Primer is The A.V. Club’s ongoing series of beginners’ guides to pop culture’s most notable subjects: filmmakers, music styles, literary genres, and whatever else interests us—and hopefully you. This week: Clint Eastwood, the 79-year-old actor-turned-director whose yeoman work on both sides of the camera has established him as a critical and audience favorite.
Clint Eastwood 101
If Clint Eastwood never made a movie, he would still be remembered, albeit faintly, as one of the stars of the long-running television Western Rawhide. For eight seasons, he played the character of Rowdy Yates alongside Eric Fleming, who like him, graduated from B-movies to TV stardom. Eastwood had bigger plans, however, when he accepted the lead role in A Fistful Of Dollars, a Western remake of Akira Kurosawa’s Dashiell Hammett-inspired samurai movie Yojimbo, shot in Spain and helmed by the largely untested Italian director Sergio Leone. The gamble paid off. Using European locations to stand in for the Old West, Leone defined (though he didn’t create) the genre later dubbed “spaghetti Westerns.” The film took a cockeyed approach to the myths of the American West, balancing sardonic humor and cranked-up violence with hints of outsized emotion that would grew more pronounced with subsequent films.
The film was an instant success in Europe, in no small part thanks to Eastwood’s tight-lipped, poncho-clad performance as a non-traditional good guy. Though someone calls him “Joe,” he never states his name, and the character became known internationally as The Man With No Name. Reprising the persona, if not the exact character, in two Leone films—For A Few Dollars More (1965) and The Good, The Bad And The Ugly (1966)—Eastwood became the cowboy hero the decade demanded. He played a rebel who scoffed at authority and followed no apparent moral code, though he did tend to end up helping those in need. When the Man With No Name films hit America—rolling out one after another in 1967—Eastwood’s character became as iconic as the cowboy heroes he was meant to displace.
A less-determined actor would have a hard time getting past that kind of remarkable success. Unavoidably, Eastwood’s subsequent Westerns often comment on the indelible character he created for Leone, some brilliantly (like High Plains Drifter) and others less successfully (like the 1985 Shane-meets-Leone effort Pale Rider) but rarely dully. But Eastwood had bigger plans than a lifetime of oaters. Opting out of Leone’s Once Upon A Time In The West—which turned out just fine without him—Eastwood set about trying on different sorts of roles while learning the craft of filmmaking firsthand. To this end, no one was more important to his development than director Don Siegel, with whom Eastwood worked periodically until the end of Siegel’s career.
In 1971, Siegel gave Eastwood his second most famous role, as the title character of Dirty Harry. Though four sequels dulled the original’s impact, Dirty Harry remains today what it was at the time: a powerfully made, ethically slippery examination of the uncomfortable space where the need for law and order meets our treasured civil liberties. Eastwood plays Harry Callahan, an old-school San Francisco cop baffled by his city’s transformation into a paradise for the counterculture. The film puts Eastwood in pursuit of the “Scorpio Killer,” a murderous hippie modeled after San Francisco’s real-life Zodiac Killer. But where Zodiac proved elusive, the film gives Scorpio the taunting face of Andy Robinson, who uses the loopholes of legal protection to turn his life of crime into a taunting, almost flirtatious game, designed to frustrate his most dedicated pursuer. Dirty Harry is a willfully provocative piece of filmmaking that works both as an action film and as a teasing attempt to show the limits of liberal pieties. In some situations, maybe it doesn’t hurt to have a man with a big gun around, keeping the world safe. On the other hand, Harry’s passion for the job—and the ease with which he opts for violence—suggests that those who pursue justice relentlessly often end up looking a lot like the monsters they hunt.
The 1979 prison flick Escape From Alcatraz was Siegel and Eastwood’s final collaboration, and it isn’t as immediately impressive as Dirty Harry. Eastwood plays a career criminal who gets sent to The Rock after multiple escape attempts; there, he meets a colorful cast of fellow inmates (including Fred Ward and Larry Hankin), and a sadistic warden played by Patrick McGoohan. Driven to distraction by the warden’s cruelties and by his own restless intelligence, Eastwood works on finding a way out of America’s best-protected prison. Escape is in many ways a precursor to The Shawshank Redemption, with a lot of the same beats—arrogant authority, old men dying needlessly, surreptitious hole-digging—but without much of the latter’s sentiment. Yet that’s one of the movie’s strengths. Escape From Alcatraz doesn’t have much to say about the mistreatment of prisoners, and none of the characters grow beyond their archetypes, but the film’s straightforward efficiency is surprisingly gripping, especially once Eastwood and pals start putting their plans into motion. As a piece of Eastwood’s cinematic oeuvre, it’s slight; as a rainy-Sunday afternoon distraction, it’s top-notch.
