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Feeling Lucky at 90: The Clint Eastwood Passion Project

One of Hollywood’s most enduring icons enters his 10th decade on the planet this week. After more than 50 films, 38 directed by the man himself, what’s left to say about Clint Eastwood? Two fans look at old favorites and a few less heralded works to paint a picture of sustained, often unpredictable artistry.

Ringer illustration

Adam Nayman: Hi, Sean! We’ve decided to go back and forth on Clint Eastwood in honor of his 90th birthday, and so I thought it would be good to start with a question: Does the guy belong on some hypothetical Mount Rushmore of Hollywood cinema? But then I realized that I was asking the wrong question. The real talking point is whether it’d just be better—and more efficient—to carve an entire monument in his image.

Even the most ambivalent among us would agree that there are at least four iconic, public-facing Clints: the poncho-wearing outlaw; the Magnum-flashing bad lieutenant; the gravel-voiced romantic; and the grumpy old man defending his lawn. (Honorable [?] mentions to the monkey-loving truck driver and the conservative performance artist.) And if we’re talking about Clint the director—the internationally acclaimed artist with two Oscars and a lifetime Palme d’Or from Cannes—then the portrait gallery expands exponentially. How many filmmakers have stayed so prolific and unpredictable over six decades? Even if Eastwood’s output is closer in spirit (if not style and tone) to Woody Allen than Steven Spielberg—a writer-director-star who honors bygone genres and masters as well as his own personal, obsessive fetishes—he sometimes displays a sense of scale and commercial savvy to rival the latter. Seriously: It’s one of the great paradoxes how a guy with such a seemingly minimal arsenal as a movie star ultimately contains multitudes. The exterior is granite. Inside resides nothing less than a 20th-century museum of American history, culture, and politics whose most recent exhibits—including the interconnected quartet of American Sniper, Sully, The 15:17 to Paris, and Richard Jewell—are expressly millennial.

An addendum to the above: I don’t particularly like Clint Eastwood. I definitely don’t love him the way that a lot of my friends and peers do, and I’ve been told that this has to do with being Canadian and, as a result, being cut off from the source of that essential, monumental Clint-ness: “There was no one more American than he,” opined Norman Mailer, who knows from problematic icons, being one himself. I think it’s more to do with a wariness of and distrust toward the ideological content of his movies, a distinct rightward tilt whose owner comes by it honestly and, to his credit, expresses it less monolithically than one might expect. It was, for instance, interesting circa 2004 to see a guy long vilified by liberal commentators for Neanderthal politics getting pilloried by the right for essentially advocating for euthanasia in Million Dollar Baby—a movie whose shameless emotionalism proved difficult for even skeptics to resist. We’re all guilty of going into certain movies with our hopes low and our guard up, and I fully admit to feeling surprised when a late Eastwood movie lands the equivalent of a sucker punch: Million Dollar Baby knocked me flat, and more recently, the beguiling weirdness of The 15:17 to Paris, with its real-life heroes playing versions of themselves in what mostly amounted to a meticulous re-creation of a banally bromantic summer vacation, broke my defenses completely. What a strange, risky, borderline-unhinged movie, I thought on my way home from the theater. Seriously… who does this?

I guess what I’m saying is: Not everybody’s Clint Eastwoods are created equal, and I’m wondering if between the two of us we could craft a narrative that runs the Gauntlet (see what I did there) of his nearly 60-year career without just rehashing the classics. I think, for instance, that we’d both agree that Unforgiven is pretty good. I know you’ve picked some titles and so have I—want to get us going by reaching back to his early days as an action star?

Sean Fennessey: Sure. I share a similarly distanced but obsessive admiration for Clint: gobsmacked by the breadth, length, and incredible weirdness of his career. His movies feel like they were pre-programmed into my viewing history, but that underestimates just how many and motley they are. The iconography tends to overwhelm the eccentricity and variety of his work, especially in the 21st century. But it took him many years to grow into that cult of personality. If the Sergio Leone trilogy and the early post-Rawhide Westerns like Hang ’Em High and Coogan’s Bluff set a template for Eastwood’s acting style and minimalist characterization, his early war movies—which are closer to man-on-a-mission adventure tales than trench-bound battle pictures—saw him challenge Steve McQueen and Sean Connery for “look cool and take care of business” swagger. The first of these, and still my favorite, is 1968’s Where Eagles Dare, Brian Hutton’s Wolfenstein 3D–esque story of the Allied infiltration of a Nazi castle, where Eastwood and a debonair Richard Burton cross and then double-cross the German high command.

