Pop Culture

Clint Eastwood is 91 and His Films Just Keep Getting Odder and More Daring

Cry Macho is the latest charming entry in a shockingly adventurous late period. 

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Clint Eastwood in ‘Cry Macho’©Warner Bros / Everett Collection

On January 20, 2019, John Mulaney and Pete Davidson made an appearance on Saturday Night Live’s “Weekend Update” to deliver a report on what Colin Jost described in his intro as “a very important experience.” The set-up suggested Davidson would be talking about his mental health issues and some troubling Instagram posts alluding to suicide he’d made a few weeks before. Instead, the two offered a breathless summary of Clint Eastwood’s The Mule, describing it as “the greatest, weirdest, most bananas movie ever made — about a 90-year-old drug mule.”

It’s a funny bit largely because Mulaney and Davidson don’t have to embellish the details. Directed by and starring Eastwood, The Mule recounts a fact-inspired story in which a down-on-his-luck Illinois horticulturalist becomes the favored means of transportation for a drug cartel, a late-in-life career change that allows him to enjoy the open road and the occasional threesome. You know, one of those movies.

They were not wrong: The Mule is an odd film. But it’s just one entry in what’s been a determinedly unpredictable, sometimes baffling, sometimes thrilling decade for the now 91-year-old Eastwood, that’s found him attempting new genres, trying out new techniques, and charging forward as he piles one movie atop another.

Eastwood has shown no sign of slowing down or offered any talk of retirement. Yet while he seems like one of the healthiest 91-year-olds on the planet, he’s still 91 years old. Each film could be his last, and while other filmmakers might have treated this as a time to coast, Eastwood seems more restless than ever. Even when the films themselves haven’t quite delivered — though a few have delivered spectacularly — they’ve offered reminders that the movie world will be a little duller when Eastwood calls “cut” for the final time.

Eastwood’s most popular roles dominate our perception of his filmography, but he’s challenged himself since his first film as a director, Play Misty for Me, a stalker thriller in which Eastwood’s jazz DJ protagonist ends up looking nearly as bad as his unhinged assailant, played by Jessica Walter. In the years that followed he made westerns and crime thrillers, as expected, but he also made a May/December romance (the little-seen Breezy), a Charlie Parker biopic (Bird), played a thinly veiled version of John Huston (White Hunter Black Heart), and delivered one of his gentlest, and best, performances playing opposite Meryl Streep (The Bridges of Madison County). The closer you look at Eastwood’s filmography, the slipperier it gets.

His unexpected late-career phase kicked off with the 2010 film Hereafter, a supernatural drama scripted by Peter Morgan, a writer best known for history dramas like Frost/Nixon and creating The Crown. The globe-spanning film concerns a handful of characters haunted by visions of the afterlife, including George (Matt Damon), a psychic doing his best to ignore his connection with the Great Beyond. Damon turns in one of his best performances, particularly in a mid-film stretch in which George’s attempted romance with a charming woman named Melanie (Bryce Dallas Howard) reveals the weight of his gift and the distance it’s driven between him and the rest of the world. Hereafter is a worthwhile effort, if a bit shapeless, perhaps due to Eastwood’s habit of filming screenplays as he finds them rather than asking for additional drafts.

Even the recent Eastwood films that appear straightforward from a distance prove to be more complicated upon a closer look. He scored his biggest hit of the decade with American Sniper in 2014, an adaptation of marksman Chris Kyle’s account of service in the Iraq War starring Bradley Cooper. The film works as a stirring story of military heroism but, in its best moments, also as a study of the costs of that heroism. Eastwood’s politics are more complicated than his regrettable talking-to-an-empty chair appearance at the Republican National Convention in 2012. He’s reliably quick to get his back up against liberal ideals but also reliably antiwar, a conflict the film reflects and which helps make it difficult to pin down as either a flag-waving celebration of sacrifice or an elegy for unnecessary bloodshed.

True, there’s a conspicuously fake baby in American Sniper. With late Eastwood, there’s always some clunkiness to get past, but that’s part of the price of admission. He doesn’t fuss over multiple takes when he doesn’t have to. He gets what he needs, then it’s onto the next scene or the next movie. He knows that time isn’t on his side and he has work to get done.

Sometimes that’s a film he really has no business making, like his 2014 adaptation of the long-running Frankie Valli and the Four Seasons jukebox biopic Jersey Boys. The film mostly plays like a take-home version of the show designed to be sold in the lobby after performances, but there’s a fascinating weirdness to Eastwood bringing his flash-free steady-handedness to a big-budget musical. (It’s the film he made after he spent years getting this close to directing A Star Is Born, which would ultimately end up in the hands of American Sniper star Bradley Cooper.)

