Clint Eastwood has been a towering figure in cinema since the 1960s, making the challenge clear for anyone new to his films: where to start? For anyone seeking the best Clint Eastwood movies, the journey begins with classics like Sergio Leone’s Dollars trilogy, which unexpectedly transformed the Western genre and launched Eastwood’s status as an enduring screen legend.
Eastwood’s distinctive squint and succinct dialogue style quickly captured the attention of audiences, distinguishing him from other stars of his time. His notable contributions include the Dirty Harry series, Unforgiven, and Million Dollar Baby. Beyond acting, Eastwood has established himself as a prominent director, taking a leading role behind the camera since the early 2000s.
Now in his 90s, Eastwood’s 2024 thriller Juror #2 is expected to be his final film, although his extensive body of work ensures his legacy endures. For those unfamiliar with his career, several key movies offer an accessible path into his filmography.
An Underrated Gem: For a Few Dollars More (1965)
The second installment in the Dollars trilogy, For a Few Dollars More often goes overlooked but represents a critical step in both Eastwood’s and Leone’s artistic development. With a larger budget than its predecessor, the film boasts enhanced production values and a more expansive vision.
Eastwood reprises his iconic role as the terse Man with No Name, whose partnership with Lee Van Cleef’s Mortimer introduces a unique dynamic. Mortimer’s personal quest for revenge adds emotional depth, making their alliance more than a simple bounty hunter team-up, but an unconventional buddy story against a ruthless outlaw.
Despite its length exceeding two hours, the film maintains a brisk pace through engaging characters and memorable sequences. This movie showcases Eastwood’s emergence as a star capable of carrying big productions and serves as an excellent introduction to his Western work.
The Complex Journey of The Outlaw Josey Wales (1976)
While film enthusiasts often highlight Unforgiven and The Good, the Bad and the Ugly as Eastwood’s pinnacle Westerns, The Outlaw Josey Wales stands out as one of his most genuine and entertaining contributions to the genre.
The narrative begins as a straightforward revenge story, with Eastwood’s Josey Wales dispatching enemies with oversized revolvers and sharp remarks. Yet the film evolves, depicting the tough loner forming a makeshift family and rediscovering his own humanity throughout the journey.
Filled with intense action scenes and classic Western motifs, the movie also weaves in anti-war themes subtly. Eastwood’s dual role as lead actor and director brings a compelling emotional arc to the screen, largely conveyed through his restrained dialogue and commanding presence.
Sudden Impact (1983): The Dark Side of Dirty Harry
The Dirty Harry franchise’s original installment is often more nuanced than critics acknowledge, but its sequel Sudden Impact is the raw, violent manifestation many associate with the series. This film, uniquely directed by Eastwood himself, is a striking example of his action hero persona distilled to its essence.
Sudden Impact delivers Harry’s highest body count, arguably the sharpest one-liners—most famously, “Go ahead, make my day”—and highlights Eastwood’s skepticism towards authority. The action sequences are amplified, featuring an upgraded magnum for Harry.
Beyond its surface, the narrative delves into themes of justice and revenge through the story of an assault victim who hunts down her attackers. Her evolving relationship with Harry adds complexity, culminating in a gripping moral dilemma that tests the detective’s principles.
Though its episodic structure and blunt subtext can feel heavy-handed, the film’s intense tone and unflinching outlook give it a powerful impact that remains engaging. The darker content may not be suitable for all viewers but is integral to its lasting impression.
In the Line of Fire (1993): A Veteran’s Final Mission
Clint Eastwood’s characters began to reflect his own aging from Unforgiven onward. Before that, earlier action films like The Dead Pool tried to ignore his aging. This shift of embracing age added depth to his roles, which is particularly evident in In the Line of Fire, a 1993 thriller directed by Wolfgang Petersen.
Eastwood plays Frank, a seasoned Secret Service agent determined to stop an assassin targeting the President. The film immediately signals its difference, with an early scene showing Frank struggling to keep up with the motorcade, highlighting vulnerability.
Supported by a strong cast including Rene Russo, John Mahoney, and John Malkovich, the latter’s portrayal of the would-be assassin steals the spotlight. His antagonist forms a twisted connection with Frank, blending taunts with a troubling psychological bond.
The film embodies the mature, sophisticated thrillers of the 1990s, such as The Fugitive, which are rarely produced today. It reveals a more human side of Eastwood’s screen persona, offering one of his most relatable and multi-dimensional roles.
Gran Torino (2008): Redemption in Later Years
After the disappointing box office performance of Blood Work in 2002, Eastwood stepped away from acting to focus on directing. His selective return came with Gran Torino, a film that, like Unforgiven, grapples with his established on-screen identity.
The narrative centers on Walt, a Korean War veteran living in a Detroit neighborhood who initially harbors strong prejudices against nearly everyone around him, including his Hmong neighbors, portrayed by Bee Vang and others. Walt’s gruff exterior and sharp wit mask a man isolated by his own biases and past.
In one of Eastwood’s finest late-career performances, the character gradually forms an unexpected friendship that reshapes his outlook on life. The film’s conclusion, where Walt chooses to resolve a deadly conflict without violence, signals a clear departure from the star’s earlier, more hard-edged roles.
“Go ahead, make my day” – Clint Eastwood, actor/director
“This sequel is violent, scuzzy and delights in asking uncomfortable questions about the nature of justice and revenge.”
– unnamed critic
“It’s all the more impressive for conveying the lead’s emotional arc with barely any dialogue.”
– unnamed critic
“In the Line of Fire is the type of adult, 1990s thriller like The Fugitive that just doesn’t get made anymore.”
– unnamed critic
“Gran Torino has one of Clint Eastwood’s best latter-day performances, which is special praise since Walt kind of sucks.”
– unnamed critic
Clint Eastwood’s filmography offers several strong starting points for newcomers, reflecting different facets of his evolving persona. From the rugged Spaghetti Westerns with Sergio Leone, through morally complex thrillers and late-career reflections on identity and aging, these five films provide a comprehensive introduction to his enduring impact.
As Eastwood’s career approaches its twilight with Juror #2, the significance of his best Clint Eastwood movies remains clear: they not only entertain but also chronicle the shifting nature of heroism, justice, and humanity across decades. For anyone newly exploring his work, these titles showcase why Eastwood continues to command respect and fascination in the cinematic world.
