15 Essential Clint Eastwood Films You Need To Watch

8. The Outlaw Josey Wales (1976)

The Outlaw Josey Wales

Three years after directing and starring in the malicious High Plane Drifters, in his fifth directional effort, he starred and directed another great western, The Outlaw Josey Wales, which is a bold temperamental dark revisionist western about a Missouri farmer who joins a confederate guerilla unit and ends up on the run from the Union soldiers who murdered his family.

Like his iconic character of Man with No Name, Eastwood once again plays the character of a loner. He once again plays a man with very few words, who lets his action speak for him. However, unlike man with no name, Josey Wales has emotions. He is a man of grand compassion and audacity and his revenge is driven more by that fact that he is tired of all the violence he has seen, not because he craves for it.

Eastwood’s portrayal of Josey Wales is dazzling as one would expect and even more so behind the camera. He makes a classic thrilling adventurous western but he is not bound by the rules. He follows some of them, he breaks some of them and boy, does he break them good. How many westerns can you name which bring together such contrasting storylines and blends them with such subtlety. So if you like an old classic western, go for it, but if you don’t, then watch it because it will make you crave for one.


7. The Beguiled (1971)

The Beguiled (1971)

Adapted from the southern gothic novel A Painted Devil by Thomas P. Cullinan, The Beguiled was the third project of Sigel/Eastwood pair after Coogan’s Bluff and Two Mules for Sister Sara. It is also, the only drama venture of the duo as Escape from Alcatraz is more or less a prison movie per say. This scandalous film is about Corporal John McBurney, a wounded Yankee soldier, who is rescued on the verge of death and nursed back to health by girls and women, of an all-girl boarding school, in the last days of American civil war. But things go wrong when he starts to con his way into the hearts of lonely sexually repressed women.

Never in his career Clint Eastwood, the man who has transcended all genres, has played a character quite like this one before or after this film in his long career of 59 years. He stands stripped of all his machismo and masculinity. He is an unabashed perverted man who enjoys being the object of sexual fascination of all the ladies in that southern boarding school. He understands the psyche and the desires of the women around him and leaves no stone unturned to make the best of it. He in fact, sometimes, flirts with more than one woman at a time however ends up as a poor hunter.

Certainly one of the best by Don Siegel, The Beguiled, a multi-layered psychologically fascinating sexploitation horror war romance, is an intriguing character study that delves deep. It is a sexually charged film which is stimulating and even magnetic to some extent in few acts. Unfortunately, it is one the most under seen Eastwood vehicle. The film was a big flop on its release, the only flop out of the three releases Eastwood had in 1971. It didn’t get any cult following either after all these years, like most other films get, which somehow works in its favor because when you watch it, it surprises you beyond comprehension. A must watch.


6. Dirty Harry (1971)

Dirty Harry (1971)

To say the least is the best way to go about Dirty Harry because anything and everything I could possibly say or can think of saying has been said before, several times. The impeccable collaboration between director Dong Siegel and Clint Eastwood produced an all time classic. Famous for its monologue “I know what you are thinking. Did he fire six shots or five? Well, to tell you the truth, in all this excitement, I’ve kinda lost track myself. But this being a .44 magnum, the most powerful handgun in the world and would blow your head clean off. You’ve got to ask yourself one question- Do I feel lucky? Well, do ya punk?” which became a cultural phenomenon, this ultimate cop film is itself a phenomenon in itself. It gave us one of the most iconic characters ever in the form of Harry Callahan. 


5. Letters from Iwo Jima (2006)

Letters from Iwo Jima (2006)

Directed by Eastwood, Letters from Iwo Jima tells the story of the battle of Iwo Jima between United States and Imperial Japan during World War II, as told from the perspective of Japanese soldiers who fought the war. Though it was an American co-production, it was shot almost entirely in Japanese language. It was a companion piece to director Eastwood’s Flag of Our Fathers, his first film about the war of Iwo Jima, The first film was in English and it was told from the perspective of American. Both the films were shot simultaneously and were released in the time span of two months.

This thought provoking story of a ruthless war is powerful and benevolent. Among the horrors of war where you watch people blow themselves by grenades and humans die like flies, Eastwood creates moments when a Japanese soldier, after shooting his Enemy, takes him in his cave and cures him. Outside the cave both sides are going about their business of killing each other, blowing heads, taking the heads of fathers of innocent children, turning innocent women widows, inside the cave the Japanese soldier and the American talk about soldier’s American acquaintance. This scene captures the essence of the film which stays beautiful and humane in spite of all the death, agony, pain and horrors of battle.

There are so many great movies about war but what is unique about Letters from Iwo Jima is that it is more about the people involved in the war then the war itself. It’s more about soldiers as people than as instruments of the country they fight for. It succeeds where so many war movies have failed, to go beneath the uniform and make us see soldiers from both sides as human beings, made of flesh and bone with feelings and emotions, at the same time.


4. Gran Torino (2008)

gran torino

Clint Eastwood directed and starred in yet another sensational film in which he retains his macho image yet successfully manages to find new grounds to break. Gran Torino, small on scale, grand in its idea and big on heart, is about relations, friendship, bonding, revelation, religion, ethnicity and toll of war on a person. It is about an old man. It is about that old man forming a bond with people he thinks he hates. It is about a car. It is about revenge but above all it is about revelation.

