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In a singular career, Clint Eastwood has established himself as America's rare genuine conversation artist

Clint Eastwood, seen on the set of Flags of Our Fathers in 2006.

Clint Eastwood has weathered typecasting, box-office bombs, palimony lawsuits, sundry torrid affairs, a skin-cancer scare and two critically reviled movies that saw him starring opposite a trained orangutan. But it was the 2012 Republican National Convention that almost proved his undoing.

On Aug. 30, 2012, Eastwood took the stage at the Tampa Bay Times Forum to chants of "Make! My! Day!" and ecstatic applause. "I know what you're thinking," Eastwood growled. "What's a movie tradesman doing out here? They're all left-wingers out there. Left of Lenin!" His thinning grey hair combed back, looking vaguely emaciated and skeletal inside an oversized suit jacket, Eastwood proceeded to address an empty chair, meant to represent then-president Barack Obama.

Roger Ebert called the appearance "sad and pathetic." Wisconsin's Republican governor Scott Walker admitted to cringing. In Texas, a racist hanged an empty chair in effigy. Eastwood's RNC appearance left an indelible, unfortunate mark: the aging icon as cantankerous old coot. To riff on the timeless wisdom of Catherine the Great: In Hollywood, one can enjoy a long, prosperous career, abounding in compelling creative gambits. But talk to one chair and you're a chair-talker for all eternity.

Yet, despite Clint Eastwood's shilling for the ill-fated Romney/Ryan ticket, and the accusations of racism and jingoism that have dogged the writer/director/composer/star's recent films, his politics feel trickier to parse. Eastwood's filmography reveals curious political complexities, which bear examining as he girds himself against the imminent calls of racism, war-mongering, conservatism etc. likely to be levelled at his latest film, biographical thriller The 15:17 to Paris (opening Feb. 9), about a trio of Americans thwarting a terrorist attack on a high-speed European train in 2015.

On paper, Eastwood's a registered Libertarian. On points, he falls to the left of the political spectrum – having expressed anti-war, pro-gay-marriage, pro-choice, pro-gun-control, atheist sentiments. Eastwood's artistic imprimatur varyingly betrays and belies his more cringe-worthy public comments.

In a 1984 review of the Eastwood-directed, Eastwood-starring thriller Sudden Impact, critic Dave Kehr wrote: "Clint Eastwood is hardly ever discussed as a serious filmmaker, but when he is, it's as a political filmmaker – a manufacturer of right-wing tracts in favour of harsh Nixonian notions of law and order." Well before the RNC "Chairgate," Eastwood's star persona had been defined by a flinty and somewhat retrograde hardness.

The abiding historical and critical take is that much of Eastwood's output as a director, particularly since his Oscar-winning 1992 western Unforgiven, has worked to soften this image. There was 1995's Bridges of Madison County, a genuinely affecting romance in which Eastwood played a roving, workmanlike photojournalist resigned to the fact that he'd never be a proper artiste (a fine auteur statement for Eastwood's lean, precise, low-key-masterful "movie tradesman" status). Later, Million Dollar Baby bared the heart beating behind the scowling, tough-guy artifice and petrified-wood visage.

Unforgiven itself has been variously hailed as "subversive," "revisionist," "morally complex" and "genre-reinventing." It's regarded as a film that upended Eastwood's persona as lonesome western hero, and the very western genre itself. (Let's bracket the fact that the genre was upended at least as far back as Sam Peckinpah's The Wild Bunch in 1969, if not circa George Stevens's 1953 epic Shane, a film which provided a template for Eastwood's earlier revisionist star vehicle, 1985's Pale Rider.)

Reading back through such appraisals, the temptation is to reprint the legend – much like Unforgiven's squirrelly wild-west biographer, W.W. Beauchamp (Saul Rubinek).

There's no doubt that Unforgiven is a consummate piece of American filmmaking, which subverts countless tropes of western cinema. The lone gunman (Eastwood's Will Munny) is a callous murderer; the sheriff (Gene Hackman's "Little" Bill Daggett) is a cowardly sadist; (almost) every act of violence is met with consequence. Yet Eastwood revises these tropes only to reassert the most essential myth of the western: the lone hero, cast against a backdrop of senselessness, rising with dignity from the mucky moral morass.

Between Munny's third-act turn into selflessness, in which he guns down a saloon to avenge his partner (Morgan Freeman), and the closing title card's suggestion that the murderous Munny always nurtured this faintly flickering moral light (despite a life of getting drunk and murdering innocents), Unforgiven's revisionary bleakness works to cast its antihero's redemption further in relief.