The same could be said of 1993’s In The Line Of Fire, which marks the last time (to date) that Eastwood has starred in a movie directed by someone other than himself. And frankly, Wolfgang Petersen’s thriller—about an aging Secret Service man taunted by would-be assassin John Malkovich—feels more like an Eastwood film than a Petersen film. In spite of Malkovich’s scenery chewing and the producers’ attempt to create a Dirty Harry-esque catch-phrase (“That’s not gonna happen!”), what lingers longest about the movie is Eastwood’s low-key performance. He plays a creaky jazz-lover who relies more on his wits than his physicality, and just by holding still, he forces everyone sharing the frame to slow their pace accordingly. Thus Eastwood assumed control of a summer blockbuster that wasn’t technically his responsibility.
When he transitioned into directing, Eastwood took what he’d learned from Siegel and Leone, combining their techniques with his own unexpectedly offbeat sensibility in a string of popular action movies and Westerns. Eastwood’s first major critical and commercial success as a director came with a Western—and one he wasn’t even supposed to be helming. Philip Kaufman wrote an adaptation of Forrest Carter’s novel The Rebel Outlaw: Josey Wales and signed on to direct, but Eastwood balked at Kaufman’s take on the material, and had him fired mid-production. The final version of The Outlaw Josey Wales feels more like an Eastwood film—mixing frank sex and violence with broad comedy and iconic Americana—than something by the more poetic Kaufman. In telling the story of a Confederate soldier on the run from a vicious Union militia, Eastwood eschews sentimentality by portraying even good men as hard-boiled, and by showing violent action as frequently justifiable. Outlaw is hardly a grim slog. The characters are outsized and the dialogue colorful. Unlike other revisionist Westerns of the ‘70s, The Outlaw Josey Wales wasn’t trying to be challenging or allusive. Eastwood intended only to spin a yarn, and ultimately, the way he spun a blood-spattered, two-fisted tale into a crowd-pleaser proved revolutionary.
For his 1971 directorial debut, Play Misty For Me, Eastwood opted not to get too ambitious… at least on the surface. Taking on a tightly plotted genre movie, Eastwood cast himself as a California jazz DJ who makes the mistake of bedding his biggest fan, a woman who regularly requests the song “Misty.” She’s played by Jessica Walter, whom most modern viewers know best as boozy Lucille Bluth from Arrested Development; here, she gives an alluringly unhinged performance that gets more frightening as the movie goes along. Where most first-time directors make the mistake of going for a big statement right off the bat, Eastwood chooses to serve the story first, and to fill out the details with neat touches, from the shots of his beloved coastal California to a great jazz soundtrack to a New Wave-influenced love scene set to Roberta Flack’s “The First Time Ever I Saw Your Face.” (The latter would look like camp if it weren’t so pretty.) He’s clearly pacing himself, but even from the beginning, it’s clear Eastwood had skills and depths behind the camera that even his best performances in front of it had yet to suggest.
Eastwood also had a broader range of cinematic interests than was immediately apparent from his acting résumé. Though he followed Play Misty For Me with a Western—the wildly unhinged High Plains Drifter—he followed that with a movie so unexpected that it’s frequently ignored when people discuss his directorial career. The 1973 drama Breezy stars Kay Lenz as a carefree hippie who wanders onto the property of uptight establishment type William Holden and strikes up a conversation about values that lasts for days. Breezy’s premise was fairly typical of the time—and even a few years out of date—but Eastwood doesn’t approach Jo Heims’ screenplay as though it were some creaky social statement. He makes Breezy a movie about two people getting to know each other first casually, then intimately.
Eastwood repeated that approach 20 years later when he was tapped to direct Richard LaGravenese’s adaptation of Robert James Waller’s sappy bestseller The Bridges Of Madison County. LaGravenese left Waller’s tearjerker plot intact, with a traveling photographer romancing a lonely Iowa housewife, but Eastwood slowed the tempo down, focusing on the quiet interactions between the housewife (played by Meryl Streep) and the photographer (played by Eastwood himself). Their love affair evolves so naturally that its inevitable end feels all the more painful—like losing a limb.
