10. “Gran Torino” (2008)
A movie that ostensibly finds Eastwood taking the piss out of his macho onscreen persona (if there was an Academy Award for Best Growling…), “Gran Torino” looks on the surface to be a straightforward “racist-guy-learns-to-love” film, but turns out be both more simplistic and more complicated. Eastwood’s character is less of a racist than an all-round equal-opportunity asshole, and even as he befriends the foreign neighbors who initially drive him bananas, he doesn’t suddenly stop using racial slurs or change much of his attitude. They earn his respect and in turn he earns theirs. To its credit, the film very carefully navigates some pretty difficult racial and political territory without ever going to the pulpit, and the script earns its emotional punch. That said, this is B-level material for Eastwood (it’s essentially a smarter-than-usual vengeance pic) that also veers into the kind of weepy ending that seems to be his specialty, particularly in his late-career films. It’s not perfect, but is certainly far more enjoyable and insightful than you might expect, and though hampered by some ropey acting from the supporting cast, “Gran Torino” earns its stripes and takes some unexpected, refreshing detours along the way.
9. “Bronco Billy” (1980)
Though famously an underperformer at the box office, Eastwood’s gentle comedy “Bronco Billy” is such a sweet-natured shaggy dog story that it’s hard to account for it not finding an audience. Perhaps its easygoing charm felt out of step with post-Watergate times: it’s lacks any sense of paranoia. Detailing the loopy struggles of a ramshackle traveling circus comprised of a bunch of ex-cons who cluster around trick shooter Billy (Eastwood) as an extended family, the film’s only really mishandled element is the romance. And even then, it’s not so much that Sondra Locke is bad as the spoiled heiress who falls in with the troupe out of desperation —it’s that her character is poorly written and changes from rapacious snob to doe-eyed rootin’ tootin’ cowgirl sidekick on a dime. But mostly, “Bronco Billy” coasts by on its lighthearted idealism, with the circus and the vision of the Old West it espouses with such old-fashioned decency coming to stand for the very idea of self-creation and self-fulfillment in a grasping, noisy, modern world. It feels atypical, making it even more interesting that Eastwood has such a soft spot for it: he once said “If, as a film director, I ever wanted to say something, you’ll find it in “Bronco Billy’.”
8. “Million Dollar Baby” (2004)
We were all a bit surprised when “Clint Eastwood’s female boxer movie” actually turned out to be “Clint Eastwood’s euthanasia movie,” but it wasn’t just surprise that buoyed it along to the Oscars. His 2004 Best Picture tackles a deeply off-putting subject in a sensitive and intelligent way, smuggling in its tough message under the guise of a rags-to-riches, beating-the-odds boxing movie. That said, there are familiar Eastwood themes of singleminded endeavor, duty and Catholic guilt running throughout. Frankie Dunn (Eastwood), trainer and boxing gym owner, reluctantly accepts the challenge of training the stubbornly insistent Maggie Fitzgerald (Hilary Swank, scoring her second Oscar in five years) to be a fight champion, overseen by Morgan Freeman’s aging pugilist (and voice of Frankie’s conscience). But the familiar rhythms of the grudging-mutual-respect arc and the underdog-rising story come to an abrupt stop midway, when Maggie is grievously injured by an unscrupulous opponent, and the central relationship becomes one of almost parental love, grief and desperation. It’s unabashedly earnest, but with its steady, humanist intelligence and its fine performances (Swank and Freeman get a lot of the notices, but it should be remembered as one of Eastwood’s own best late-career turns), this is also a consummately well-crafted and affecting film.
