Where does one begin in trying to profile and summarize the works of Clint Eastwood? As an actor, he’s defined himself through his masculinity and everything contradictory that being a man entails. As a director, he’s earned Oscars for his formally tidy style and telling morally conflicted tales. Eastwood the man has a troubled past, redefining his enduring stardom as he has evolved dozens of times over the years since breaking out with Rawhide in 1959. As a star, well, how many actors in Hollywood are actually over six feet tall, have netted over $300 million, and still have carte blanche at a major movie studio?
Fake babies. Dissing Costner. Bad personal relationships. White man’s ideologies. Tried-and-true resolve onscreen as a flawed and compelling hero (most of the time). And how about that time he talked to a chair? Sigh. So much career, so little time. Perhaps for now, we’ll start where he did – with acting. Welcome to Clint’s 10 best performances. A brief summary of a legendary career, as it were. Icon. Agitator. Old softy and dude with attitude. You can pooh-pooh his more reckless incidents or express jealousy for the anarchy he got away with. But love him or hate him, the man is a living legend. And at 87 years of age, he’s still churning out the hits (just more often behind camera than not these days).
Quick rules? No TV, so apologies to any Rawhide diehards. And one entry per franchise, or else there’d be a number of Dirty Harries running wild with Smith & Wessons causing chaos. Otherwise, we hope this list makes your day, you lucky punks. Anyways, crack a Pabst, and please don’t shoot me.
10. Coogan’s Bluff (1968)
Think the Clint archetype, but in New York City.
Save your Pace salsa jokes. Coogan’s Bluff just works, and does wonders to prove the durability of Eastwood’s gritted-teeth caricature. It even shows faint signs of levity in Eastwood’s steely demeanor. Ironically, it’s a “damn hippies” sort of procedural, and Clint slides through like a cobra amidst flowers. But honestly, this is just fun-as-hell pulp.
The fish-out-of-water film is the stuff of hackwork nowadays, but Eastwood did it with such confidence. You’ve seen the urban drug avenger, but with a way-out-West cowboy in the thick of it? Walt Coogan’s the name, and he’s the Arizona lawman dispatched to New York City (one complete with pool hall fights, happenin’ LSD weirdness, make-out sessions, and all sorts of freaks trying to kill Coogan). The almost clichéd work of Eastwood feels like it really can fit into any movie here. Clint’s a fighter, a lover, a cowboy, a cool guy, and above all, a star.
Who’s Directing: Well, well, well, if it isn’t Don Siegel. This would be the first of five films Siegel made with Eastwood, and Siegel would later become his directing mentor. Best buds, these two.
Essential Eastwood: Apologies for the second-hand YouTube quality here, but in the year of Bullitt, Coogan’s final bike chase is criminally underseen. Proves that Clint just looked great in action.
09. Every Which Way but Loose (1978)
For the sake of honesty, we’ll just say it now – this movie’s dumb as a rock. It’s that buddy actioner with Eastwood and a beer-swilling orangutan named Clyde. Perhaps you’ve seen the stills of Clyde giving the finger online? Share it via text if you get the chance! The sequel’s even sillier, and it gave us a Ray Charles and Clint Eastwood duet about beer. But damn it, we love Every Which Way but Loose anyhow and the way in which Clint pals around with his co-star in self-effacing fashion. It’s a farce with its brow hung low as Eastwood stars as Philo, the trucker/brawler just a’ drinkin’ and a’ punchin’ his way through the American West.
While you can guess the general beats – orangutan makes a silly, Philo bops other boys in bars – the overall mood is so easygoing. Clyde socks Nazis (suck it, alt-right), Ruth Gordon pisses and moans about Oreos, and Eastwood knocks ‘em dead in fist fights with his girl and his ape by his side. Every studio passed on this, but Eastwood thought it would be fun in the wake of Smokey and the Bandit and other good, ol’ boy comedies. Adjusted for inflation, this is still Clint’s biggest hit – over $500 million in 2018 numbers.