Where Eagles Dare (1968)

Eastwood doesn’t do much in the movie other than look imposing, furrow that Mount Rushmore–worthy brow at Burton, grumble about British Intelligence, and blow shit up. But what blown-up shit! Fans of Inglourious Basterds can see traces of the talky tavern showdowns that preface noisy shootouts dotted throughout Eagles, while Inception stans will see the very same visceral yet elegant physical style of filmmaking that Christopher Nolan deploys in the snowbound third act of his mind-bending thriller. And if you like Tom Cruise’s Mission: Impossible series, well, Eagles is one of the earliest high-wire-stunt masterworks, including among its many set pieces an aerial cable car sequence that is both breathtaking in its storytelling and mystifying in its execution. Hutton, who would go on to work with Clint again in 1970s World War II caper Kelly’s Heroes, started his career around the same time as his star, appearing as an actor in ’50s Westerns before transitioning to impressive, if slightly undistinguished, work behind the camera. You can tell what Clint gleaned from him: flinty, unfussy pacing and a grand sense of action. Where Eagles Dare, the best movie Rick Dalton never made, is just a precursor to Eastwood’s extraordinary 1970s, in which he starred in 16 films, mostly hits, and began directing his own movies, too, helming six. Though it strays from his Western antihero persona, it shares obvious touch points: the foreigner from the West dropped into dangerous circumstances and left to fend for himself with his wiles and his Winchester. It wouldn’t be the last. About those directing gigs, though, Adam...

Adam: I can’t pretend total objectivity about Play Misty for Me, since I was told from an early age that it’s the only movie ever made where the romantic leads have the same first names as my parents. Whether that made me like it more or less when I saw it as a teenager, I can’t say, but it’s definitely the sort of trivial detail that’ll stay lodged in my brain long after I’ve forgotten the plot points of better or more important works of cinematic art. Clint’s David Garver is a West Coast DJ whose seductively laid-back on-air persona extends to his personal life: He’s a lady killer whose latest one-night stand—a longtime listener named Evelyn (Jessica Walter)—turns out, after a short courtship, to literally have homicidal tendencies. The title refers to Evelyn’s near-nightly telephone requests for Erroll Garner’s jazz standard “Misty,” but by the time she’s quoting Edgar Allan Poe’s poetry, it’s clear that she’s got more Gothic tastes—and also that if she can’t have David, nobody else will.

The pioneering aspect of Play Misty for Me as a proto-slasher movie is well documented: It’s hardly the first movie with a femme fatale, but elements of its plot and imagery directly anticipate Fatal Attraction, including the bit where Evelyn slashes her wrists in a cracked bid for sympathy as well as the knife-wielding climax. As a star vehicle for Eastwood coming out the other end of his early Westerns and war movies, it’s shrewdly designed, casting him as a contemporary, urban culture vulture—a relaxed jazz aficionado rather than a man of action. But as a directorial debut, it’s downright fascinating, as Eastwood’s long-simmering bid to adopt artistic control over his career after a decade and a half of taking orders on film sets manifests in a story of a man at the mercy of a murderous woman—a near-helpless object of desire without recourse to adequately defend himself at the onset of the feminist ’70s.

Any discussion of an implicit or active misogyny in Eastwood’s body of work has to take Play Misty for Me as the primal scene, especially since Clint was the one calling the shots; the scene where Evelyn angrily slashes a photo of David’s face layers scorned-lover clichés on top of some genuinely startling and self-aware toying with Eastwood’s image. As in The Beguiled, which also came out in 1971, the subtext is that Clint’s sexual charisma is enough to drive a woman insane (or give her the final push along the way). It’s astonishing to see Walter, now established as an expert and veteran comedienne via Arrested Development and Archer, throw herself into such an earnestly clichéd role, working up enough obsessive momentum in her acting to offset her director-costar’s affectless passivity. That the gender politics of Play Misty for Me have aged badly is no surprise—they were retrograde upon release. But considering how many subsequent Eastwood movies would offer up pro forma love interests, the film’s portrait of a relationship in formation, dissolution, and, finally, all-out chaos is comparatively compelling—and would make an amazing double bill with 1983’s Sudden Impact, featuring Sondra Locke in a more sympathetically psychotic role. But I’m getting ahead of things—we can’t talk about a character dubbed by critics as “Dirty Harriet” without checking in with Dirty Harry…