7. “Mystic River” (2003)
For a while around the turn of the millennium, it seemed like Eastwood’s directorial career might be going gently into the good night, as a succession of rather toothless thrillers and underwhelming bestseller adaptations had eroded any remaining idea of him as a firebrand. That changed with “Mystic River,” which is as ferocious a film in its way as this most restrained of filmmakers has ever made —for better, and in some heightened moments, for worse. Based on the novel by Dennis Lehane (who’s built an empire on gritty morality tales of working-class Bostonians blurring the line between right and wrong) and adapted capably by Brian Helgeland, the film brings together three reliable actors: Sean Penn, who went FTW with Oscar; Tim Robbins, pocketing an Oscar as well; and meme-spawning everyman Kevin Bacon. Their intertwined stories, plus a murder investigation form the crux of an expansive Boston-set boiler, steeped in a deeply Eastwoodian idea of vengeance and the inescapable sins of the past. Marcia Gay Harden and Laura Linney also deliver terrific if brief performances, and even if not everything coheres quite as it should, still there’s a great deal more to the film than Penn’s anguished howl… though as anguished howls go, it’s up there with the best.
6. “Bird” (1988)
Considering his rep as a tough guy, and more recently as a right-leaning Republican tired of this “pussy generation,” it’s remarkable that one of the more sensitive musical biopics, a genre full of disastrous attempts to over-explain legends, should come from Eastwood. But the noted jazz enthusiast (he composed jazz-inflected scores for several of his films) delivered a passion project with Charlie Parker biopic “Bird,” and his love for the music and the man shines through. Forest Whitaker, in one of his earliest high profile roles, is sensationally good, picking up a Best Actor award at Cannes, with the ever-underrated Diane Venora easily his match as Parker’s last wife Chan. It doesn’t shy away from the darker aspects of Parker’s life either (he was addicted to heroin for the majority of his adult life), but still manages to keep on the right side of cliché. There are indulgences in the film’s loose structure, which while appropriately freeform renders the film overlong, Still, Eastwood’s love of the music is undeniable (he and music coordinator Lennie Niehaus isolated Parker’s playing from original recordings, then mixed them with contemporary musicians, paying tribute to the man while keeping the music fresh) and infectious.
5. “Pale Rider” (1985)
Eastwood’s work throughout the 1980s never earned the acclaim of his ’70s output, nor his (first) renaissance period in the early ’90s. But the ’80s represented an important turning point, and “Pale Rider” is one of Eastwood’s more directly, if also slightly subtle, political films: it’s a movie forged in the exact moment that saw Ronald Reagan begin his second term as president, and which saw the consumerist ’80s reach their midpoint zenith. The film’s plot plays like a capitalistic take on Akira Kurosawa’s “Seven Samurai“: a small settlement of gold miners in the California foothills call upon a mysterious, unnamed stranger to protect them from the tyranny of corrupt authorities. Eastwood plays the Unnamed Stranger, a preacher/gunslinger and a symbol of honest American values in the middle of the rampantly consumerist and acquisitive ’80s. This thematic heft helps distract from the film’s sometimes sloppy scripting, and Eastwood’s often overlooked gift for crafting evocative imagery —including a unique take on “The Searchers‘” iconic doorway-framing shot which uses a darkened interior and lit exterior as a potent visual metaphor for his character’s shrouded past and chance at eventual redemption— makes this one of his most striking, sturdy Westerns.
4. “The Outlaw Josey Wales” (1976)
Possibly Eastwood’s essential anti-war Western, using the safe space of the past to express the disillusioned mood of the post-Vietnam era, “The Outlaw Josey Wales” is however no peace-loving, pacifist tale. Wales (Eastwood) is the epitome of the cool, skilled gunfighter character, an outlaw because of his vendetta against the corrupt Union Army “Red-Legs” who brutally murdered his wife and child. Wales joins a Confederate guerrilla group, spills a lot of Union blood and inspires a bounty on his head in the process. Against all odds, he ends up accumulating a diverse band of strangers to serve as his de facto family, including an older Cherokee (Chief Dan George), a young Navajo woman, a gun-toting granny and an innocent-yet-sexy hippie chick. It feels like classic Eastwood, but it’s a twist on the classic Western, with the genre conventions put to use at times and subverted at others, all the better to tell this particularly resonant story. Ultimately, the audience comes away with a sense of the moral corruption of war, the importance of family (traditional or not), and the power of the individual in the face of institutional untrustworthiness. Oh, and the iconic motto, “Dyin’ ain’t much of a livin’, boy.”
