlaws. But as the stranger takes control of the town and the truth about his arrival unravels, the townspeople’s fear increases.

Why it’s a major performance:
In High Plains Drifter, Eastwood offers one of his most ghostly and enigmatic performances. His portrayal of the gunslinger, filled with cryptic lines and ambiguous motivations, gives the film an otherworldly quality. Eastwood’s character is a reflection of the darker, more complicated heroes he had become famous for.

Additionally, beyond his acting performance, the film also stands as a significant achievement in Eastwood’s directing career. Its bleak presentation and harsh critique of community complicity showcased Eastwood’s willingness to challenge and subvert traditional Western genre conventions, a testament to his caliber as an actor and director.

8. Pale Rider (1985)

IMDB rating: 7.3/10
Rotten Tomatoes rating: 92%

Storyline:
In Pale Rider, Eastwood plays a mysterious Preacher who comes to a gold mining community’s aid when they are terrorized by a greedy mining corporation. This character’s arrival and his fight against the oppressors parallel the biblical Four Horsemen’s tale, with Eastwood’s character being a clear embodiment of the “Pale Rider.”

Why it’s a major performance:
Eastwood’s performance as the enigmatic Preacher showcases his ability to play characters shrouded in mystery and moral ambiguity. His stoic, nearly silent portrayal is compelling and infuses the film with a profound gravitas, making it a memorable entry in his Western filmography.

Moreover, the Preacher character furthered Eastwood’s reputation for playing the unsung hero, independent and resistant to corrupt authority. His role in Pale Rider further cements his association with Western genre and his ability to revive and redefine it for contemporary audiences.

9. The Bridges of Madison County (1995)

IMDB rating: 7.6/10
Rotten Tomatoes rating: 90%

Storyline:
In this romantic drama, Clint Eastwood plays Robert Kincaid, a photojournalist who embarks on an all-too-brief, passionate affair with Francesca (Meryl Streep), an Italian war bride living in Madison County. Their four-day romance forms the emotional crux of the film, which explores themes of love, sacrifice, and longing.

Why it’s a major performance:
In The Bridges of Madison County, Eastwood demonstrates his adeptness at playing a character driven by emotions rather than by uncompromising masculinity. His compelling and tender portrayal of Robert Kincaid offers a contrast to the hard-edged characters of his past, showcasing his versatility as an actor.

Moreover, Eastwood’s nuanced performance, coupled with Streep’s, brings a remarkable authenticity to the film’s central romance, making it one of the most significant romantic dramas of the 90s. Despite the departure from his usual roles, his depiction of Kincaid only extended and enriched his highly celebrated screen persona.

10. The Outlaw Josey Wales (1976)

IMDB rating: 7.9/10
Rotten Tomatoes rating: 90%

Storyline:
The Outlaw Josey Wales is a Western film directed by and starring Clint Eastwood. Eastwood plays the titular character, a Missouri farmer whose family is murdered by Union militants during the Civil War. On a quest for vengeance, he becomes a wanted man and a folk hero.

Why it’s a major performance:
Eastwood’s performance as the vengeful Josey Wales adds another iconic Western character to his filmography. His depiction of Josey undergoes a remarkable arc, from a peaceful farmer to a hardened outlaw, providing him with a character that is fleshed out and deeply human.

Moreover, The Outlaw Josey Wales is considered one of Eastwood’s finest Westerns, and his performance as the hardened yet virtuous Josey demonstrates his mastery of the Western hero archetype. His depiction of the avenger pushed to his limit has made the character of Josey Wales an enduring figure in cinema and cemented Eastwood’s place in Hollywood’s pantheon of greats.