Why this might not seem so easy

How do you even begin to define the prolific, six-decade (and counting) career of Clint Eastwood? To some, he’s one of the greatest living American filmmakers, at 91-years-old still turning out complex interrogations of genre, history and the myths of the national unconscious. To others, his success – and critical estimation, a long time in the making – remains an enduring mystery. To film critic Pauline Kael, he was a “cold cod”, while Norman Mailer called him “not just a fabulous success at the box office, but important.” 

To audiences, he’s the laconic, pop-cultural icon, born the moment he asked four mangy killers to apologise to his mule in A Fistful of Dollars (1964). He’s won two Oscars for directing two best picture winners (Unforgiven, 1992; Million Dollar Baby, 2004), rare events in which critics and the general public approached some kind of detente on what a good Eastwood picture looks like. Many of the films that critics deem among his best made little money, while audiences swarmed to his bare-knuckle banter with an orangutan sidekick… twice.

For some people, he was the mayor of Carmel, California (campaign slogan: “Go ahead, make me mayor”); for others, the guy who rambled to an empty chair at the 2012 Republican National Convention. Attempts to map Clint’s personal politics on to his films have proven a popular critical parlour game since his earliest days as director and star. Suffice to say that at one time or another, he’s sent both the right and left into pearl-clutching conniptions.

Rawhide (1959-65)

There’s never been a director-producer-star (and sometime composer) to achieve his level of success in American cinema. Following a long-running stint on the TV western series Rawhide (1959-65), Eastwood made his name in the ‘Dollars’ trilogy, a trio of big-screen Italian oaters by director Sergio Leone. In 1971 he directed his first film with Play Misty for Me; the same year he introduced the world to Inspector Harry Callahan in Dirty Harry. Clint had quickly become a superstar synonymous with screen violence, casting the archetype of the renegade cop and the western antihero in stone. 

What followed was a directorial career that served as a reckoning with his own screen persona – one that sought to complicate and dismantle the very mythologies he’d helped create.

The best place to start – Dirty Harry

“Fascist medievalism” was how Pauline Kael described Dirty Harry, “a right-wing fantasy… a single-minded attack on liberal values.”

The film was a box office smash, the fourth highest-grossing of 1971, and finds Clint at his movie star peak. It was directed by Don Siegel, a filmmaker whose no-nonsense, economic efficiency would have a lasting influence on Eastwood’s own career as a director.

Dirty Harry (1971)

Dirty Harry effectively transposes the heavily symbolic, mythic rituals of the west on to the contemporary streets of San Francisco, pitting Clint’s vigilante cop against a sadistic serial killer known as Scorpio. Eastwood’s Callahan is a lib-baiting desecration of the heroic archetype, at once an officer of the law and a law-breaking outsider, one who takes matters into his own hands when the rulebook proves inadequate to the task. 

For all the muscularity of its direction – and its operatic ironies of tone – debate raged on the film’s ideological quandaries. While Siegel and Eastwood had a hit on their hands (“and their conscience,” said one critic), the film had clearly touched a nerve, leading to protests come Oscar night.

Magnum Force, the first of four sequels, appeared in 1973. Written by John Milius and Michael Cimino (from a treatment by none other than Terrence Malick), the film was something of an apologia for the first Callahan flick. As mea culpas go, it’s far from convincing, and much less interesting than Eastwood’s own, self-aware spin on his iconic character in Sudden Impact (1983).

Wherever you land on the series’ moral complexities, it remains a key entry point ahead of the genre cross-examinations that would follow.

What to watch next

High Plains Drifter (1973)

Cheers erupted on the set of Cry Macho (2021) when a nonagenarian Eastwood mounted a horse on-camera for the first time in three decades. He hadn’t made a western since Unforgiven, but remains indelibly connected to the genre in the popular imagination.

“That wasn’t what the west was all about,” said John Wayne after seeing High Plains Drifter (1973). “That isn’t the American people who settled this country.” Eastwood’s second feature as director, High Plains Drifter is an apocalyptic subversion of western iconography, a fire-and-brimstone assault on the moral decay of the ‘god-fearing’ townsfolk who hire Clint’s spectral gunslinger. The critic Robin Wood described its relation to My Darling Clementine (1946) as “in striking parallel with the way Night of the Living Dead (1968) relates to Meet Me in St. Louis (1944).” Little wonder Duke was pissed.

Twelve years later, Eastwood sounded echoes of the film in Pale Rider (1985), doubling-down on High Plains Drifter’s supernatural elements for an ecologically conscious riff on cowboy classic Shane (1953). The existential qualities of the two films are brought closer to earth in his 1976 masterpiece The Outlaw Josey Wales, a film that begins in the mytho-poetic register that made Clint a star, before shifting into an incisive allegory of the violence in Vietnam.

A Perfect World (1993)

It’s also a film about community – or rather, making one’s own community – a recurring Eastwood theme from Bronco Billy (1980) to Million Dollar Baby, often in dialogue with notions of inherited cycles of violence and a distrust of institutional structures. It’s all there in two of his finest films, the Kennedy-era road movie A Perfect World (1993) and the harrowing, Boston-set tale of a community riven by trauma, Mystic River (2003).

It’s often said that Eastwood’s ‘mature’ period started with Unforgiven, but it really begins four years earlier with his elliptical Charlie Parker biopic Bird (1988). This was the first in a series of character portraits to interrogate 20th-century history. Changeling (2008), J. Edgar (2011) and Jersey Boys (2014) would follow, but it’s the WWII diptych of Flags of Our Fathers (2006) and Letters from Iwo Jima (2006) – which surveyed the eponymous battle from both American and Japanese perspectives – that proved his greatest critical triumph. The former, especially, stands as a heart-wrenching treatise on the perils of fame, and a searing deliberation on the tension between the legacy of an image and its underlying truths.

Sully (2016)

It may well be pre-emptive to describe the last decade as Eastwood’s late-period, but four films he made between 2014 and 2019 – American Sniper, Sully, The 15:17 to Paris and Richard Jewell – ought to be taken together as a stunningly complex quartet on the question of heroism.

But perhaps three films stand as the most essential, self-reflexive works in the Eastwood canon. White Hunter Black Heart (1990), Unforgiven and The Bridges of Madison County (1995) are the most explicit examples of the filmmaker wrestling with his legacy. These are idiosyncratic masterpieces on questions of violence, masculinity, self-image and the false fronts of American iconography.

Where not to start

Clint had fancied himself as a singer for a while, even going so far as to release a 1962 album called Rawhide’s Clint Eastwood Sings Cowboy Favorites. In 1969 he signed on for an adaptation of a western musical that had proved a huge success on Broadway. You don’t get much change from three hours with Paint Your Wagon (1969), a nightmare of a production that saw songwriter Alan Jay Lerner fight running, budget-doubling battles with screenwriter Paddy Chayefsky. Clint just about holds his own, but no-one really escapes unscathed. Roger Ebert sums it up best in his contemporaneous review: “The film doesn’t inspire a review, it doesn’t even inspire a put-down. It just lies there in my mind – a big, heavy lump.”

Cry Macho is in UK cinemas from 12 November 2021.

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