Clint Eastwoodis an American icon. Any dispute of that was shot down in the street decades ago, likely by a stoic, silent gunslinger and/or cop that doesn’t play by the rules. From his early days as Rowdy Yates on thegolden era Western seriesRawhideto his supposedswan song legal thrillerJuror #2, Eastwood has carved his career into the granite of Hollywood history. Whether fully retired or not, there’snever a bad time to take a retrospective look at the actor/director/musician’s storied career.
Eastwood’s career, like any actor or filmmaker who has been steadily working for over half a century, has had its ups and downs. The peaks are so great for him that they only serve to make the valleys seem even lower by comparison. Within those valleys, however,there exist a great many wonderful films as well. Good, bad or ugly, these are the ten most essential films of Clint Eastwood’s career.
10’Every Which Way But Loose' (1978)
Directed by James Fargo
Eastwood may be best known for his work in more serious-minded Westerns or crime films that have mined his gritty stare and gravelly vocals for all their worth, butthe actor has, on occasion, shown his more humorous side. Films likethe surpisingly funnyHeartbreak RidgeorGran Torinoused Eastwood’s gravitas as a foil for humor, but could hardly be considered comedies, and whileKelly’s HeroesorSpace Cowboysmay have their devoted fans, there’sno greater Eastwood comedy than the one that teamed him up with a beer swilling orangutan.
Every Which Way But Loosewas seen as a poor career choice for Eastwood at the time, coming off his success as a grizzled action hero, but it also turned out to beone of his biggest hits and even got a sequel. Eastwood plays an independent trucker who moonlights as a bare-knuckle brawler, who also happens to have a pet primate named Clyde. It’s a premise that could only have come out of the 70s and sits comfortably alongside otheropen road comedies likeSmokey and the Bandit. It’s easily Clint’s most lighthearted effort, and is a good place to start for any casual viewer or fans who are only acquainted with his more violent work.
Every Which Way But Loose
9’The Beguiled' (1971)
Directed by Don Siegel
If Clint Eastwood palling around with an orangutan is a culture shock for some viewers, thenThe Beguiledmay require resuscitation. This melodramatic Civil War-set thriller seesEastwood as an injured solider taken in for care at a woman’s seminary school. There’s nary a gunfight in sight or a standoff to be had, just Eastwood, a houseful of women, and a whole lot of messed-up sexual dynamics.
It’s a film that is problematic to say the least, with Eastwood and long-time collaboratorDon Siegelperhaps a little out of their depth when trying to tackle themes of feminine rage or sexual repression. TheSofia Coppoladirectedremake is an improvement, but there is still a lot to admire in the southern gothic original, particularlyEastwood’s somber, subdued performance that is a far cry fromhis other machismo-infused rolesfrom the same period. It’s a beguiling perfomance thats indicative of the range he has as an actor.
The Beguiled
8’Play Misty for Me' (1971)
Directed by Clint Eastwood
Eastwood is just as well known today as a director as he is a movie star. The actor’s desire for more creative control after working under other film and television directors for almost two decades saw him step behind the camera for hisdirectorial debutPlay Misty For Me, a Hitchcockian film that was a precursor toerotic thrillers likeFatal Attraction.
Eastwood stars as a radio DJ who becomes the object of desire foran obsessed fan, played by the late, great Jessica Walters. Much likeFatal Attractionand myriad other crazed women thrillers, the movie doesn’t always look great when viewed under a modern lens but the two leads are terrific, andEastwood proves his directorial chops by competently staging several sequences of suspense. It was the modest beginning to a directorial career that would shape Hollywood for decades to come.
Play Misty for Me
7’Mystic River' (2003)
While Eastwood has headlined or co-starred in the majority of his directorial efforts, there have beena number of notable exceptions where his talents have remained entirely off-screen, particularly in the last couple of decades of his career.Bird, a heartbreaking biopic of Charlie Parker, was an underrated effort that delved deep into Eastwood’s love of jazz music, and he would remain behind the camera for other major films likeAmerican SniperandSully, but the most powerful of all wasMystic River.
Based on the novel of the same name byDennis Lehane, theBoston-set crime drama was a return to form, after a series of uneven films through the 90s and into the 00s. The mystery-thriller follows three childhood friends,whose lives were forever altered after one of them was abducted as a child, brought back together by tragedy. The central performances are all superb, and bothSean PennandTim Robbinswere rewarded with Academy Awards for their work, but Eastwood’s direction is just as noteworthy. It marked theelder filmmaker’s entry into a new matured phase of his career that has carried through to the present.
Mystic River
6’The Outlaw Josey Wales' (1976)
TheWestern genre’s impact is singular in Eastwood’s career, and there are many milestones to choose from.High PlainsDrifterwas his first Western as a director, and his most experimental in the genre, whilePale Rideris an underrated later entry that is very much a companion piece to it. More prominent, though, was the controversial, but highly successful,anti-war WesternThe Outlaw Josey Wales.