Sean: Well, yes, about Harry Callahan: He’s the most important figure in action movie history, an avatar of crime-and-punishment American fascism, and the star of a damned brilliant movie. Important enough for ya, punk? Dirty Harry is the third film collaboration between Eastwood and director Don Siegel and the first of two in 1971. Siegel and Eastwood would go on to make five movies in all, including 1979’s Spartan, Bresson-influenced Escape from Alcatraz, but Dirty Harry is the one on which Clint’s legend was truly made. Sergio Leone molded him into the commanding screen icon of his time, and Eastwood’s own directorial efforts burnished his vision of an American masculinity waxing and waning between power and repose. But it was Siegel’s wryly funny and yet angry portraits of the actor that persevere—the curled lip, the starchy tweed suit in the San Francisco sun, the .44 Magnum gripped tightly like a sword—that are likely to lead his obituary ... if that day ever comes. At 90, Clint still seems indestructible; last year, news stories about his refusal to abandon his office while completing the edit of Richard Jewell after a fire struck at the Warner Bros. lot read like a parody of his Gran Torino, Greatest Generation, alpha male energy.

Dirty Harry (1971)
Warner Bros.

What lingers for me about Dirty Harry is not the evident anxiety of a rageful peace officer coping with inexplicable evil—in this case, a Zodiac-esque killer played with delirious glee by Andy Robinson. It’s Eastwood’s flair for the imperious colliding with Siegel’s precise yet hyperdramatic staging that I can’t shake. Take the infamous football field sequence.

In less than two minutes, you have Peeping Tom–ish first-person handheld perspective, those staccato cuts as the lights hit the football field, Lalo Schifrin’s tittering score, the exaggerated perspective on Harry’s Magnum firing at the perp, a close-up on Robinson’s shrieking face, and that final tailing helicopter shot pulling far away from the field, which has been ripped off thousands of times. Right before that moment, Harry looms large over the criminal, a simple representation of Dirty Harry’s answer to the question of how to defeat evil: without restriction or control, at any cost. Harry Callahan—leaping from bridges onto buses, firing at criminals from a great distance, sparring with evil and bureaucracy—is the personification of an ugly American, but also an avenging angel. Dirty Harry is brutally, philosophically unwoke—call him a relic, a warning, an iconoclast, a monster, a hero. Won’t matter much to him, which is the point—thrashing contradiction masquerading as objective truth. It’s the subtext in Clint’s life and his persona on-screen: Justice may have a toll, but that toll is rarely more important than justice itself. But if we compare him to the other character he created with Siegel in 1971, maybe we can see an alternate history of Eastwood. A guy with a less defensible vulgarity.

After the failure of The Beguiled, the actor reflected on his own screen persona: “Dustin Hoffman and Al Pacino play losers very well. But my audience like to be in there vicariously with a winner. That isn’t always popular with critics. My characters have sensitivity and vulnerabilities, but they’re still winners. I don’t pretend to understand losers. When I read a script about a loser, I think of people in life who are losers, and they seem to want it that way. It’s a compulsive philosophy with them. Winners tell themselves I’m as bright as the next person. I can do it. Nothing can stop me.”

What a perverse and accurate assessment of the movie star landscape of the 1970s. Winners and losers. (Get this guy a blog!) Even Warren Beatty and Paul Newman found ways to destabilize their implacable matinee idol charm. Eastwood, as a wounded Union soldier taken in and cared for by a repressed Southern woman and her young pupils in an all-girls school, also made a bid to complicate his winner’s identity. It didn’t quite work, despite the effort. Corporal John McBurney is not a noble man—he spends half the film trying to fuck a bunch of teenage girls—but he isn’t demonized, exactly; more like emasculated. Eastwood himself said he never saw McBurney as a “bad guy”—more like a participant in a “mutual manipulation society.”

