The 25 Best Clint Eastwood Movies, Ranked (2024)

Eastwood was 88 when this slow-burn south-of-the-border thriller that he directed and starred in hit theaters. All of that mileage informs his portrayal of Earl Stone—a cash-strapped Korean War vet who unwittingly takes a job making deliveries to Mexico for one of the cartels. The premise of a geezer drug mule is hard to top, and Eastwood gives his character convincing shadings of loneliness and grace as he starts breaking bad. He also shows you how much fun Earl’s having behind the wheel as he sings along with the radio. Bradley Cooper plays the DEA agent shadowing the unlikely courier, but this is Eastwood’s show all the way. It’s hard to think of another actor with the same reserves of good will and charm to pull this off and not make it feel like Grumpy Old Drug Traffickers.

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Before Hollywood got too deep into the sequel business, this follow-up to 1971’s hot-button vigilante flick Dirty Harry proved it was possible to go to the well more than once if your main character was as iconic as Eastwood’s shoot-first-ask-questions-later detective Harry Callahan. Thanks to a screenplay by resident Tinseltown gun lover John Milius, Magnum Force is a brisk and brutal conspiracy thriller about rogue cops knocking off criminals who manage to skirt punishment. The irony isn’t lost on Harry—a cop known for taking the law into his own hands who now has to track down and bust a bunch of cops who take the law into their own hands. Was the movie penance for the violent sins of Dirty Harry? Don’t overthink it. He’s still Harry, and he’s still plenty dirty.

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A fish-out-of-water cop thriller with Eastwood as the Stetson-wearing fish. Directed by his mentor and longtime collaborator Don Siegel, this was the actor’s first non-western leading role. Eastwood plays an Arizona deputy sheriff who’s sent to New York City to bring a fugitive (Don Stroud) back home. The movie’s “hayseed in the rotting Big Apple” shtick leads to some gloriously groovy depictions of hippie amorality, and Eastwood’s growing exasperation from Noo Yawkers asking if he’s from Texas is priceless. It also leads to a fantastic brawl in a pool hall. Coogan’s Bluff feels like a violent dress rehearsal of sorts for Eastwood and Siegel’s Dirty Harry reunion three years later.

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The poster for this vengeance oater directed by journeyman Ted Post says it all: “The hanging was the best show in town. But they made two mistakes. They hung the wrong man and they didn’t finish the job.” Hang ’Em High wasn’t Eastwood’s first western, but it was his first Hollywood western. And while it doesn’t have the same operatic grandeur as Sergio Leone’s Man with No Name trilogy, it does have one hell of a central set piece as Eastwood’s wrongly accused former lawman makes a last-minute escape from the gallows. Plus, it’s got a veritable who’s who of great character actors from the era who all add spice to the stew: Bruce Dern, Pat Hingle, Ed Begley, Ben Johnson, L.Q. Jones, and Alan Hale Jr. (aka the Skipper from Gilligan’s Island). Yes, this is yet another film where Eastwood was hired to be judge, jury, and executioner. But at this early juncture, that formula hadn’t hardened into a cliché yet.

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Originally, Eastwood wasn’t going to appear in this haunting and underrated cat-and-mouse road movie. He only had plans to direct it. But when Kevin Costner said he’d only play the lead if he got to share the screen with the legend, Eastwood relented. It’s a good thing he did, too. Eastwood plays a sympathetic Texas Ranger pursuing a violent escaped convict (Costner) and the eight-year-old Jehovah’s Witness he’s taken hostage across the tumbleweed back roads of the American Southwest. The always-welcome presence of Laura Dern as a headstrong criminologist nicely sands down some of the movie’s more macho edges. Still, it’s T.J. Lowther as Costner’s pint-sized captive who stands out as the film’s MVP.

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I’m sure many of you will disagree with this lurid Dirty Harry sequel making the cut, but hey, I saw this movie at the perfect age—I was 14 and Clint was my guy—and it’s stuck with me. I’ve seen it several times since then, and I’ll never stop going to bat for it. Sondra Locke plays a rape survivor with PTSD who’s working her way down the list of skeezy beach bums who assaulted her and her younger sister years earlier. Meanwhile, Harry starts dating her before realizing she’s a payback killer. Locke is convincingly cold and haunted, the run-down beach-town setting is evocatively bleak, and the violence is brutal and matter-of-fact. At this point in the Harry cycle (this is the fourth entry), Eastwood knows exactly which buttons to push for fans. This is a sick, nihilistic revenge flick that delivers the grind-house goods. Forget what you’ve heard and give it a shot.

