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Clint Eastwood’s back in his cowboy hat at 91 — but is Cry Macho his last film?

Kevin Maher on the mellowing of an icon as Eastwood’s eulogy to his tough-guy past comes to cinemas

Clint Eastwood
Clint Eastwood
GETTY IMAGES
The Times

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On a mild November morning last year, on a film set in New Mexico, something extraordinary happened. Clint Eastwood got up on a horse. The 91-year-old Hollywood icon (and that term, for once, is correctly applied — sorry, Chris Pratt) was directing and starring in his first western since his 1992 Oscar-winner Unforgiven.

The film, Cry Macho, features Eastwood as a washed-up cowboy and former rodeo star, Mike Milo, who is sent on a mission south of the border to retrieve a neglected child, Rafo (Eduardo Minett), from his evil mobster mother.

Midway through the movie Mike decides to teach Rafo the basics of horsemanship, which requires some equine action of his own. Eastwood claims that he hadn’t been on a horse since shooting Unforgiven and so the riding scene was especially significant. The movie’s producer Tim Moore says: “The first day that we filmed the scene of him up on that horse the crew was so excited. It was a very special moment. It’s Clint! Back up in the saddle again!”

With Eduardo Minett in Cry Macho
With Eduardo Minett in Cry Macho
ALAMY

Eastwood, of course, knows about special moments and how to milk them. Everything has significance in his cinematic universe. The lines become artworks. “Go ahead, make my day!” “Dyin’ ain’t much of a living, boy.” “I’ve killed just about everything that walks or crawls at one time or another, and I’m here to kill you, Little Bill.”

The characters become self-referential evolutions. Harry Callahan (from Dirty Harry) begat Frank Horrigan (In the Line of Fire) begat Walt Kowalski (Gran Torino). And the performance style (squinting eyes, teeth gritted) remains fixed in stone. Eastwood’s western director Sergio Leone once joked that Clint had just two expressions — “With hat, and no hat.”

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Cry Macho, thus, begins with the most special moment of all. It’s the long-awaited return of Eastwood in cowboy persona (with hat). Initially he is only glimpsed in several tiny teasing half-shots. He’s driving a battered pick-up truck across a desert road, so we see those squinting eyes in a rear view mirror, then the back of the cowboy hat, and a cutaway to the brown leather cowboy boots.

Remember, this is Eastwood directing Eastwood, stirring the audience into a frenzy at the thought of revisiting the virile heroics of the Man with No Name (from A Fistful of Dollars), who begat Josey Wales (The Outlaw Josey Wales), who begat Will Munny (Unforgiven). And then, eventually, the car stops, Eastwood gets out, and we are permitted to finally, fully, see him. And, well, he’s really old.

The jeans are baggy around the near comically high waist, the cowboy shirt hangs loose on the torso, the hair is white, thin and wispy, and the frame slightly stooped. And the film that follows knows this and puts Eastwood into painful situations, first against bad guys, where all he can do is hide, and then against sexy vamps, where all he can do is tremble and exit nervously (“I think I’d better get the hell out of here!”). He’s even given a younger Mexican paramour, the raven-haired Marta (52-year-old Natalia Traven), with whom he seems oddly impotent, at best avuncular.

Near the end of the movie the young Rafo senses, as we do, that Milo, and Clint, is finally past his prime and upbraids him with: “You used to be tough, but now you are weak! You used to be strong, macho! But now you are nothing!”

Milo snaps back sadly: “I used to be a lot of things that I’m not now.” It’s a killer line, one that sends a righteous jolt of regret back through the Eastwood canon. But we’ve barely had time to process its significance when, upending his entire tough-guy catalogue, he says with a sigh: “And I’ll tell you something else. This macho thing is overrated.”

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And there it is. The Eastwood movie motif writ large — the unexpected. He has always done this, but few have bothered to notice. He has consistently turned away from the familiar and the formulaic to make wild-card dramas such as The Beguiled, Bird, The Bridges of Madison County and Letters from Iwo Jima when the world simply wanted more Harry.

Clint directs and stars in Cry Macho
Clint directs and stars in Cry Macho
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Better still, his unexpected movies often contained within them a deliberate critique of the mainstream star he had become elsewhere. This macho thing, they often said, was overrated.

When I interviewed him last, for the Angelina Jolie child abduction drama Changeling, Eastwood admitted that, after that film and Million Dollar Baby, he was increasingly drawn to women’s stories. He didn’t like it, he said, when women on screen were “relegated to either romantic roles or fluff pieces. So the appeal, for me, is to make a picture about a real woman.”

This from Dirty Harry? We were speaking over the phone, him from his home in Carmel, California, where he was briefly mayor, and me from north London. My three-year-old daughter had croup at the time and, home alone, I cradled her for the duration. Eastwood, on hearing her bark, immediately melted (“The poor little thing,” he kept repeating, every time) and eventually began to reflect on his often haphazard parenting, and the tendrils that trailed back to his unhappy childhood.

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“I just didn’t have the knowledge of my older children, the way I do now of my younger children,” he said as the father of eight, and someone who arrived at the rewards of parenthood at the 11th hour. “But every person has high points and low points in that department. And now everybody’s grown up and, well, what do you do?”

Eastwood in September at his home in California
Eastwood in September at his home in California
GETTY IMAGES

He then spoke about his childhood, in Depression-era California, following his peripatetic father (sometimes a steel worker, then a petrol station attendant) around the state, starting in different schools every year and becoming essentially friendless. “You eventually learn to exist by yourself, to play by yourself and to get along by yourself,” he said.

His mother, Margaret, once said that he made up imaginary friends for company, and this is what led him to become an actor. There is definitely sadness at the root of his craft, but also, perhaps like his father, a certain restlessness.

After finishing school, Eastwood did two years in the army (he was drafted) as a swimming instructor, then apprenticed on the TV show Rawhide before landing his big break with A Fistful of Dollars.

There were multiple relationships, resulting in a messy, highly publicised split in 1989 with the actress Sondra Locke, who then detailed her tempestuous years with Eastwood in the tell-all biography The Good, the Bad, and the Very Ugly.

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Politically he seemed to be a conservative Republican, beloved of Ronald Reagan, and he did indeed make a shambolic appearance at the 2012 Republican National Convention, famously addressing an empty chair as if it contained the invisible presence of Barack Obama (don’t ask).

However, he also rejected the Republican Party and was an opponent of the Iraq War. The politics in his movies too are mercurial and difficult to pinpoint, balancing every racist, neo-fascist enforcer (enter Harry Callahan) with a kind-hearted do-gooder (Bronco Billy), a peacenik war drama (Flags of Our Fathers) or a ringing endorsement of euthanasia (Million Dollar Baby).

A lot of observers call him an “enigma”. Martin Scorsese calls him the “link” between old and new Hollywood, saying recently: “I think maybe that Clint is the last vestiges of the golden age of the Hollywood studio film. There’s no doubt that he’s the link from the cinema that I grew up with, and loved, to the modern day.”

Eastwood’s one consistent creative stance, however, as well as his penchant for restless experimentation, has been his refusal to contemplate retirement. When I spoke to him he found the idea abhorrent and suggested that longevity was connected to a crammed professional schedule, saying: “I won’t be retiring unless someone thinks I should retire.”

These days, though, he seems to have mellowed somewhat and has even openly admitted: “I don’t have anything else percolating at the moment.” This raises the prospect that Cry Macho, the film about the hollow triumph of screen heroism, might actually be his last, and a tremulous sad-faced sign-off to a lifelong tough guy. Now that would be unexpected. Which is typical Clint.
Cry Macho is released on November 12