The 10 best movies directed by Clint Eastwood

Spencer Stone in a scene from The 15:17 to Paris. (Photo: Warner Bros. Pictures via AP)

At the age of 87, Clint Eastwood shows no signs of slowing down, as evidenced by the fact that the acclaimed filmmaker has yet another new movie in theaters this week. Something of a companion piece to 2016’s Sully, The 15:17 to Paris takes as its subject a real-life tale of heroism: the 2015 Thalys terrorist train attack that was thwarted by three American passengers. Starring the very men whose deeds it recounts, Eastwood’s 36th (!) behind-the-camera feature (many of which he’s also headlined) continues the actor-director’s decades-long investigation into issues of violence and valor. In honor of his latest, we present a rundown of the 10 best films helmed by the enduring, incomparable American icon.

10. Letters From Iwo Jima

The superior half of Eastwood’s 2006 WWII two-hander (the other being the U.S.-focused Flags of Our Fathers), this black-and-white, Japanese-language war epic follows two men — Ken Watanabe’s general and Kazunari Ninomiya’s soldier — during the Battle of Iwo Jima, eventually won by the Americans. Directed with somber grace and sentimentality, the director delivers a complicated and compassionate treatise on bravery and sacrifice.

9. Bird

For his 1988 biopic of legendary jazz saxophonist Charlie “Bird” Parker (played by a commanding Forest Whitaker), Eastwood took an unconventional approach, crafting a free-flowing film constructed from key moments in the man’s tumultuous career and drug addiction-plagued personal life. The result is a haunting, darkness-enshrouded requiem for a great artist, and the many burdens he shouldered.

8. White Hunter, Black Heart

Playing a John Huston-inspired filmmaker who ventures to Africa to make his latest movie, Eastwood is a marvel in this underheralded 1990 drama — and his direction has rarely been as confident. Blending reality and fiction in ways both overt and subtle, the filmmaker maintains rigorous control over his complex investigation of violence, artistic hubris, and man’s relationship to nature, all of which climaxes in unforgettable fashion.

7. The Bridges of Madison County

Eastwood hardly seemed like the logical choice to tackle (and star in) an adaptation of Robert James Waller’s romantic bestseller. And yet working with/opposite Meryl Streep, he brings an elegant, unfussy lyricism and mature mournfulness to this story of an Italian war bride (Streep) who, in 1965 Iowa, has a revelatory affair with a professional photographer (Eastwood).

6. Bronco Billy

Perhaps the most underappreciated entry in the Eastwood canon is this 1980 drama about a New Jersey shoe salesman turned carnival sharpshooter who serves as the father figure to a clan of performer outcasts (including Scatman Crothers and Sam Bottoms). Helmed with a deft hand, this ode to the American dream and the fading myth of the West — also featuring Sondra Locke as an arrogant heiress who joins the traveling show — is as touching as it is amusing.

5. Million Dollar Baby

Eastwood’s second major Oscar-feted triumph (it won Best Picture, Director, Actress for Hillary Swank, and Supporting Actor for Morgan Freeman), this 2004 drama is a heartbreaking story of an aging trainer (Eastwood) who agrees to help an up-and-coming boxer (Swank) become a pro. Tales of regret, atonement, and the sometimes-terrible price of love don’t come more tear-inducingly moving than this.

4. High Plains Drifter

After establishing himself as a new breed of antihero in Sergio Leone’s Man With No Name spaghetti western trilogy, Eastwood tried directing himself as an outlaw with this nightmarish 1973 gem about a mysterious stranger who shows up in a mining town and begins punishing those he deems wicked. Culminating in fire and brimstone, it transforms Eastwood’s familiar desperado into a figure of righteous fury.

3. A Perfect World

Eastwood’s 1993 follow-up to Unforgiven features arguably the finest performance in the career of Kevin Costner, here playing a bandit who takes a young boy hostage while fleeing a Texas ranger (Eastwood) and his partners (Laura Dern and Bradley Whitford). A poignant, psychologically rich portrait of fathers and sons, as well as the false promises afforded by the gun-toting life, it’s about as good as anything Eastwood’s ever done.

2. Unforgiven

Eastwood won his first Best Director Oscar for this modern classic (the film took home four statuettes in total, including Best Picture) about an aging gunslinger reluctantly forced back into the killing business. Elegiac and self-critical, it masterfully straddles a line between providing the guns-a-blazing goods and exposing the awful emptiness of such murderous action — all while boasting standout performances from Best Supporting Actor-winning Gene Hackman, Morgan Freeman, Richard Harris, and the filmmaker himself.

1. The Outlaw Josey Wales

Eastwood’s second directorial stab at a Western remains, 42 years after its 1976 release, his greatest achievement. A gorgeous, thrilling frontier saga, it allows him to imbue his Man With No Name persona with new depths, as well as question — via his character’s relationship with a surrogate family, this after his own clan was killed by pro-Union baddies — the shoot-first worldview that had defined so many of his prior beloved characters. It’s a revisionist genre film with few equals.

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