Siegel’s take on the Thomas P. Cullinan novel A Painted Devil is one of the few bombs in Eastwood’s career, but it’s also the movie that led to him becoming an object of affection among Parisian cineastes. The Beguiled is considered a masterpiece in Europe. When Sofia Coppola remade it in 2017, she shifted the perspective from McBurney to the women occupying the home, weaving a feminist ripple into a story that was previously understood as retrograde in its gender politics. Eastwood’s characters are frequently adored by younger, eager members of the opposite sex—a quality that is both disturbing out of context and not terribly strange inside the experience of his movies. But the very destruction of McBurney—who is first seen felled by battle wounds, then thrown down a flight of stairs before ultimately falling prey to his caretakers—is the point of the film. He’s weak, a chump, a hunter with a bum weapon. Tarantino called The Beguiled Don Siegel’s “art film,” and he’s on to something—this movie has impressionistic flourishes, ghostly traces of soul torture, existential despair, and that ceaseless sense of repression. It isn’t Michelangelo Antonioni, but it isn’t that far off. At the heart of it is a loser. I wonder what would have happened if The Beguiled had become more than a fetish object for Cahiers du cinéma. What do you think, Adam?

Adam: I wrote about The Beguiled for this very website a few years back, and I’d say that not only is QT right about it being an art film, but its artiness—which, as engineered by an old-hand director entering his fourth decade on the job, is at once slightly strained and thrillingly, defiantly purposeful—meant that it should have been a hit in the early ’70s, when being close to Antonioni was a going concern for some Hollywood personnel. Think of the flashy modernist flourishes that Alan J. Pakula draped all over Klute—itself a kissing cousin to Dirty Harry, right down to being named for its unconventional detective hero—or the anxious alienation effects in The Conversation, a movie that even a guy who claimed to not understand losers would have probably agreed made beta-male melancholy gripping and compelling. I don’t know if a better box office return for The Beguiled reroutes Eastwood’s career that thoroughly—i.e., actually acting for Antonioni in The Passenger in lieu of Jack Nicholson—but the narrative of Clint realizing that it’s a decade for losers and he’s pulling out of it to win does set up some of the larger-than-life leading roles that he would take on in subsequent years, or else craft for himself as a director-star.

Maybe one of the reasons that I’m so fond of 1980’s Bronco Billy—a mild commercial nonstarter whose popularity paled in comparison to that of the rambling, affable, fundamentally dumb star vehicles Every Which Way but Loose and Any Which Way You Can—is that its title character is actually a bit of a loser, the proprietor of a struggling Wild West Show whose performers suspect that the venture’s days are numbered. In the film’s opening sequence, Billy, who serves as the show’s master of ceremonies in gunslinger drag that knowingly evokes Eastwood’s original screen persona, accidentally wounds a member of the troupe during a knife-throwing act; the implication is that his aim is no longer true. And for all its rollicking, at times borderline-screwball comedy—much of it revolving around Billy’s romance with a flighty heiress in waiting (Sondra Locke) who becomes a kind of bad luck charm—Bronco Billy is very much a movie about a waning potency, both for its protagonist and the genre his lovingly ramshackle entertainment enterprise seeks to inhabit.

The irony of Bronco Billy is that it doesn’t really betray these deeper and more melancholy themes: It’s a crowd-pleasing piece of entertainment, with certain scenes edited as if leaving space for audience applause after Eastwood tells off greedy villains or makes a rousing, show-must-go-on speech to the troops. Which is exactly why, circa 1980—after a run of hits that made him as omnipresent in Hollywood as any other figure of the post–World War II era—it lent itself to fulsome analysis by film critics, by then happy to embrace a can’t-beat-’em-join-’em philosophy.

In a brilliant 1985 New York Times profile of Eastwood, John Vinocur considers what he calls Eastwood’s critical “rehabilitation,” chalking it up not to any sort of profound artistic evolution but rather to a constancy that kept taking on new meanings in a shifting cultural context. What gave Bronco Billy its resonance was a series of extratextual understandings and assumptions about Eastwood—his past success as a Western star; his growing renown as an independently minded filmmaker with a set of close-knit collaborators; his deceptively populist mandate—that split the difference between slapstick farce and self-reflexive portraiture.

