The career of Clint Eastwood includes some of the most iconic movies ever, and whether as an actor or director, he has some films that we can’t live without. From coming to define the essence of the lone outlaw in Western cinema to delivering thought-provoking dramas on real-life events, Eastwood has remained at the forefront of pop culture since the 1960s.

The best Eastwood movies stand as timeless classics that have endured throughout the years, as his charismatic demeanor and no-nonsense atтιтude turned him into a true icon. While it’s tough to condense Eastwood’s career down to just a few great releases, these films represent his outstanding legacy and are true must-watch releases.

The Good, The Bad And The Ugly (1966)

While every entry in Sergio Leone’s Dollars Trilogy was fantastic, it was Clint Eastwood’s final outing as The Man with No Name that solidified his status as a Western movie icon. With a cool demeanor, witty one-liners, and iconic aesthetic, few Wild West outlaws have achieved the pop culture relevance of Eastwood in The Good, the Bad and the Ugly.

The combination of Ennio Morricone’s classic score mixed with the iconic three-way standoff in the finale made The Good, the Bad and the Ugly one of the most acclaimed Westerns there has ever been. Although this is a genre Eastwood would return to time and again, it’s difficult to match the impact of this early film.

Dirty Harry (1971)

Clint Eastwood carved out a new kind of action with Inspector Harry Callahan in Dirty Harry. As a classic action movie that helped spawn a whole new genre focused on complicated cops playing by their own rules, Eastwood tapped into a gritty maturity as he played a cop tracking down a serial killer heavily inspired by the real-life Zodiac Killer.

With quotable lines like “Do I feel lucky?’ Well, do ya, punk?,” Dirty Harry led to an entire franchise as Eastwood played the character across five feature films. As a tense and tough action hero, it was Eastwood’s performance that elevated what could have been a standard cop story into something truly iconic.

Thunderbolt And Lightfoot (1974)

While comedy isn’t usually Clint Eastwood’s biggest strength, his greatest comedic role came in Michael Cimino’s directorial debut, Thunderbolt and Lightfoot. Starring opposite Jeff Bridges, this outrageous crime comedy told the story of a disguised preacher who was unintentionally rescued from an ᴀssᴀssination by a car thief.

Eastwood and Bridges made for a compelling duo in a funny comedy filled with robberies, shootouts, and chase sequences. While Eastwood gave a great performance as Thunderbolt, it was Bridges who ended up gaining an Academy Award nomination for his role as Lightfoot.

The Outlaw Josey Wales (1976)

Clint Eastwood’s best Western of the 1970s came with The Outlaw Josey Wales, a fantastic revisionist story directed by the man himself. As an intensely violent revenge tale set during the American Civil War, Eastwood captured the brutality of a man with nothing left to lose as he seeks out the pro-Union militants who killed his wife and son.

The Outlaw Josey Wales allowed Eastwood to go darker than he’d ever gone before and was a powerful exploration of the deepest depths of grief. As a poignant and thought-provoking exploration of America’s violent history, this film not only showcased Eastwood’s talents as an actor but also proved him to be one of the major filmmakers of the 20th century.

Unforgiven (1992)

With an acclaimed career in Westerns behind him, it was only appropriate that Clint Eastwood deliver his definitive statement on this genre as an older man in Unforgiven. As a Best Picture-winning triumph, Eastwood starred as Will Munny, an aging outlaw taking on one last job that forces him to confront the violent past he tried to leave behind.

As a poignant meditation on morality, justice, and the human cost of violence, Unforgiven reflected the brutality of the myth of the American West, and Eastwood excelled as both actor and director. With outstanding supporting performances by Morgan Freeman and Gene Hackman, Unforgiven stands out as one of the best Westerns ever made.

Mystic River (2003)

As an unseen presence, Clint Eastwood’s behind-the-camera work on Mystic River allowed his talents as a director to truly shine through. This intense neo-noir thriller explores how a tragic murder can dredge up the past as three childhood friends are reunited through the investigation into the death of one of their daughters.

With Sean Penn giving an impressive Oscar-winning performance, Mystic River told the story of three Boston boys who were forever harmed after one of them was captured by a child molester. As a film unafraid to explore incredibly dark places, Mystic River followed the classic template of a procedural story, imbuing it with themes of grief, family, trauma, and violence.

Million Dollar Baby (2004)

Clint Eastwood achieved his second Academy Award for Best Director for Million Dollar Baby, an extraordinary sports story where he played the cantankerous, aged boxing coach Frankie Dunn. With Hilary Swank as the underdog boxer Maggie Fitzgerald, audiences would be forgiven for thinking that Million Dollar Baby was going to play out like a kind of female Rocky.

However, the results were much different, as Million Dollar Baby took a sharp narrative turn after Maggie was injured in the ring, broke her neck, and became a ventilator-dependent quadriplegic. From here, Million Dollar Baby transformed into a powerful exploration of life-altering illness and a deeply thoughtful meditation on dignity, mortality, and the moral dilemmas.

Gran Torino (2008)

Clint Eastwood addressed prejudice, racism, and redemption in his powerful drama Gran Torino. With Eastwood as director and star, this story of a recently widowed Korean War veteran alienated from his family became something much deeper when his teenage Hmong neighbor tried to steal his prized 1972 Gran Torino vehicle.

While these circumstances act as the perfect setup to amplify Walt Kowalski’s entrenched racism, Gran Torino instead uses their conflict to spark a dialogue of empathy and mutual respect. Eastwood tapped into his cinematic persona to play gruff, no-nonsense tough guys and subverted the audience’s expectations by having him ultimately discover the possibility of change.

Richard Jewell (2019)

Whether it’s in great movies like Letters from Iwo Jima or Sully, Clint Eastwood has consistently proved his talent for depicting real-life events on screen. An example of this was one hugely underrated Eastwood-directed movie, Richard Jewell, which told the story of the Centennial Olympic Park bombing and its impact on the man who found the bomb.

With an outstanding lead performance from Paul Walter Hauser, Richard Jewell showcased the media frenzy that occurred when this security guard was accused of having placed the device there himself. As a critique of how quick society is to judge without proof and the pitfalls of sensationalism journalism, Richard Jewell was a late-career triumph from Eastwood.

Juror #2 (2024)

It’s a testament to the unmatched work ethic of Clint Eastwood, who’s still regularly releasing new films well into his 90s. Juror #2 is the latest film from Eastwood and stands as a worthy continuation of his legacy as he continues to unpack his core theme of justice in a tense character study about a man in a deep ethical quandary.

Juror #2 starred Nicholas Hoult as a man called up for jury duty who slowly starts to realize he may have been the one responsible for the crime another man is on trial for. As a personal conflict that explores social prejudices and the pitfalls of civic duty, Juror #2 highlights that Clint Eastwood hasn’t lost any of his spark.