Based on a novel by a white supremacist, the film is a revisionist Western revenge story focusing on Eastwood as the titular character, a former soldier of the Confederacy whowages a guerrilla war against the Union soldiers responsible for the death of his family. The controversy of the source material’s author, and clear pro-Confederacy views, notwithstanding,Eastwood crafted an iconic and influential film that became a major touchstone for many filmmakers after. It also had major consequences in the world of film, as Eastwood notoriously fired original directorPhilip Kaufmanand took over himself, leading to a new rule within the Director’s Guild of America that would prevent future stars from doing the same.
The Outlaw Josey Wales
5’A Fistful of Dollars' (1964)
Directed by Sergio Leone
Eastwood as a star is synonymous withthe Spaghetti Western subgenre. Without Eastwood, one of the biggest landmark films,A Fistful of Dollarsmay not have succeeded, and the actor’s career may have faded into obscurity.Sergio Leone’sfilm,a blatant rip-off ofAkira Kurosawa’sYojimbo, only ended up with Eastwood as the lead after a number of higher profile stars, includingCharles Bronson, turned down the role and Eastwood was recommended by another actor.
His performance as “The Man with No Name” (a moniker invented by the American distributor) was far removed from the more altruistic Rowdy Yates, who Eastwood had played for years onRawhide. The iconic antihero is one of Eastwood’s signature roles, andhis work in this film and two more with Leone would catapult him to stardom. Beyond the effects on the actor’s career,A Fistful of Dollarswas the splash that erupted into a tidal wave of Spaghetti Westerns that would emerge from Europe over the next decade plus, andhave influenced entire directorial careers since.
A Fistful of Dollars
4’Million Dollar Baby' (2004)
IfMystic Riverreestablished Eastwood as a top tier director, then boxing dramaMillion Dollar Babycemented that status. The critical and commercial acclaim showed thatEastwood had gallons of gas left in the creative tank, and he was just getting started. It also holds the distinction of being the final film for which Eastwood would win an Academy Award, for directing, and the final time he would be nominated as an actor.
Hilary Swankdelivers a knock-out performance as a lower class waitress, with dreams of becoming a boxer, who comes under the tutelage of Eastwood’s cantankerous trainer. Far from a feel-good sports movie,what begins as another underdog success story turns into a tragedyas Swank’s character suffers an irreversible injury. It’sone of the darkest sports moviesever made, and Eastwood is well suited to capturing the grit and determination of the lead character, right down to the bitter end. Eastwood has often been considered an actor’s director, able to guidegreat performances in many of his films, and there is no better example of that thanMillion Dollar Baby.
Million Dollar Baby
3’Dirty Harry' (1971)
Eastwood may have reprised several roles throughout his career, butnone more than Detective Harry Callahan, the ruthless, determined and politically incorrect officer of the San Francisco police department who uses unorthodox methods to capture and kill bad guys when red tape gets in the way.AlongsideShaftandThe French Connection, released the same year,Dirty Harryset the template for loose cannon cops that would dominate action films through the 70s and 80s.
While the real world implications of cops who ignore things like due process are a nightmare for many underrepresented minority groups,the fictional exploits of Eastwood’s uncompromising cop provide a hell of a lot of entertainment value. Inspired by the real-life killings of the Zodiac,Eastwood’s first outing as the character sees him tracking down a notorious serial killer known as Scorpio. Don Siegel handles the action like a modern day Western, and provides an interesting snapshot of San Francisco at a very tumultuous time in its history.
Dirty Harry
A Fistful of Dollarsmay have been his entry into the genre, andDirty Harrymay be his best known character, but damn ifThe Good, the Bad, and the Uglyisn’t justthe most deliriously entertaining filmof Eastwood’s entire career. Bringing back his laconic outlaw character, here referred to as Blondie, director Sergio Leone makes him part of an iconic Western triptych, facing off againstLee Van Cleef, the Bad, andEli Wallach, the Ugly,foran epic Westernthat is a complete and total masterpiece.
With the Civil War raging in the background, the three leads all vie for a hidden stash of Confederate gold, leading toa series of expertly staged stand-offs and explosive conflicts. Leone is at the height of his directorial powers, alternating between his unparalleled use of long shots and extreme close-ups that were a cinematic language all his own. That direction is complemented byEnnio Morricone’sbeautiful score, and Eastwood’s effortlessly cool performance that anchors the entire film. Endlessly imitated, copied, and riffed on,this Spaghetti Western has never been bettered.
The Good, the Bad and the Ugly
1’Unforgiven' (1992)
In an acting career with asmany distinct eras as Eastwood’shas, anda directorial career that’s just as varied, it can be hard, if not downright foolhardy, to find a singular film that could be considered the pinnacle. But ifUnforgivenisn’t that film, what the hell else could be?Eastwood delivered one of the greatest Westerns ever made, and left a final mark on the genre that made him a star.
As William Munny, a killer outlaw well past his prime, Eastwood brought the entire weight of his career to portray thedeep-felt sadness and loss inherent to a character with such violence in his past. It’s only more violence that brings him out of retirement, as he is hired to avenge the women of a brothel, which brings him into conflict withGene Hackman’svicious Little Bill. It all culminates in a final shootout that is far from triumphant, a fitting end to a dark revisionist Western that ruminates on death. It’sa film that could have only come from a star and director like Eastwood, that is everything up to and including essential.
