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

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.

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