“[Bronco Billy] is wildly patriotic,” wrote Vinocur. “The little cowboy home is saved when inmates of a home for the criminally insane sew them a new big top, stitched together from hundreds of American flags.” Eastwood himself backed this reading, explaining, “I wanted to say something about everybody being able to participate. … America is the maddest idea in the world.” It’s telling that in Bronco Billy’s vision, the racially and ethnically mixed members of the show participate by caricaturing their own heritages onstage and by listening to and ultimately vindicating their benevolently self-effacing leader, who gets the girl, saves the company, and concludes with a message of positivity for future generations. Six years before being elected as mayor of Carmel, California, Eastwood was already, in a sense, running for office, leaning into inevitable parallels with his friend Ronald Reagan—except Eastwood was in every way the more charismatic movie star.

Sean: About that charisma: Clint rarely tested himself as an actor, often relying on strength, restraint, and powerful iconography. He’s not really thought of as a thespian—more like a living statue wearing a holster. He’s primarily a physical performer who gives good close-up—the blank stare, the grimace, the rogueish smile. He did challenge himself once though. In 1990’s White Hunter Black Heart, Eastwood took up a new kind of a role—a portrayal of a real-life person, in the thinly veiled form of legendary director John Huston during the making of The African Queen. He directs himself giving a most unusual performance—mannered, transparent, and larded with dialogue. Clint isn’t a naturally garrulous charmer like Huston was in real life, but it’s fun to watch him bend his persona into a new shape. In one particularly memorable scene, he outstrips a not-so-subtly anti-Semitic woman with a long story set during the bombing of London during World War II. It might set the record for most words spoken by Eastwood in a single stretch on screen.

White Hunter Black Heart isn’t exactly a good film—it takes great pains to underline the metaphors of swollen masculinity and its conclusions are overdrawn. Based on screenwriter and author Peter Viertel’s novel that closely mirrors his experience rewriting The African Queen for Huston on location in Uganda, Eastwood’s John Wilson delays the filming of his adventure movie to hunt for an elephant. He quests through the second and third act seeking a great “tusker,” much to the chagrin of Jeff Fahey’s Viertel stand-in, Pete Verrill. The two have a flinty chemistry, not quite father-son—Eastwood was 60 to Fahey’s 37—but something like mentor-mentee. Eastwood might have made a strong Verrill in the ’60s, all internal frustration and external dissolution.

White Hunter Black Heart (1990)
Warner Bros.

The movie is a bridge—charting a course from virility to resignation. A sign of things to come for Clint Eastwood. It ends with the beginning of the shoot, as Wilson softly, hollowly says, “Action.” It’s a self-aware denouement—Eastwood is famous for refusing to use the declarative “Action!” and “Cut!” on his sets, preferring easygoing pronouncements like “OK, let’s go.” (He cites fear of unnerving the horses on his many Westerns for the choice.) His Wilson is defeated at the end of White Hunter Black Heart, beaten by his own hubris. Unlike The African Queen, one of the most beloved Hollywood classics ever made, the film was a total flop—though it competed at the Cannes Film Festival and received mostly solid notices, it slipped into the category of “too arty” Clint projects, along with The Beguiled and his doleful, adulatory portrait of Charlie Parker in 1988’s Bird. I like these movies almost as much as I like the ones that find Eastwood murdering bad guys from a distance. They reveal something about his mind, the way his taste roves more widely than his fame and persona might otherwise lead you to believe. The ’80s were a successful but somewhat anonymous period in his career, lined with sequels and a few unmemorable comedies and noirish thrillers. They’re good entertainment but don’t mean much to his legend. Neither does White Hunter, but my sense is that without it, we wouldn’t get his ’90s to come.

Adam: I’d agree that you can draw a direct line from White Hunter Black Heart to Unforgiven, in terms of Eastwood reckoning with his own legend and legacy: The film’s dedication to “Don and Sergio” suggests a director deeply in debt to his mentors even as its contents unlocked new compartments of artistry. In a way, Unforgiven represents a better version of the bloody gunslinger myth that Eastwood had already spun twice, in 1976 with The Outlaw Josey Wales and in 1985 with Pale Rider—meditations on vengeance with the director-star (type)casting himself as an avenging angel. Unforgiven has more heft than its predecessors because of how it folds the audience’s awareness of Eastwood’s own advancing age—and encroaching mortality—into its relentlessly death-tinged narrative, and the big-category Oscars it earned were fully deserved.