Why does Eastwood occasionally step outside what seems like his comfort zone? Perhaps it’s that same streak of arrogance that led him to wrest control of Josey Wales from the formidable Philip Kaufman—or to run for mayor of Carmel, California. Eastwood seems to have concrete ideas about How Things Should Be Done, and he isn’t averse to stepping in and giving demonstrations. In some ways, Eastwood’s direction of the slapdash comedy Bronco Billy feels like his subtle reaction to Every Which Way But Loose and Any Which Way You Can, the two wacky-orangutan movies he made around the same time. Bronco Billy is every bit as absurd as those two hits. The movie tracks the incompetent-but-self-satisfied impresario of a modern-day Wild West show as he kidnaps heiresses, stages train robberies, and breaks up bank heists—all to help promote his show. Bronco Billy’s wild plot and controlled tone were an odd mix for 1980, ranging much closer to Preston Sturges and Ernst Lubitsch than to Hal Needham.
As a director, Eastwood tends to thrive or stumble based on the quality of the script he’s working from. In 1985, during a brief revival of interest in Westerns, Eastwood returned to the concept of the avenging drifter in Pale Rider, a routine shoot-’em-up that looked refreshingly old-fashioned at the time, but now comes off as somewhat stale. With 1992’s Unforgiven, on the other hand, he connected with a famously unproduced screenplay that had been kicking around Hollywood for a couple of decades: David Webb Peoples’ The William Munny Killings, a thorny examination of justice and morality. Eastwood stars as a notoriously merciless gunslinger trying to raise his children according to the principles handed down to him by his beloved, late wife. He makes a lousy farmer, though, so to survive, he decides to help collect the $1,000 bounty placed on two cowboys accused of maiming a prostitute. But tough sheriff Gene Hackman is intent on keeping the peace whether or not right prevails against wrong. Can Eastwood channel his old, violent instincts to good ends? Are the compromises of civilization worth the peace and quiet? And why are movie audiences attracted to men with such notoriously vicious dispositions? Filled out by fine performances from Morgan Freeman, Richard Harris, and others, Unforgiven supplies no answers as it lurches toward its moment of reckoning. But answers aren’t really the point. Eastwood’s masterpiece is about a sinner’s struggle to find redemption and meaning in the midst of blood, dust, and silence.
If Bronco Billy was Eastwood’s answer to Every Which Way But Loose, then A Perfect World might’ve been his response to In The Line Of Fire. Again he played a grizzled lawman—this time, a Texas ranger in pursuit of fugitive kidnapper Kevin Costner—and again he paired with a naïve young woman. (For In The Line Of Fire, it was Rene Russo as a novice Secret Service agent; in A Perfect World, it’s Laura Dern as a junior criminologist.) But from the opening shot of a pastoral idyll—an Eastwood trademark—it’s clear that A Perfect World isn’t going to be as sleek and straight as the movie Eastwood starred in six months earlier. As scripted by John Lee Hancock, A Perfect World is an off-kilter contemplation of tradition and honor, and how the stain of violence spreads even among those fighting hard to redeem themselves. A Perfect World was Eastwood’s directorial follow-up to the Oscar-winning Unforgiven, and it was treated at the time as a disappointment, though in retrospect, it’s a very similar story. Toward the end of the movie, Eastwood’s character puts his gun down in front of a pile of candy, and in that one shot, Eastwood recapitulates what Unforgiven was saying about the enduring American infatuation with violence.
The key relationship in A Perfect World is between Costner’s boyish ne’er-do-well crook and the child he abducts, then tries to mentor. In the 1982 drama Honkytonk Man, Eastwood plays a sickly country singer who takes his pre-teen nephew on the road, intending to teach him about life while he approaches an engagement at the Grand Ole Opry. Typical of movies Eastwood directs, Honkytonk Man is rendered in broad strokes and leavened with crude humor. But it’s also lyrical and sweet, and is one of the first Eastwood movies where his love of music (and music-makers) burns steadily throughout.
A lifelong jazz enthusiast, Eastwood paid direct tribute to one of the form’s greatest players with the 1988 Charlie Parker biopic Bird. The movie is, as befits jazz, an odd-angled valentine, portraying Parker as a man whose skills and innovative playing were matched only by his addiction and self-destructive urges. Forest Whitaker’s openhearted lead performance anchors a long film that compensates for its occasional unwieldiness by avoiding biopic clichés. Whitaker’s Parker falls victim to his addiction even while he’s redefining what jazz means. There’s no loss of innocence here, just sickness and wasted potential. In the film’s final scenes, he’s become a man out of time, adrift in a world he helped create.