Who’s Directing: James Fargo got his start as an assistant director on TV movies before eventually graduating to his first feature film, The Enforcer (the third Harry Callahan film). Perhaps it’s to Fargo’s credit that Eastwood has been quoted as saying that Clyde (Manis, in real life) was the most natural actor he’s ever worked with. That takes good direction and guidance, one reckons.
Essential Eastwood: Oh, Clyde steals the show for sure. But if you’ll pardon the expression, Eastwood’s a helluva second banana.
08. Where Eagles Dare (1968)
Brian G. Hutton’s spectacle holds up in a way best described through onomatopoeia, Where Eagles Dare is boffo kablammo! It’s an insane, stunt-filled war epic (one that Tarantino willfully riffed upon for his Inglourious Basterds). And Eastwood is simply B.A.D. ass in it, but he does it in a minor key. Clint kills, early and often, but with a modest intensity. He arguably disappears into it, acting as a perfect utility for action filmmaking, a believable face and presence for larger-than-life set pieces and scenarios. Next to Richard Burton’s exorbitant theatrics and Brian Hutton’s arsenal of stunt and effects men, Eastwood just slides into this World War II event role with spy-like gamesmanship.
Who’s Directing: Brian G. Hutton would reunite with Eastwood a mere two years later for Kelly’s Heroes. Hutton got Eastwood to do his own stunts on this sucker.
Essential Eastwood: Look at Eastwood, just hanging back. Taking it in. And doing that thing where the quiet dude might be the most intimidating one in the room. Even with hype from British forces, Eastwood just keeps it cool. That, right there, is presence. And it’s a testament to his performance when so many hyperbolic explosions and so much action occurs, yet his demeanor feels hypnotic and almost like a reprieve.
07. The Outlaw Josey Wales (1976)
The film school kids are still dueling over Josey Wales’ perceived left- and right-wing politics. In the wake of Saigon, Josey Wales focused on post-war trauma, Native reparations, and deep resentment for the government that screams … well, Eastwood would prefer you decide for yourself. Sneaky Pete. While known as conservative in real life, his films tend to be best read as moral fables — extended thought scenarios that look less to make a single statement on something and instead reflect on extraordinary circumstances or reality-suggested troubles. (By Eastwood’s own admission in documentaries, any bias or political reads were incidental and only help to strike up conversations.)
Josey Wales had soul, regret, and a conscience, and all he was looking for was closure (read: revenge) after his family’s massacred. The Missouri farmer wanted action against the Union men that killed his family. It a harsh premise, and Clint was rarely as good at selling those kinds of dilemmas as he is here. Pale Rider, High Plains Drifter, and especially Unforgiven play in the same turf, but rarely has he been this intense and satisfying and just plain tough in the role.
Who’s Directing: This was Eastwood’s fifth directorial effort and perhaps the earliest signs of philosophical life in his Westerns. But here’s the crazy story: Eastwood replaced the original director and writer, Philip Kaufman, at the 11th hour, prompting the DGA to create an “Eastwood Rule” banning actors from taking over productions. All over an alleged boy’s fight for the affections of co-star Sondra Locke. Ugh, fellas.
Essential Eastwood: Remember how much John Wayne hated Native Americans? Well, Eastwood, and by virtue Josey Wales, had more modern, complicated, and compelling drives to interact with Native Americans.
06. The Beguiled (1971)
Eastwood, the onscreen manipulator of women. 1971 was a curious year. Eastwood doubled down as a clueless DJ in his directorial debut, Play Misty for Me, and The Beguiled saw Eastwood as a “blue belly” Union deserter and wolf in the chicken coop that is a Confederate girls boarding school. But while the former falls into the problematic at times, The Beguiled still flies as a nervy work of Southern gothic and haunted, perverse eroticism. And Clint was up to the task of being the gross, pathetic, and cunning McBurney in one of his least remembered, least likable, and most underappreciated roles. And boy, does he get what’s coming to him. It’s a balancing act, as Eastwood nails broken-dog pity, womanizing evil, and deserving amputation that leaves him in agony. It’s a familiar sort of evil for the ages.
