Best movies directed by Clint Eastwood

WB

At 91 years old, Clint Eastwood is still directing movies, and his latest film 'Cry Macho' will open on September 17.  Few actors have been as successful as Eastwood when it comes to making the transition from acting to directing. We ranked Eastwood's best movies as a director.

12. 'High Plains Drifter' (1973)

Clint Eastwood in High Plains Drifter movie in 1973

Universal

It's not quite as highly regarded as the most iconic of Eastwood's many Western movies (in part because of the controversial rape scene early on), but "High Plains Drifter" served as an early sign that Eastwood had as much promise behind the camera as in front of it. It's also a Western that pushes the boundaries of the genre. It's as much a ghost story and a revenge thriller as anything else.

High Plains Drifter
High Plains Drifter
"Welcome to Hell"
75
R1 hr 45 minApr 19th, 1973


11. 'Bronco Billy' (1980)

Clint Eastwood in Bronco Billy movie in 1980

WB

While Eastwood once again cast himself as a gruff cowboy in "Bronco Billy," this movie is -- tonally -- a complete departure from his usual fare. It's an unexpectedly charming look at a traveling circus and its main attraction, a trick-shooting cowboy trying to hold it all together. "Bronco Billy" is a nice reminder that Eastwood can be a great comedian when he puts his mind to it.

Bronco Billy
Bronco Billy
"The most outrageous of 'em all."
63
PG1 hr 56 minJun 11th, 1980


10. 'Bridges of Madison County' (1995)

Clint Eastwood in Bridges of Madison County movie in 1995

WB

Even a guy like Eastwood feels the urge to try his hand at a romantic drama now and then. While a bit sappy in the way so many of these films are, "Bridges of Madison County" is a top-notch adaptation of the novel that benefits greatly from the chemistry only Eastwood and Meryl Streep can provide.

The Bridges of Madison County
The Bridges of Madison County
"The path of Francesca Johnson's future seems destined due to an unexpected fork in the road..."
77
PG-132 hr 15 minSep 28th, 1995


9. 'Gran Torino' (2008)

Clint Eastwood in Gran Torino movie in 2008

WB

Eastwood has a well-honed reputation for playing some of the toughest, crabbiest heroes in Hollywood. "Gran Torino" stands out because it turns that reputation on its head. Eastwood plays one of his most memorable characters here, an old rabble-rouser and Korean War veteran drawn into a neighborhood conflict involving Hmong American gang members. It's easy to picture a lot going wrong given the movie's racially charged elements, but instead the result is arguably Eastwood's best film of the 21st Century.

Gran Torino
"Ever come across somebody you shouldn't have f#cked with?"
80
R1 hr 56 minDec 9th, 2008


8. 'Mystic River' (2003)

A scene from Mystic River movie in 2003

WB

"Mystic River" is one of those films we can't help but wonder if Oscar voters went a little overboard in honoring at the time. Still, it's a worthy addition to the Eastwood canon by any measure. The performances are uniformly terrific, and the film offers a sobering look at the lingering impact a terrible crime can have on a group of lifelong friends.

Mystic River
"We bury our sins, we wash them clean."
77
R2 hr 18 minOct 8th, 2003


7. 'Pale Rider' (1985)

Clint Eastwood in Pale Rider movie in 1985

WB

For the most part, audiences were pretty well burnt out on Westerns in the 1980's. But there's always room for another good Western directed by and starring Eastwood. With its religious undertones and its commentary on America's consumer-driven mania of the mid-'80s, this is a Western with a lot of meat on its bones.

Pale Rider
Pale Rider
"...and hell followed with him."
72
R1 hr 55 minJun 28th, 1985


6. 'Bird' (1988)

A scene from Bird movie in 1988

WB

A lot of "Jersey Boys" fans were underwhelmed by Eastwood's take on the popular stage musical. Luckily, he found far more success with this biopic about jazz legend Charlie "Bird" Parker. Sure, it plays a little fast and loose with history, but it's a fascinating (and underrated) glimpse into the life of a true artist, an artist played with gusto by the excellent Forest Whitaker.

Bird
Bird
70
R2 hr 41 minSep 30th, 1988


5. 'Million Dollar Baby' (2004)

Clint Eastwood in Million Dollar Baby movie in 2004

WB

Every year, it gets a little harder for boxing movies to make their mark. It's one genre that has been done to death over the years. Yet that didn't stop Eastwood from crafting what many regarded as the best movie of 2004 with "Million Dollar Baby." The dynamic between Eastwood's gruff trainer and Hilary Swank's ambitious boxer is a highlight, and more than enough to make up for the somewhat unsatisfying ending.

Million Dollar Baby
"Beyond his silence, there is a past. Beyond her dreams, there is a feeling. Beyond hope, there is a memory. Beyond their journey, there is a love."
80
PG-132 hr 12 minDec 5th, 2004


4. 'A Perfect World' (1993)

A scene from A Perfect World movie in 1993

WB

Perhaps Eastwood's most underrated film, "A Perfect World" stars Kevin Costner as an escaped fugitive who befriends a young boy and Eastwood as the Texas Ranger hellbent on bringing them in. Basically, Eastwood's take on "Les Miserables." Costner's terrific performance -- and Eastwood's deft hand behind the camera -- work to deliver a truly compelling drama on par will Mallick's "Badlands."

A Perfect World
A Perfect World
75
PG-132 hr 18 minNov 24th, 1993


3. 'Letters From Iwo Jima' (2006)

A scene from Letters From Iwo Jima movie in 2006

WB

This companion piece to 2006's "Flags of Our Fathers" opted to explore the infamous Battle of Iwo Jima from the Japanese perspective for a change. In the process, it wound up far surpassing its companion. Everything here, from the acting to directing to cinematography, is top-notch Eastwood. This film also proves that Eastwood can succeed just as well even when directing a script that's mostly non-English.

Letters from Iwo Jima
"The battle of Iwo Jima seen through the eyes of the Japanese soldiers."
75
R2 hr 21 minDec 19th, 2006


2. 'The Outlaw Josey Wales' (1976)

Clint Eastwood in The Outlaw Josey Wales movie in 1976

WB

The Western genre was past in prime by the time the '70s rolled around, but Eastwood proved he had plenty more to say by strapping on his boots and six-shooters. "The Outlaw Josey Wales" is a true Western for the Vietnam era, despite being set during the Civil War. It's a staunchly anti-war film that reflects on America's deeply troubled past and the importance of family.

The Outlaw Josey Wales
The Outlaw Josey Wales
"...an army of one."
75
PG2 hr 15 minJun 26th, 1976


1. 'Unforgiven' (1992)

Clint Eastwood in Unforgiven movie in 1992

WB

You'd think after a career that includes timeless classics like "The Man With No Name Trilogy," "The Outlaw Josey Wales" and "Hang 'Em High," Eastwood would have nothing left to contribute to the Western genre. Instead, he saved his best effort for "Unforgiven." This haunting tale of an ex-bandit dragged back into the hard life easily ranks among the best Westerns of all time. It abandons the romance and adventure of classic Westerns for a more frank, even bleak look at life on the frontier. "Unforgiven" truly earned its Best Picture Oscar that year.

Unforgiven
Unforgiven
"Some legends will never be forgotten. Some wrongs can never be forgiven."
79
R2 hr 10 minAug 7th, 1992