Celebrating his 90th birthday earlier this year, Clint Eastwood has enjoyed a career spanning more than six decades. His first big break was portraying the cattle driver Rowdy Yates in the long running western series, Rawhide. This role catapulted Eastwood into an iconic western star with one of the movies below being filmed before his role as Yates concluded. He has more than 70 acting credits to his name and has directed more than 40 films with Oscar nominations and wins among them. His roles have included playing outlaws, cowboys, rogue detectives, American soldiers, and just a little of everything in between.
This legend of cinema has been instrumental both in front of and behind the camera. And while his filmography dates back further than the lives of most people reading this article, we’re going to “go ahead and make your day” by listing the best Eastwood films.
However, “if you’re feeling lucky,” try to guess which ones are tops before scrolling down the list.
11. Bridges of Madison County – 1995
This movie is an anomaly on this list as Eastwood plays a character unlike his previous roles. Based on the 1992 bestselling book, Robert Kincaid (Eastwood) is a National Geographic photographer sent on assignment to rural Iowa to capture the covered bridges in the county. Meryl Streep portrays a married housewife living on a farm who has an affair with the photographer while her husband and her children are out of town. Though the episode is a brief one, Streep’s character recounts the illicit affair in her private journals that her children discover and read after her death.
10. Hang ‘Em High – 1968
Jed Cooper (Eastwood) is captured and accused of cattle rustling and murder before being unsuccessfully lynched by a gang of vigilantes. Saved by a U.S. Marshal, it is later discovered that Cooper was not guilty of the crimes. The judge (Pat Hingle) convinces Cooper to return to his former life as a lawman. This allows him to systematically hunt down the nine men that tried to hang him and left him for dead.
9. Million Dollar Baby – 2004
This fictional boxing flick would earn Eastwood an Oscar nomination for Best Actor in a Leading Role and wins for Best Picture and Best Director (along with another Golden Globe win in this category). Frankie Dunn (Eastwood) is a veteran boxing trainer who reluctantly takes on an ambitious 31-year-old female boxer, Maggie Fitzgerald (Hilary Swank). After Maggie is gravely injured in a match, Dunn must make a decision on whether to carry out her final wishes. The film also stars Morgan Freeman who plays Eddie “Scrap-Iron” Dupris, assistant to Dunn at the boxing gym and also the narrator of the film.
8. Pale Rider – 1985
When a mysterious preacher appears in a small prospecting village (after a young girl prays for a miracle), chaos and death follows. Preacher (Eastwood), rides into town on a pale horse. And of course that’s a reference to the Four Horsemen of the Apocalypse. When a greedy mining tycoon looks to destroy the livelihoods of the prospectors, Preacher works to turn the table and ensure their safety.
7. Dirty Harry – 1971
“You’ve got to ask yourself a question: “Do I feel lucky?” Well, do ya, punk?” This is likely the most iconic line spoken in any Eastwood film. “Dirty” Harry Callahan (Eastwood) is a San Francisco inspector who is quick to use his 44 Magnum and was doing so when he uttered the famous line above in the course of a shootout. The film was highly popular and four sequels followed, all featuring Eastwood as Dirty Harry.
6. Escape From Alcatraz – 1979
From San Francisco cop (Dirty Harry) to Alcatraz inmate, Eastwood portrayed Frank Morris who seeks to escape from one of the most infamous prisons in the world. Based on actual events, Morris and two other inmates are able to slip away from the island in 1962 and disappear without a trace.
5. The Outlaw Josey Wales – 1976
Directed by and starring Eastwood, Josey Wales saw his family murdered by a band of Union soldiers in Missouri during the Civil War. Hell bent on revenge, Wales joins a Confederate band of guerrilla soldiers. Wales’ captain urges the group to surrender to the U.S. Army, Wales refuses to join the bunch and he watches as they are massacred. A bounty is placed on Wales’ head and he is pursued by the same individual that killed his family.
4. High Plains Drifter – 1973
This western was both directed and starred Eastwood as the Stranger who rides into the small isolated mining town of Lago. Upon arriving, the Stranger kills some men and then is asked by the residents to defend the town from three outlaws that are coming back to Lago to settle a score with the town. Little do the residents know, the Stranger is exacting revenge and exposing the corruptness that exists in Lago.
3. Unforgiven – 1992
Released almost two decades after the above movie, this film, like Million Dollar Baby, earned Eastwood another Oscar nomination for Best Actor in a Leading Role and won for Best Director and Best Picture. When a prostitute’s face is slashed by a couple of cowhands, Sheriff “Little Bill” Daggett (Gene Hackman) settles the dispute by making the cowhand’s pay for the assault with ponies (in the future). The prostitutes pool their money and put a $1,000 bounty on the perpetrators. A young gunslinger visits William Munny (Eastwood), an aging outlaw and killer turned farmer, and asks for his help for a split of the bounty. Together, with the added assistance of Ned Logan (Morgan Freeman), they set out for Big Whiskey and are confronted with the authoritative rule of Little Bill.
2. The Good, The Bad, And The Ugly – 1966
This was the final installment in the Dollars Trilogy (aka the Man With No Name Trilogy), a series of three spaghetti western films directed by Sergio Leone. Blondie, played by Eastwood (The Good), is a professional gunslinger who is out to find a stash of stolen gold before The Bad and The Ugly do. Blondie is a loner and is by no means actually “good.” His goal is profit and he must outsmart (and perhaps outgun) his rivals who are after the same prize.
1. A Fistful Of Dollars – 1964
The first in the Dollar Trilogy, also known by its Italian name Per un pugno di dollari, was a spaghetti western staring Eastwood that was filmed in Italy and later brought to the U.S. In it, Eastwood portrays an unnamed stranger who rides into the border town of San Miguel. Once there, he quickly learns of two rival gangs and plays them against one another for his own gain. After being injured, he escapes the town hidden in a casket. He returns with a steel plate hidden beneath his poncho and dares one of the Rojo brothers, Ramón, to shoot him in the heart. The bullets bounce off and in true Eastwood fashion, he kills the bad guys and rides off into the sunset.
Seen all these? Check out our ranking of Quentin Tarantino’s best movies next.
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