Who’s Directing: Clint and Don Siegel, at it again. Apparently, Eastwood was interested in the novel for some time, as he was fascinated by the source’s notions of male desire to castrate female power. Curious given his macho man M.O., no?
Essential Eastwood: Before the Coppola remake, a colleague reminded me of the “old enough for kisses” line, and naturally, I retched. Hey, if that’s not effective villainy, I don’t know what is.
05. Sudden Impact (1983)
Oh, you could muster up some false sense of outrage thanks to this listicle vaunting Sudden Impact over the original Dirty Harry, but the thing is Eastwood’s 1983 entry into his long-standing franchise is hands-down the most entertaining and curiously re-watchable entry. Sure, they’re all rabid, entertaining, and at times affably corny. But Sudden Impact has some of the best one-liners, an almost (in the loosest sense of the term almost) feminist plot, and Eastwood’s just having a time here. The movie works as both a hard-boiled cop procedural like the originals, but even more so; it’s almost like a surreal parody. The Gargoyle sunglasses. The fact that he threatens a mobster into having a heart attack. The almost erotic enthusiasm for Smith & Wesson. The car chase with the old folks. And the seemingly apologetic consideration of a villain that’s also a battered woman — Harry never showed paused before. It’s like Eastwood’s having a good time being both reckless and mindful with his co-creation. He shakes things up, perfecting Callahan on the fly. For our money, this is the dirtiest (and best) Harry.
Who’s Directing: Funny how Clint Eastwood got some of Clint Eastwood’s best performances, right? The man once likened his return to Callahan to meeting an old friend and getting comfortable with pushing things around a little. No wonder he lets that weird “no man puts ketchup on a hot dog” joke in here.
Essential Eastwood: Speaking of food? Damn, you do not mess with Harry Callahan’s sugar.
04. Million Dollar Baby (2004)
The guerilla marketing and sneak-attack release really protected this special movie. What starts as a boxing yarn morphs into a deeply tragic tale of life, death, and the hard choices we’re stuck with in between. At this point, the twist is well-known enough that we must discuss it. Because Eastwood crafted a deeply emotional film built on his aging fight trainer’s struggles to do the right things.
To train a backwoods girl into putting her dukes up, despite his aged sexism and fear of failure. To commit to protecting this girl after a terrible accident leaves her quadriplegic and him riddled with guilt. And ultimately, Eastwood must decide whether to euthanize this young boxer after she specifically asks for it – but he may not be up to the task. Million Dollar Baby is a new classic, balanced and deep, and Eastwood wears the film on his tired-but-still-able back to perfection.
Who’s Directing: Eastwood signed onto Baby after it languished in development hell for years, but only if he could star and direct. Eastwood filmed the project in a mere 40 days, turned a huge profit (after Warner balked over budget), and netted Oscars for Hilary Swank, Morgan Freeman, and himself (for directing).
Essential Eastwood: “Macushla. Means, ‘My darling. My blood.’”
03. The Good, the Bad and the Ugly (1966)
Fun fact: my dad’s gone on about this film and seeing it among friends and classmates in ’66. Sure enough, they all were so riled and inspired by director Sergio Leone’s theatrics and Eastwood’s hard-ass look that my dad and his pals were smoking cigarillos pretty much seconds after the film ended. Hilarious, given that Eastwood himself hated smoking.
But that’s what happens when you create one of the most iconic Western, and film, roles of all time. You know the Ennio Morricone sounds, the lustrously shot landscapes, and the brooding, haunting, and hypnotic look of Eastwood in The Good, the Bad and the Ugly. That Blondie was Eastwood’s breakout creation, and to this day, Blondie defines cowboy cool with his glint, his poncho, and his square-jawed patience. With his contemplative presence and agonizing struggle to survive in the sun-scorched Southwest, Eastwood casts a dusty, grizzled spell over all who cross his path. He’s a tough mother trying to be good or bad or whatever all that meant during the Civil War.
Who’s Directing: Good day, Sergio Leone. The iconic Italian helmer apparently had trouble luring Eastwood to this movie. Who knew? Eastwood was worried about being upstaged by Tuco, and he refused to film unless he got more money at points – but in the end, who’s the guy on all the Blu-Ray covers?