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At a time when a new generation of maverick auteurs was taking over Hollywood, Eastwood popped up in a star-studded World Waw II adventure that couldn’t have been more old-school and square if it tried. Yet Where Eagles Dare is a blast. At the time, Richard Burton was technically considered the main attraction here—and he’s fine (if a bit sweaty and hungover looking). But as his lieutenant on a behind-enemy-lines mission to rescue an American general being held in a Nazi castle, Eastwood shows Burton how to do more with less.

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“Get off my lawn!” Yup, we’re deep into Clint’s late period of crusty curmudgeons here. Gran Torino is arguably Eastwood’s second-best performance of the 2000s after Million Dollar Baby. As Walt Kowalski, a beer-drinking Korean War vet and retired auto worker who’s fed up with the influx of Asian, Latino, and Black families moving into his neighborhood, the actor goes full MAGA. But there’s a soft, chewy center beneath his hard, outer shell. Walt catches an Asian teenager trying to steal his beloved 1972 Ford Gran Torino Sportsroof. It turns out the kid was bullied into it by a local gang. Walt stands up to the toughs, forms an unlikely bond with the kid, and becomes less of a racist. It’s not a subtle movie by any stretch, but Eastwood sells the hell out of it. Have some tissues nearby.

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Aside from his pair of WTF orangutan comedies, Every Which Way But Loose and Any Which Way You Can, this may be the weirdest movie that Eastwood was ever a part of. The actor plays a wounded Union soldier during the Civil War who finds refuge at remote girls’ boarding school in the South. Nothing weird about that. But then director Don Siegel jerks the steering wheel into Misery territory, as the students all fall obsessively, jealously in love with their patient. The Beguiled feels like an exploitation fever dream. It’s also proof that Eastwood was up for taking massive risks at the height of his stardom. Sofia Coppola remade this one with Kirsten Dunst and Nicole Kidman in 2017. Skip it and watch the kinky, twisted original instead.

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Before Michael Cimino directed 1979’s Best Picture winner, The Deer Hunter, and before he would nearly bring a studio to its financial knees with 1980’s Heaven’s Gate, he would make his debut behind the camera with this all-too-forgotten buddy-heist thriller. Eastwood and a very fresh-faced Jeff Bridges play a pair of bank robbers on the run in Montana’s Big Sky Country. Bridges, who would earn his first Oscar nod for this, manages to coax an unexpected comic breeziness from his stone-faced costar. The two spark off one another like flint and steel. The “one-last-job” movie is one of the most cliché-filled subgenres. Thunderbolt and Lightfoot skirts all of them.

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For the most part, Eastwood steered clear of westerns in the ’80s. This was the lone exception … and it’s terrific. A tiny prospecting town is being terrorized and shaken down by a powerful mining company. Then a mysterious preacher arrives (take a wild guess who) and delivers them from evil. Eastwood turns out to be a man of peace in name only, relying on his trusty sidearm more than the good book. At times, Pale Rider feels like an unofficial sequel to 1973’s High Plains Drifter. And while it doesn’t try to reinvent the (wagon) wheel, what it does it does masterfully.

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Fifteen years before Shawshank, we got this drum-tight Don Siegel prison-escape thriller. I was ten when Alcatraz came out, and I thought it was the coolest movie in the world. Good news: It holds up. Eastwood plays Frank Morris, a stoic inmate at the infamous island prison who devises a plan with two of his fellow cons to break out and get off the Rock. Patrick McGoohan is indelibly menacing as the crooked, sadistic warden while Eastwood dials back his performance to let the suspenseful, slow-boiling, nearly silent escape be the star. I may have to watch this one again tonight.

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There are two films on this list that Eastwood directed but did not appear in. This is the first. A lifelong jazz aficionado, Eastwood once told me about seeing see sax god Charlie Parker play live. With this heartfelt, Palme d’Or–winning Parker biopic, he got his chance to return the favor. Forest Whitaker summons angels and demons as the insanely talented bebop legend who turned his troubles into sublime music even as heroin addiction ate him alive until he overdosed at age 34. This belongs right up there with Young Man with a Horn, Round Midnight, and Whiplash on anyone’s list of the greatest jazz movies ever made.