Those statuettes also loomed over the rest of Eastwood’s decade, which presented die-hard auteurists with a mixed bag of literary adaptations from which to suss out their hero’s signature. The best of these was actually made from arguably the worst book. Robert James Waller’s 60-million-copies-sold The Bridges of Madison County was dismissed as a midwestern bodice-ripper, and the inevitable film adaptation was supposed to be directed by Bruce Beresford, the engineer of genteel Oscar fare like Driving Miss Daisy. The story goes that while Eastwood was already set to star as the National Geographic photographer on assignment snapshotting the titular bridges—and along the way falling in love with a bored farmer’s wife (Meryl Streep)—he ended up reading multiple script drafts and getting frustrated as they strayed further from the corny, irresistible source material; he took on the directing job as a way to ensure that a story involving an unusually wholesome, wistful bout of adultery would remain faithful.

Full disclosure: I love The Bridges of Madison County, or at least Eastwood’s version, which draws on the romantic aspects of Play Misty for Me with a couple of big differences. One is that it’s not a case study in girl-phobia that ends with somebody being thrown out a window to their death; the other is that Eastwood proves a generous and even deferential costar to Steep, who gives what is easily her sweetest and most spontaneous seriocomic performance. The potential irony of watching Hollywood’s most acclaimed actress doing her thespian thing—foreign accent, loquacious body language, pregnant pauses—opposite such an ostensibly one-note leading man dissipates in the pair’s perfectly acted (and directed) give-and-take; Eastwood’s gentlemanly reticence and Streep’s mournful, passionate life force are complementary and effectively charged. At its core, The Bridges of Madison County is about the possibility of change within a preordained pattern, and there’s something about the characters’ yearning that brings out Eastwood’s tenderness. Where in the past his on-screen relationships tended to be either perfunctory or weirdly, distractingly personal—e.g., several of the movies he made with Sondra Locke that had ugly professional consequences—in The Bridges of Madison County he managed to renovate and remodel his persona just enough to be lovable. The result is a movie that skirts cliché without fully succumbing to it and whose populist approach belies its degree of difficulty. It’s easy to make a middlebrow paperback into a movie. It’s hard to make it into poetry.

Exhibit B: 1997’s Absolute Power, adapted from a book by professional page-turner David Baldacci, which doesn’t make it halfway to poetry. It’s pulp all the way, with an unmistakable and opportunistic political valence. In the context of the Monica Lewinsky affair and the attendant impeachment proceedings against Bill Clinton, the film’s depiction of a vicious American president (Gene Hackman) presiding over a murderous cover-up—aided and abetted by a shrill chief of staff (Judy Davis) styled as a surrogate for Hillary—couldn’t help but feel loaded. In In the Line of Fire, Eastwood had protected the POTUS from a crazed killer; now the commander in chief was the culprit. Playing a cat burglar who is the only witness to the crime, Eastwood finds an actorly sweet spot: Instead of being caught red-handed at the scene of the crime, his character remagnetizes his moral compass and doles out freelance justice in between attempts at reconnecting with his daughter (Laura Linney). (Note: Estranged or distant daughters are to Eastwood what dead wives are to Christopher Nolan.)

Compared to Unforgiven and The Bridges of Madison County, Absolute Power is a middling movie: The plot is preposterous and the all-star cast—not only Eastwood, Hackman, and Linney, but also Ed Harris, Scott Glenn, and Dennis Haysbert—play their scenes on beat without inspiration. Oddly for a movie about a skilled pro who has a crisis of conscience, there isn’t much conviction in it beyond its wing-nut subtext, and yet it still glides by on the basis of pure, experience-driven craftsmanship, which is of course what Eastwood’s character prides himself on above all. If Unforgiven was about Eastwood trying respectfully to measure up to his masters, Absolute Power showed him keeping his head down and doing his job. It’s an exercise in muscle memory.