Eastwood’s no-nonsense approach and command of actors were put to the test by the 2003 Dennis Lehane adaptation Mystic River. At times, Sean Penn, Tim Robbins, and Kevin Bacon all seem like they’re in some kind of Method competition for the audience’s attention. In the end, however, the tragic story and mournful atmosphere win out. It’s an effective, occasionally wrenching movie, but the following year’s Million Dollar Baby served as a reminder that Eastwood had even better films in him. Eastwood’s second Best Picture-winner turns the story of a female boxer (Hilary Swank) and her reluctant trainer (Eastwood) into a devastating examination of the obligations that come with being part of a family, even when that family has no real blood ties.
Immediately following the critical and box-office triumphs of Mystic River and Million Dollar Baby, Eastwood tackled his most ambitious project to date: the paired World War II films Flags Of Our Fathers and Letters From Iwo Jima. The former tells the story of the American soldiers who raised the flag at Iwo Jima, and how their stateside lives were stage-managed by Army PR to the point where their actual wartime experiences became irrelevant. The latter recounts The Battle Of Iwo Jima from the Japanese perspective, as the Japanese argue among themselves over whether honor allows them to surrender. Neither movie is wholly successful, and given the prismatic structures that both employ—jumping back and forth from the battlefield to the pasts and futures of the people who fought there—it’s hard not to pine for the masterpiece that might’ve resulted had Eastwood combined both halves into one epic whole. Still, it’s admirable that Eastwood chose to spend his substantial Hollywood capital on two films so unrelentingly despairing, and it’s remarkable that a man known for his conservative politics would sign on to helm two stories so critical of military bureaucracy. On the other hand, both Flags and Letters are highly respectful of the actual soldiers, no matter what uniform they wear, and that’s consistent with the ideology Eastwood has expressed throughout his career. He may despise the forces that shape brutal men, but he admires the men themselves.
If The Outlaw Josey Wales represents an Eastwood Western at its most immediately engaging, and if Unforgiven represents Eastwood using the crowd-pleasing elements of a Western as a theme in and of itself, then 1973’s High Plains Drifter is an example of Eastwood perverting the form altogether, just to prove that he can. It’s no secret that every Western Eastwood ever directed was influenced by his time with Sergio Leone, but what’s fascinating about High Plains Drifter is how much it relies on the audience’s expectations of Eastwood’s Leone-created persona. The Man With No Name is supposed to operate under simple, easy-to-understand rules: He’s in the game for himself, but he also has a moral code that means he’ll help those in need, provided he can ensure the situation works out to his best advantage. When Eastwood rides into the small town of Lago in High Plains Drifter, the locals are relieved to find a gunfighter of astonishing skill. They’re looking for protection, and Eastwood seems willing to provide it, at a steep price. But as the story unfolds, it becomes clear that this particular nameless man has a different agenda, and that the townsfolk he’s supposed to be saving aren’t worth the effort. Drifter has its faults (including an ill-advised rape scene), but it mostly works, partly because it’s just so damn nasty, and partly because of the climax. After a hundred minutes of waiting, the “bad guys” finally arrive, and Eastwood’s response is to ride out of town. The movie doesn’t end there, but it may as well have; there’s something perfectly unsettling about a hero who decides that his petitioners don’t deserve to have their prayers answered.
Sex in an Eastwood movie is usually awkward at best, unsavory at worst, and Tightrope is a perfectly horrible representative of the latter. Written and directed by Richard Tuggle (who also wrote Escape From Alcatraz), Tightrope has Eastwood as a New Orleans police detective faced with a rash of dead hookers, and a killer with a tendency to wet himself before arriving at his big moment. Complicating matters further, Eastwood also has to deal with his own yen for prostitutes, and the attachment-free, increasingly kinky sex they provide. And he’s a divorced dad, with two precocious little girls (one of whom, for added ick factor, is played by Eastwood’s own daughter). This setup has potential, but the end result is tedious, psychologically flat, and often inadvertently hilarious. The supposed dark side of lust explored here is never that dark or that lustful, and the hero’s struggle with his needs doesn’t have nearly the depth that all the shots of shadowy streets and grisly murders imply. Eastwood’s typical surprise-sneer doesn’t really work on film as an expression of seduction, and watching him pretend to succumb to a variety of straight-faced come-ons is like watching Sam The Eagle get serviced orally in a back alley. Granted, that’s pretty amusing stuff, but not enough to save this thoroughly miserable tour of the Big Easy.