Eastwood's career revisionism follows a similar tack. In Gran Torino, he plays a retired Korean War vet who strikes up an unlikely association with his Asian-American neighbours. The film earned a certain ironic cachet for its wall-to-wall ethnic slurs (collected across several YouTube compilations), for the arch-grumpiness of Eastwood's character (who literally growls "Get off my lawn" more than once), and for its closing, Eastwood-sung theme song about a car. If Unforgiven tweaked Eastwood's gunslinger image, Torino plays like a Dirty Harry Elseworlds adventure, a return to what New York Magazine's David Edelstein called the "Cro-Magnon right-wing vigilante racist" persona.

Gran Torino unfolds like a lengthy Andy Rooney soliloquy against the regime of political correctness. It envisions a world where joking about racial difference somehow works to alleviate, instead of exacerbate, that difference. Its ideal is that of the local barbershop, where customers converse in a shared language of stock Polish, Irish and Italian clichés. What Grand Torino never considers is that the cheery exchange of ethnic slurs between white men of European stock is not the same as an exchange between those white men and members of minority Asian communities.

In Gran Torino, Eastwood played a retired Korean War vet who strikes up an unlikely association with his Asian-American neighbours.

American Sniper, Eastwood's 2014 biopic of Navy SEAL sharpshooter Chris Kyle, was an ideological flashpoint. The real-life Kyle, who was murdered by a fellow veteran in 2013, was self-mythologizing and ruthless, describing Iraqi citizens as "savages," and worse, in his autobiography. Eastwood's Kyle is poignantly embodied by a career-best Bradley Cooper as a coil of conflict and twitchy PTSD. Eastwood reworks the jingoism of the historical Kyle as a kind of rough-hewn humanism. He's less a proponent of the United States' militaristic culture than a victim of it. Eastwood complicates the dichotomous Us versus Them world view of Kyle (and George W. Bush, and the American public that rendered them heroes) in subtler shades of grey.

One gets the nagging sense that Eastwood's humanism isn't so much countenancing an inherent regressivism as covering for it. American Sniper may well be a Rorschach movie: neutral enough to play to hawks and doves. But isn't such neutrality itself a form of ideological manoeuvring? The "support the troops, not the war" stance of Sniper is not so much complex as disingenuous, even incoherent: like a vegetarian who hates eating meat but wholeheartedly endorses factory-farming. Eastwood's humanism reveals itself as politicized libertarianism, in which characters (Hilary Swank in Million Dollar Baby, Tom Hanks's put-upon commercial flyboy in Sully, Eastwood's various redemptive avatars in Unforgiven, Absolute Power, True Crime and Gran Torino) reassert their individualism in the face of unfeeling governing systems, and the grander architecture of a wholly capricious moral universe.

In crasser, more ideologically minded terms, understanding Eastwood's conservative-libertarian auteur bent provides a genuine insight into the American psyche. As Rolling Stone's Matt Taibbi wrote in a (too) dismissive attack on American Sniper, "The only thing that forces us to take it seriously is the extraordinary fact that an almost exactly similar world view consumed the walnut-sized mind of the president who got us into the war in question."

American Sniper, Eastwood’s 2014 biopic of Navy SEAL sharpshooter Chris Kyle (played by Bradley Cooper), was an ideological flashpoint – even as the film proved to be notably politically neutral.

Certainly, Eastwood's movies provide a vantage on a certain conservative attitude in American life, one that privileges the liberty and dignity of the individual above all else. They're more about riding fences, less about sitting on them.

What situates Eastwood among the pantheon of conservative American film artists (including old-school classicists such as John Ford and Howard Hawks) and likewise distinguishes him from the more reactionary strain of contemporary hacks (Michael Bay, Zack Snyder etc.), is that he comes by his politics honestly. And understanding the political dimension of Eastwood's art does not diminish that art, but enliven it.

Art, after all, is not the revelation of some deep truth, but the expression of that truth. And Eastwood expresses his truth with intellect, genuine sympathy and an impressive economy. He has an eye for character, a canny way of exploring the changing nature of the American identity and a genuinely masterful way of entwining plot lines to manage tension ( Sudden Impact, Unforgiven, True Crime, Mystic River). Even the structuring conceit of his latest film – casting non-actors as themselves – reveals a rare gameness of spirit, a desire to challenge himself so late in his career.

At 87, the sun may well be setting on Eastwood's career, his art and his political life. Perhaps there's no place for such a hardened, iconoclastic, near-mythic figure in America's increasingly ideologically bifurcated political landscape. Even for those who may rebuff, or resent, the seriousness of Eastwood's politics, it becomes difficult not to wax a bit nostalgic, particularly in the face of the contemporary conservative-right's ferociousness and slobbering idiocy.

And so there's comfort to be found, perhaps, in the wistful, clumsy poetry of Robert Kincaid, Eastwood's aspiring-artist avatar in Bridges of Madison County: "The old dreams were good dreams; they didn't work out, but I'm glad I had them."