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Surreal and sensational, this bizarro western feels like Eastwood’s riff on one of Sergio Leone’s revisionist oaters with a dash of religio-mysticism thrown in to keep things weird. As in Pale Rider, Clint comes to the rescue of a frontier town full of cowards and pushovers and shows them how to stand up to outlaws. Except this time around, he uses psych-ops instead of a six-shooter (although he uses that too), literally painting the town red like a haunted-house version of hell. This was the first western that Eastwood directed, and it feels more Jodorowsky than John Ford. Clint is having a gas here experimenting with the genre and pushing it in strange new directions. For a deeper dive on High Plains Drifter, check out this 2020 essay.

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This is where the Eastwood origin story truly begins. During his hiatus from the TV show Rawhide, he got an offer to play the lead in an Italian western. He figured if it was awful no one in America would ever see it. Needless to say, it wasn’t awful and everyone saw it, turning Eastwood in an international superstar overnight. Director Sergio Leone adapts Akira Kurosawa’s Yojimbo into an Old West showdown between two warring clans, with a no-named drifter playing both sides against the other. Chomping on a cheroot and squinting in the Mediterranean sun, a silver-screen legend is born.

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Yup, this sequel to A Fistful of Dollars is even better than the original. Not by much, though. Director Sergio Leone’s style comes into sharper focus in this middle chapter of the Man With No Name trilogy—the supertight close-ups, the operatic grandeur, the insane Morricone score. Eastwood and the even squintier Lee Van Cleef play rival gunslingers out to collect a bounty on the head of the ruthless El Indio (Gian Maria Volante). There is literally nothing about this movie that is not fucking amazing.

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For his directorial debut, Eastwood wisely steered clear of dusty horse operas and instead delivered this tense workout of a thriller about a late-night jazz-radio DJ with a regular caller who turns out to be a bit too much of a fan. Jessica Walter (in a sweet shag hairdo!) is terrifyingly unhinged as the obsessed stalker who goes Fatal Attraction on Clint after a one-night stand. As for the vinyl-spinning Eastwood, he is the definition of hep-cat cool, even as he trafficks in sorely outdated sexual politics.

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Picking back up from Bird at number 13, this is the other “only directed by” Eastwood film on the list. But what a film! As a Bostonian, I had some pretty serious concerns about this adaptation of Dennis Lehane’s best seller before it came out. Not only how Sean Penn, Tim Robbins, and Kevin Bacon would mangle the local dialect but also about how a director as laid-back as Eastwood would handle the film’s emotionally incendiary Irish Catholic themes of crime and sin. Turns out, I had no reason to worry. This is as good—and as powerful—as mainstream Hollywood filmmaking gets.

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Okay, we are now officially in the first-class, filet mignon section of this list. You give me any movie that pairs Eastwood and Morgan Freeman and I say, “Take my money!” Eastwood captures the sweat and spit buckets and the skid-row desperation of the fighter’s gym and gives it a sense of elevated grace. Hilary Swank rightly earned her second Oscar in this devastating drama about a female boxer who breaks down a couple of old L.A. gym rats to take her under their wing and train her. I’m a sucker for Eastwood in this mode—world-weary, skeptical, and defeated. At least until Swank’s Maggie Fitzgerald comes along. The third act is a heartbreaker, but everyone onscreen is doing god-level work. Million Dollar Baby would earn Eastwood a pair of Academy Awards, for Best Director and Best Picture.

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Even if don’t consider yourself to be the target demo for an adaptation of Robert James Waller’s schmaltzy love story, give this a shot. It’s fantastic. Just ask your mom. It’s also one of the most satisfying big-screen romances of the past 30 years. Eastwood stars as a Life magazine photographer on assignment to shoot Iowa’s charming covered bridges. While there he meets Meryl Streep’s Francesca, a married Italian housewife whose husband and son are out of town. A connection is made, and as much as they try to tamp down their feelings, they can’t. But they also know that they will soon have to go their separate ways. While the two lead actors may seem like oil and water, their chemistry is subtle, palpable and deeply moving. Try to resist it all you want, but The Bridges of Madison County will make you swoon.

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