In general, the ‘80s were a rough decade for Eastwood, creatively. Dirty Harry became a pop-culture icon again thanks to 1983’s Sudden Impact (and thanks to the line “Go ahead, make my day,” which President Reagan appropriated for an anti-tax speech), but a coke-fueled Hollywood was less open to the kind of deliberate genre exercises Eastwood preferred. Eastwood tried to keep up with the times, but a lot of his efforts in front of and behind the camera bordered on the embarrassing. For example, the 1982 high-tech military actioner Firefox and the buddy cop drama The Rookie (released in 1990) were both cliché-ridden muddles, overlong and uninspired. And few movies sum up Eastwood’s ‘80s slump better than City Heat, a stultifying 1984 cop comedy—written by Blake Edwards and directed by Richard Benjamin—that paired Eastwood with the incompatible Burt Reynolds in a frenetic, goofy Prohibition-era scenario that seemed more like a triumph of packaging than anything worth the talents’ time.
Of course, the ‘90s weren’t always kind to Eastwood either. As hard as it is to believe that the director followed up the execrable The Rookie with the magnificent Unforgiven, it’s almost harder to believe that five years after Unforgiven, Eastwood was helming a piece of absolute hackwork like Absolute Power. Eastwood and Richard LaGravenese elevated the runaway bestseller The Bridges Of Madison County into something close to art, but Eastwood and William Goldman had no such luck with airport favorite David Baldacci. Absolute Power’s story of presidential murder is preposterous at best, and Eastwood’s performance as a master thief who knows too much goes beyond tongue-in-cheek to something like self-parody. Eastwood (along with screenwriter Brian Helgeland) also bears responsibility for strangling the movie prospects of modern pulp novelist extraordinaire Michael Connelly in its infancy. The Eastwood-directed 2002 adaptation of Connelly’s Blood Work—about a detective trying to track down the person who killed his heart donor—is so corny and dramatically inert that no one has made films from Connelly’s books since.
Lastly, no discussion of Eastwood’s most embarrassing moments would be complete without a mention of the 1969 musical Paint Your Wagon. But that’s probably best expressed by this clip of Eastwood singing “I Talk To The Trees.”
Eastwood got his start as a B-movie extra and bit player in the mid-’50s, and later graduated to more substantial roles in movie Westerns and on TV. (It’s especially worth tracking down his guest spot on Maverick, where he keeps snidely referring to James Garner’s character as “Mr. Mava-rack.”) Eastwood finally caught his big break in 1959 when he became the co-lead on the TV series Rawhide, about two cattle-drivers having adventures across the plains in the 1800s. The role didn’t exactly make Eastwood a superstar, but it established his screen presence—alternately laconic and quick-tempered—and earned him a ticket to Italy to meet Sergio Leone.
After he became a star—but before he started focusing most of his energies on directing— Eastwood made a number of respectable action movies. The 1968 Western Hang ‘Em High is especially entertaining, working as a more modern version of Budd Boetticher and Randolph Scott’s terse, witty, gripping “Ranown” Westerns. The 1970 World War II/heist hybrid Kelly’s Heroes is a hoot too, even though it suffers from the star-bloat common to its times. But Eastwood’s two best films from his pre-directing era are both Don Siegel specials: the tough-minded cowboy-cop thriller Coogan’s Bluff and the creepy suspense movie The Beguiled, in which Eastwood plays an injured Union soldier whose raw sexuality wreaks havoc on a Louisiana girls’ school.
As a director, Eastwood has made a handful of genre films that have divided critics, but deserve a second look. The 1975 pulp adventure The Eiger Sanction is likeably nutso, with Eastwood playing an art professor (!) who battles ex-Nazis (!!) in between mountaineering (!!!) and going undercover as a homosexual (?). Similarly, 1986’s Heartbreak Ridge is a sublime case of bait-and-switch; pitched as part of Hollywood’s mid-’80s “Let’s reflect on Vietnam” trend, the movie actually stars Eastwood as an over-the-hill Korean War veteran who whips a bunch of self-absorbed pre-Gen-X-ers into shape so they can go kick ass in Grenada. Those two movies represent Eastwood in pure entertainment mode, playing genre tropes for cheap laughs and easy crowd-rousing. The underrated 1999 mystery True Crime is a prime case of late-period Eastwood, less interested in a movie’s plot than in the opportunity it offered him to explore a character. Nowhere is this better exemplified than in True Crime’s “speed zoo” scene, where the journalist Eastwood portrays rushes through a family obligation so he can get back to his deadline. The character behaves abominably, yet the way he makes a blow-off move look charming says a lot about how he’s skated through life to that point.