Absolute Power (1997)
Columbia Pictures

I can’t work up much enthusiasm for Absolute Power, but there’s still something about its spare, self-contained style and tone that makes me nostalgic. Not for the Eastwood of the ’90s so much as for a modest, Platonic ideal of a ’90s Movie, by which I mean lowish-budget, unironic genre fare unattached to preexisting IP and without franchise opportunities. (If the movie were made today, it’d star Tom Cruise, and he’d be playing Jack Reacher.) Maybe you can tell me why I prefer a throwaway like Absolute Power to the supposedly superior Eastwood Oscar bait that followed in the 2000s—like, for instance, Mystic River, which, underneath all that award-winning acting, is no less of a potboiler than its predecessor. Why was one apparently forgettable and the other canonized on arrival? Do Boston accents automatically confer gravitas? Help me out here.

Sean: You’ve identified another interesting dividing line—pulpy Clintonian simulacra quickly morphs into docudramatic hagiography by way of Oscar prestige. How? I wonder if it had anything to do with Clint’s longtime assistant director Robert Lorenz officially making the transition to producer on Mystic River. And if Mystic River was a portal to renewed respectability a decade after Unforgiven, then Million Dollar Baby was a confirmation of granddaddy status, placing Clint alongside John Ford, Frank Capra, Billy Wilder, David Lean, Elia Kazan, Steven Spielberg, and a handful more filmmakers with two Best Director Oscars and a stranglehold on “visionary” status. For all of its unvarnished emotional manipulation, I still recall Million Dollar Baby as an alarmingly effective movie on first watch. I was pulverized by it. I haven’t returned since; some movies you want to be sentimental about. But the heightened “realness” of Mystic and Million transformed into something unexpected. After putting a spotlight on John Huston 15 years earlier, Eastwood fully absorbs the true-life historical format for the bulk of the 21st century, making nine features about real figures and events, starting with his pair of World War II opuses, Flags of Our Fathers and Letters from Iwo Jima from 2006. I think of this period—2003 through the present—as his airport bookstore phase, riddled with nonfiction page-turners targeting middle-aged men seeking true stories of sacrifice and heroism complicated by systems that hold us back from realizing true freedom.

Iwo Jima, the more distinguished of the World War II dyad, certainly features an interrogation of bureaucracy and power structures to go with its distaste for war. It also pairs neatly with its companion film thanks to a respectful rendering of the battle from the perspective of Japanese soldiers and leadership on the front lines (or tunnels, as it were here). The movie’s austere style and muted palette—all olive and beige shades—shows a kind of restraint. But not completely. At the same time that Lorenz came into the picture, Tom Stern became Eastwood’s full-time cinematographer, blending his washed-out colorways with a rambunctious, roving camera. (There are a helluva lot of dolly shots in this movie!) Iwo Jima is a long way from the rollicking adventures of Where Eagles Dare or the bootstrap jingoism in (the pretty solid) Heartbreak Ridge. It’s a grave, unrelenting portrait of confronting inevitable defeat. And while Flags of Our Fathers reveals some of the stage-managed theatrics of the U.S. military as a rejoinder to its images of bravery and valiance, Iwo Jima shows dignity and fear colliding constantly, and especially during one memorable suicide pact sequence. They’re both amazing films in their own right, but also inseparable. That they were both financial failures in the same year that the oversimplified, abdominally exuberant 300 became one of 2006’s biggest hits is fitting—as movies stood on the brink of superhero mania, Eastwood’s attempts to once again upset the standards of heroism failed to connect. But rather than swoop into the DCEU, it seemed like he self-consciously decided to shift his focus to heroes of a different kind.

Adam: I would agree, but before I go on I have to unpack the implications of “abdominally exuberant,” which is a good way to describe 300 and basically every other Zack Snyder movie: Whatever you think of his films, he’s got a very literal idea of mythmaking, and it involves low-angle shots of ripped dudes glowering into the middle distance. I can’t help thinking that there’s something overcompensatory in Snyder’s cinema, and the same goes for a lot of his early-millennial alpha male brethren—such as Michael Bay, whose hard-on for military hardware is the stuff of legend. American popular culture is awash in thoughtless but potently charged images of heavily armored machismo.