Walt Kowalski (Clint Eastwood), a recently widowed Korean War veteran, sits all day on his porch drinking beer and chewing tobacco. He lives alone and he has a Hmong family living next door. He isn’t very fond of the idea. Kowalski bonds with Thao (Bee Vang) and her sister Sue (Ahney Her) as he accepts Thao’s help as an apology, after he tries to steal his Gran Torino and Walt saves him from the gang who conspired the plan. What follows is the process of bonding, brewing troubles and a sensational ending.

Gran Torino starts slow and in the beginning it wanders around known premises, but all of a sudden it becomes much more than you think it could. Like Kowalski, it transgresses the boundaries and ends on such high note, one of the best drama endings ever, that it will leave your heart in your mouth and tears in your eyes. In the long list of movies he directed and starred in, this is the last entry and it is a perfect adieu.


3. Unforgiven (1992)


Now that’s how you make a western! Eastwood directed and starred in Unforgiven (nominated for 13 academy awards) which earned him his first and second academy awards, for best director and best picture (the third western to achieve the feat). The film is about William Munny (Clint Eastwood in his Oscar nominated performance), an old man who is a farmer now, but he has a history. He was a gunslinger and a cold blooded murderer in the past. The ageing outlaw turned farmer halfheartedly takes one last job with his old partner Ned Logan (Morgan Freeman) and a young man the Schofield kid (Jamiz Woolvett).

“The last western” directed by Eastwood is easily one of the best western films ever made and there is a reason for it. Like all old classics it has vengeance and violence but among all the violence and the gangs of old Wild West, there is a deep study of human character, like all great films. It also deals with the uglier aspect of violence and comes with highly persuasive opinion in regard to the violence.

Another unique feature of Eastwood’s amazing western is that it doesn’t really take place in the old wild west. People have changed their way of living and they have reason, stories behind their life, some true and some distorted version of a complicated truth, exposing you to the truth behind the change stripped, bare. It introduces the moral question of life but it never gets preachy. Eastwood dedicates this movie to two deceased director whom he sited as his influences in his filmmaking, Sergio Leone and Don Siegel, and he sure as hell makes them proud.


2. Million Dollar Baby (2004)


It’s about a tough girl with a big heart and an indomitable will, who wants to make her mark in the world of professional boxing. Margaret “Maggie” Fitzgerald (Hilary Swank), a working waitress, to realize her dreams tries to convince Frank Dunn (Eastwood), a brilliant yet not very successful trainer to train her. Eventually she does and from there starts a simple yet incredible journey. The film won four Oscars, two for Eastwood (best picture and best director), one for Morgan (best supporting actor) and one for the knockout punch to Hilary Swank (best actress).

After Unforgiven, Morgan Freeman and Eastwood paired again for a sensation Million Dollar Baby and made history once again. Directed by Eastwood, starring him, vintage actor Freeman and terrific Hillary swank in her career best performance, Million Dollar baby, is a masterpiece. It’s not a rags to riches story. It’s not a sports drama where an underdog crosses all the hurdles to win the world to bring tears in your eyes. This story is certainly going to bring tears in your eyes but in a totally unexpected manner. This is a story which is simple yet thoughtful, powerful and very stirring. It is also very honest in terms of what it says and flawless in terms of how it says that. Eastwood’s masterpiece is a perfectly crafted balanced act which is about love more than anything else.


1. Dollars Trilogy/The Man With No Name Trilogy (1964, 1965, 1966)

the good the bad the ugly

Sergio Leone and Eastwood collaborated in mid 60s and made one of the best trilogies and three of the greatest westerns ever made. The three spaghetti westerns, Mecca of western films, starred Clint Eastwood as the iconic Man with No Name and gave a perfect start to an unbelievable career of the great legend.

First film in the trilogy, A Fistful of Dollars, tells the story of a mysterious young wanderer (Eastwood) after arriving in San Miguel, a small town on the border of Mexico, plays two rival families against each other.

The second outing, For a Few Dollars More, an instant classic of the genre, is about two bounty hunters, the man with no name – Manco (Eastwood) and Col. Douglas Mortimer – the man in black (Lee Van Cleef), who team up to track down an infamous outlaw – El Indio (Gian Maria Volonte).

The third film in the trilogy, The Good, The Bad and The Ugly is about three men trying to beat each other in a race to find the buried fortune.

Crafted in style by the greatest director of spaghetti westerns, Dollars had three main pillars. Grand vision and extremely stylish direction of Sergio Leone complimented wonderfully by Ennio Morricone’s score and Eastwood living a dream on the screen. All three films, monumentally influential, pack a punch. Morricone’s whistles, Eastwood’s Cigar, unsympathetic backdrops, extreme close-ups, sparse dialogue, extended duels, enhanced sound effects, compelling stories and great on screen presence and performances amalgamate and the end product is memorable and ageless. This epic trilogy, which stars Eastwood in his most influential role is also the best of his illustrious career.