Eastwood also fits well into straighter genre fare, but sometimes he plays it a bit too straight. He directed and starred in the 1977 action film The Gauntlet, which begins with an interesting premise—he plays a down-on-his-luck cop escorting a prostitute from Las Vegas to Phoenix while running afoul of the mob—but becomes a bit too straightforward for its own good as it goes along, in spite of the sexually charged give-and-take between Eastwood and co-star Sondra Locke. (The two were romantic partners all the time, in a relationship that ended in ugly public accusations and a palimony suit.)
On the flip side, Eastwood’s highly unconventional adaptation of White Hunter Black Heart—Peter Vrietel’s thinly veiled novel about working with John Huston on The African Queen—is worth rediscovering, even if it’s more a fascinating curio than a lost masterpiece. Eastwood plays a hard-living Huston-like director obsessed with taking down an elephant when he should be preparing for his next movie. The setup gives Eastwood a lot of room to explore issues of colonialism and humanity’s destructive relationship with nature. The biggest problem with the beautifully filmed, carefully considered film: Eastwood’s performance stretches in directions he can’t quite reach, as he tries to channel Huston’s larger-than-life spirit.
Still, Eastwood’s failures are rarely dull. Midnight In The Garden Of Good And Evil would be an unfortunate exception, if the adaptation of John Berendt’s non-fiction bestseller weren’t so rich with the atmosphere of Savannah, Georgia. Released in 1997, Midnight fell in the middle of a relatively fallow stretch of Eastwood films from the late ’90s to the early ’00s. From the same period: 2000’s Space Cowboys, which turns what could’ve been—and occasionally is—a pandering tale of aging cowboys into a look at the passing of one generation of American heroism, specifically the one that took us off the Earth for the first time.
The fact that an Academy Award winner like Eastwood would even bother with a movie as programmatic as Space Cowboys speaks as much to his work ethic as to his aesthetic. Eastwood just keeps on working, whether he has an Oscar-caliber script in front of him or not. Last year, everyone assumed Eastwood was destined for a return trip to the Oscar podium with the period crime saga Changeling, which debuted at Cannes and featured the ever-serious Angelina Jolie as a mother fighting City Hall. Instead, Changeling proved to be a sleek-but-routine corrupt-cops tale—and a box-office bomb—while Eastwood drew bigger audiences and more rave reviews with the thick-lined race-relations drama Gran Torino. Some critics rolled their eyes at Gran Torino’s grizzled-old-racist-learns-to-love-the-Hmong plot, and at Eastwood’s stabs at pathos and vulgar comedy. But anyone who’s surveyed Eastwood’s entire career—and has spent as much time with The Eiger Sanction and Heartbreak Ridge as Unforgiven and Million Dollar Baby—should realize that Gran Torino’s bold-plated eccentricities aren’t really an exception. This is Eastwood’s default mode.
After a decade where Eastwood shored up his movie-star credentials at the expense of his auteurist rep, he finally won a pile of Academy Awards and justified his past critical hosannas with this dark, almost primal Western about the weight of responsibility that falls upon those called to kill. Eastwood The Star spends almost two hours avoiding violent action, such that when he erupts, the audience erupts right along with him. Then Eastwood The Director makes those cheers stick in the throat.
2. The Outlaw Josey Wales (1976)
Far less sobering than Unforgiven, this sprawling Western tackles a lot of the same themes in a more rousing, rollicking fashion.
3. The Good, The Bad & The Ugly (1966)
Eastwood’s best film under Sergio Leone’s direction is an epic Western that combines existential cool with zippy style and outlandish characters…
4. Dirty Harry (1971)
…and Eastwood’s best film under Don Siegel’s direction is disturbing for its fascist implications, but only because Siegel and Eastwood make vigilantism look so righteous.
5. Play Misty For Me (1971)
Eastwood’s directorial debut was a departure for him as an actor as well, in that he didn’t wear a hat or carry a gun. Right from the start, Eastwood established that his career wasn’t going to be easy to pigeonhole.