The part of me that wants to see Clint Eastwood as a subversive curveballer looks at a movie like American Sniper, which in parts plays like something directed by Bay—or a straight-faced version of ruthless Bay-centric satire like Team America—and deems it deconstructionist. That part of me suspects that the framing of real-life U.S. serviceman Chris Kyle (a career-best performance by a bulky Bradley Cooper) as an indomitable crackshot is actually a subtle jab at overbearing wartime P.R.—a la Flags of Our Fathers—or reasons that the script’s perspective on the Iraq War is as narrow as a sniper scope because that’s the protagonist’s point of view. The part of me that remains wary of Eastwood’s motivations worries that even as American Sniper psychologizes Kyle as a fragile flesh-and-blood Terminator malfunctioning on the home front, it also uncritically enshrines him as a legend; when Seth Rogen tweeted that the film reminded him of the movie-within-the-movie Nation’s Pride from Inglourious Basterds, he was being funny, but not necessarily stupid.

That American Sniper is still Eastwood’s biggest hit of the 21st century—and, without adjusting for inflation, ever—leaves me doubting the whole subversion thesis, but I don’t discount its embedded complexity, which is of a piece with the movies that came after. In Sully, The 15:17 to Paris, and last year’s Richard Jewell, Eastwood kept returning to real-life stories whose details fit—or could be torqued toward—a worldview in which heroism is at once largely contingent on right-place-right-time circumstance and a laudable expression of professional skill and/or moral superiority. He’s all about guys who come up big in the clutch. Sully stacks the deck by casting America’s most beloved actor as its most beloved commercial airline pilot, and while Tom Hanks is great, I tend to blanch at movies that try to do all of my thinking and feeling for me.

Which is why I prefer—perversely, I’m sure, in your opinion—The 15:17 to Paris, which actually comes closer to Nation’s Pride in the sense that its protagonists literally play themselves, the way that Daniel Bruhl’s (fictional) Nazi sharpshooter did in Basterds. Tarantino and Eastwood are both keenly aware of film history, and there’s precedent for 15:17’s casting coup in the period war films of Audie Murphy, a decorated grunt who re-created his exploits in World War II dramas like 1955’s To Hell and Back. But where QT has made his reputation as a kind of conceptual stuntman, Eastwood—especially the figure we’ve come to know as “Late Eastwood”—is, ostensibly, more of a straight-ahead filmmaker, which is why the film’s collision between classicism and borderline experimentalism is so thrilling for me. I love that Anthony Sadler, Spencer Stone, and Alek Skarlatos—three burly dudes, two with military credentials, who made world headlines in the summer of 2015 by foiling a rifle-wielding assailant on a high-speed train en route to Paris from Amsterdam—are, by any conventional metric, bad actors; I’m fascinated by how that fact bumps up against the undeniable authenticity of having them reenact their own experiences. And I’m absolutely beguiled—like, straight-up gobsmacked—by how that choice results in a film that’s basically a self-consciously bromantic fly-on-the-wall travelogue juxtaposing the sweetly banal banter of some abdominally exuberant dudes with the great landmarks of Europe—like The Trip if Steve Coogan and Rob Brydon couldn’t do impressions and ate cheap gelato instead of expensively subsidized dinners.

Seriously: The 15:17 to Paris is a singular thing, and I can’t stop thinking about all of its fitful contradictions; the continuity between the stilted performance of the child actor playing Sadler and his real-life counterpart; the almost exclusive casting of recognizable TV comedians (Jenna Fischer, Judy Greer, Jaleel Fucking White) as parents and teachers in the early sequences; the Full Metal Jacket poster spied on the wall of a teenage boy’s bedroom; the way the filmmaking drifts along documentary-style before snapping into strapping action-movie mode for the climax; the gelato scene, which is really only 30 seconds long but feels bizarrely epic, as if the question of what flavor the boys are going to choose really, deeply matters.

Mostly, I’m torn between suspecting that the 15:17 to Paris is a gambit that just doesn’t work and the possibility that it’s a neo-Brechtian masterpiece orchestrated by a director who’s demonstrably smarter than his haters. I don’t want Clint Eastwood to make me feel dumb, is my point, and it’s easier for me to see through—or believe that I’m seeing through—the crocodile-tears narcissism of an otherwise entertaining movie like The Mule or the various bad-faith storytelling choices in Richard Jewell than to parse the absolute oddness of what The 15:17 to Paris is or what it does (or doesn’t) represent. It’s a movie that’s practically begging you to make its day by misunderstanding it, and in the end, I’m just outgunned. You win, Clint. And for the record: This punk feels lucky to have no choice but to keep giving you the benefit of the doubt.