3. “High Plains Drifter” (1973)
The most frequently and most bafflingly overlooked Western in Eastwood’s catalogue, and also arguably his most interesting, “High Plains Drifter” is almost a genre hybrid, or certainly rewards reading as a horror Western, rather than just a straight-up gunslinger tale. Eastwood plays The Stranger, who defends a small mining town against a bunch of bloodthirsty villains, which is typical Western fare (and indeed he’d return to it in a decade with “Pale Rider”). But the movie has a surprisingly raw edge, featuring strong violence and sexuality, and yet the actual genius of “High Plains Drifter” lies in its supernatural overtones, replete with numerous biblical references. The town the Stranger defends is initially called Lago, but is re-titled, in a swath of red paint, as Hell, and there’s a nasty dwarf, played memorably by character actor Billy Curtis, named Mordecai. Visually and thematically indebted to Sergio Leone and Don Siegel (whose names appear on tombstones in a graveyard sequence in the film), and with a deeply strange tone that’s akin to a modern-day revenge epic (Quentin Tarantino borrowed these elements heavily for the second half of “Kill Bill“) meeting a ghost story. A career highlight that deserves far more attention than it gets.
2. “A Perfect World” (1993)
Coming off probably the greatest achievement of his acting and directing career, nobody expected Eastwood to match “Unforgiven” the next time out at bat. But though no one really saw him do it, he came incredibly close with “A Perfect World.” Teaming for the first and only time with Kevin Costner (at the time easily the biggest movie star in the world), Eastwood originally intended to only direct, but was persuaded by Costner to take on the supporting role of Texas Ranger Red Garnett, who pursues escaped convict Butch Haynes (Costner) after he takes an eight-year-old Jehovah’s Witness boy hostage. Eastwood’s turn is solid, but the performances he draws from child actor TJ Lowther and from Costner are outstanding. At close to two-and-a-half hours, it’s a touch too long, but as Eastwood’s most lyrical film since “Honky Tonk Man,” which it vaguely recalls in its road movie, intergenerational vibe, you’d be reluctant to cut a single one of its quasi Malick-ian frames. Its deep, desperate melancholy and the unexpected humor of the script mean that, while it may never quite get its due, this film remains Eastwood’s greatest hidden gem.
1. “Unforgiven” (1992)
It’s been twenty-four years since he last tackled the genre, but then, if we’d made “Unforgiven,” we’re not sure we’d have anything left to say about the Western either. Almost inarguably the crowning achievement of Eastwood’s directorial career, the revisionist film had been floating around the industry for years, with the director eventually buying up the rights but deciding to wait until he was old enough to pull off the lead role. His patience paid off — no one else would have brought the baggage, the history and the leathery resignation that Eastwood does here. Eastwood plays Bill Munny as though the weight of every life he took on screen, from The Man With No Name to Dirty Harry, is bearing down on him. And of course he’s ably assisted by a killer supporting cast, particularly Gene Hackman, Morgan Freeman and Richard Harris, and a magnificent, epic but intimate script from David Webb Peoples (“Blade Runner“). Eastwood has never felt so confident, so fluid and expressive behind the camera either, and his take on the genre sets a high watermark that few if any westerns have lived up to since. Brooding, broken and brave where more often recently Eastwood has seemed a little risk averse, the success of this defining Western can be thanked for revitalizing a genre that had been in danger of waning from our screens. And what better director could there possibly be for that?
Agree? Disagree? You can comment below. Go ahead. Make our day.
— Kevin Jagernauth, Drew Taylor, Oli Lyttelton, Katie Walsh, Sam C. Mac, Jessica Kiang, Mark Zhuravsky, Rodrigo Perez