Essential Eastwood: You have 10 minutes to savor the absurd faces of Eastwood? (Not to mention Lee Van Cleef and Eli Wallach’s, for that matter?). Of course you do, padre!
02. The Bridges of Madison County (1995)
Clint’s never been a romantic. In Coogan’s Bluff, he beds a girl by yanking her into a bathtub. In all of Eastwood’s Sondra Locke films, the two are constantly at odds, often slow to fall in love. Girls, right? You can practically hear the Gran Torino–esque grumble at the thought of Clint having to be vulnerable. A man’s man. That’s his rep.
At least it was until he broke it all down, took off all the weapons, and fell madly in love with Meryl Streep in The Bridges of Madison County. This is an affair to remember — a summer breeze with passion in its core. And it’s an Eastwood vehicle that feels entirely left field given his M.O., and he comes out of it almost beaten and broken (but ultimately accepting). It’s a love that cannot be, and Eastwood’s Robert Kincaid knows it. So enjoy a little bit of love when you can in your life, before other commitments take hold. You will believe the man with the crazy kill-count can be broken come the end! Eastwood rocks the sensitive photographer vibe with everything he’s got, and it’s some of the best and most sincere acting of his entire career. And frankly, one can’t help but fawn at the guy’s tall, handsome qualities.
Who’s Directing: Clint Eastwood, allowing himself to cry in the rain on camera. One wonders how many men were fuming over this in 1995?
Essential Eastwood: Oh, here come the waterworks. All that killin’, all that cussin’, all that fightin’, and Eastwood’s a lone, scared man just standing in the rain. Yes, that sounds a little like bunk when you say it aloud, but for goodness sakes, Clint sold it!
01. Unforgiven (1992)
Few people saw the exceptional craft, care, and performance of Unforgiven coming. In a feisty career that parades a bevy of beautiful cowboy roles, Eastwood’s Bill Munny is his finest work as both an actor and director. It’s a sterling, unfussy, and deeply affecting drama from a seemingly self-aware and slightly confessional Eastwood. Wildly scary and deeply forlorn, Munny was the perfect vehicle for a well-seasoned Eastwood. It was the right time for this story. Maybe he felt guilt for past sins, reflecting on personal demons, or shame at his aging. Whatever the case, this is a master’s class in blue-cowboy pathos that grows stronger with each passing year. It’s not about an angry gunman, but about one finally coming to terms with the terrible things he’s done – and maybe even accepting of how good he was/is at being a real son of a bitch.
Clint was in his 60s, looking a little less exciting to his native Warner by the day, and his commercial luster had waned after flops like The Rookie, White Hunter, Black Heart, and Pink Cadillac. It was time to change, to reveal himself more than he thought he could, and Eastwood dug deep on this one. Bill Munny has a full arc that shoots from the heart, and he never quite lands where you think he will. From Eastwood struggling to shoot cans, to him trying his damndest to sidle up and do right with women, to his perhaps inevitable failures, he gives a terse, brilliant performance. One for the ages.
Who’s Directing: Clint at it again, nabbing his first nominations for actor and director and a win for the latter. His direction is assured, complicated stuff, and Unforgiven has gone on to be a staple in Eastwood’s long and lustrous career. Sure, the Academy loves actor-directors, but let’s say you’re looking at Ordinary People, Dances with Wolves, and Unforgiven on the shelf: which one are you gonna watch first? Damn right, it’s Unforgiven.
Essential Eastwood: It’s an image as old as the movies – cowboys ‘round the fire, commiserating and so forth. But it’s what Eastwood does with this moment and how Munny confesses to sin, guilt, and the open acknowledgment of what a mean machine he’s spent his life being – one people assumed would kill you as soon as you look at him funny. Eastwood’s rarely been this sparse, bare, and open in his acting and directing. Bill Munny is a man of many contradictions, and he gives a portrait of tragic depth. Eastwood broke new ground as a performer and director here while nearly reinventing and honestly reflecting on the troubles of a genre he helped popularize in this very moment. This is maximum Clint.