Other times that means making The 15:17 to Paris, which recounts the true story of three Americans who foiled a terrorist attack aboard a train in 2015. Eastwood cast the real-life heroes, Spencer Stone, Anthony Sadler, and Alex Skarlatos, which sounds like, and is, a bad idea. It’s made even worse by the decision to depict much of Stone, Sadler, and Skarlatos’s trip to Europe before the attack. (It’s nice. They see a lot of famous sites and meet some cool people.) It’s one of Eastwood’s worst films but it’s also one no one else would dare to make. Again, the price of making such big bets is sometimes they don’t pay off.

But sometimes they do. Or mostly do. Were it not for one element, Eastwood’s 2019 drama Richard Jewell would work as an excoriating and stirring depiction of how the police and the media made a pariah out of a hero by rushing to assume the guilt of a security guard who found and reported a bomb at the 1996 Olympics in Atlanta. Eastwood brings a matter-of-fact approach to the storytelling and anchors the film to a terrific performance by Paul Walter Hauser, who’s not afraid to play Jewell as a sometimes unpleasant misfit. It’s undermined, however, by a depiction of real-life reporter Kathy Scruggs, played with little subtlety by Olivia Wilde, that makes her an unrepentant villain wiling to trade sex for information. It’s a choice so thoughtless it threatens to throw off the whole film.

Richard Jewell was preceded by a much more successful film in the same vein, however. In 2016’s Sully, Tom Hanks stars as Chesley “Sully” Sullenberger, the airline pilot who landed a disabled plane on the Hudson River in 2009. There’s an easy way to tell this story, particularly with Hanks as the lead, a simple, straightforward version that sends audiences out cheering as America’s most likable movie star steps into the shoes of one of its easiest to admire heroes.

Sully isn’t that. Working from a screenplay by Todd Komarnicki, Eastwood uses the incident as a focal point as the film loops around in time, playing and replaying the narrowly averted catastrophe in fragmented and alternate forms as Sully is forced to relive what happened by a hostile panel of National Transportation Safety Board investigators. That conflict is almost entirely bullshit exaggerated to cartoonish proportions (and another example of Eastwood’s distrust of government and authority). It doesn’t matter. Sully is gripping as the story of an ordinary man who does the right thing under extraordinary circumstances, and finds himself still haunted by what might have happened.

A kind of cosmic flip side to Sully, The Mule tells the story of an ordinary man who does the wrong thing under extraordinary circumstances and only comes to be haunted by it later. Eastwood turns it into a story of regret, but only after showing nonagenarian drug trafficker Earl Stone having the time of his life when he crosses over to the dark side. Stone is ultimately brought back down to earth by the law and his own neglected familial responsibilities, and the film ends on a pensive note that leaves him to consider all the choices he’s made and all he’s done wrong along the way. It would have been a fine note for Eastwood to end his career on, both as a director and a filmmaker. But so would Gran Torino, or Unforgiven, or even Space Cowboys, all stories of men coming to realize their time has passed and pondering what that means. Eastwood keeps making valedictory gestures, but it’s turned into a long and increasingly unpredictable goodbye.

Which brings us to Cry Macho, Eastwood’s latest, a film whose daring comes from its smallness, gentleness, and willingness to suggest maybe the tougher-than-tough guys Eastwood made a career of playing had it wrong all along. Eastwood stars as Mike Milo, a former rodeo star who’s survived family tragedies and personal misfortune but landed on the other side of them as a half-broken man. He’s stirred from self-pity when his former boss Howard (Dwight Yoakam) hires him to retrieve Howard’s 13-year-old son Rafo (Eduardo Minett) from Mexico, where he lives with his wealthy, neglectful mother. Once there, Mike finds an abused kid so obsessed with machismo he’s named his fighting rooster “Macho.”

There’s less of the Mule madness that delighted Davidson and Mulaney here. Eastwood’s character does turn down the advances of a much younger woman and throw a couple of punches, but he ultimately settles into a sweet romance with Marta (Natalia Traven), a woman old enough to be a grandmother (though still considerably younger than Eastwood), and shows Rafo there’s more to life than toughness by example. Cry Macho features a few flashes of action and tension but even more moments of Mike calming horses and tending to injured and ill animals. (Eastwood chuckling as he tells a pig it needs to lose a little weight is worth the price of admission alone.)

It’s a charming film, based on a 1975 novel that Eastwood almost adapted back in the late-’80s–that’s how long he’s fit into the aging tough guy mold. It’s also quietly radical, and made even more so by Eastwood’s age. Not unlike Martin Scorsese’s The Irishman, it’s the sort of film made by someone wondering, when he’s far closer to the end than the beginning, what it all meant and what truly matters. What, in the end, was the point of all those fistfights and showdowns and gun battles if you can’t sleep at night and there’s no one who loves you or remembers who you used to be?

Eastwood finds a little more hope than Scorsese, and if Cry Macho were to be his swan song, it would be a lovely way to bow out. But, given that it’s Eastwood, he’s probably not thinking that way. If we’re lucky we’ll get another just as unpredictable decade as he closes in on 100.

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