The Long, Long Goodbye of Clint Eastwood

I won’t reveal how The Mule ends, but the new film from Clint Eastwood features a moment that’s meant to be a sendoff of sorts for the main character, an aging horticulturalist named Earl. Earl’s a regular guy — he fought in the Korean War, raised a family, followed the rules — but when his flower business goes belly-up thanks to the internet, he’s desperate for money. That’s when he stumbles into a job as a drug courier for a Mexican cartel, which is seeking a driver who won’t raise suspicion. (In other words, they want an old white dude.) Power struggles within the cartel and an encroaching DEA investigation (led by Bradley Cooper’s hotshot agent) threaten Earl’s safety and freedom as he tries to stay a step ahead of everyone. With danger looming around every corner, this octogenarian is looking for a way out.

The Mule’s valedictory spirit isn’t new for Eastwood. The Oscar-winning star turns 89 in May, and for almost a third of his life, he’s been making films that cast him (or surrogates) as lone-wolf characters saying farewell to the world they once knew. It’s become one of Eastwood’s trademarks, as Variety critic Guy Lodge recently noted:

For most viewers 40 or younger, Eastwood is a guy who’s perpetually been saying goodbye. And it started with the movie that many consider his crowning achievement. 1992’s Unforgiven, a revisionist Western that critiqued the genre’s violence and mythmaking, felt like the former Man With No Name’s attempt to close the book on his remarkable career. At the end of that movie, Eastwood’s gunslinger character is seen in the distance silently standing at his wife’s grave — he’s more monument than man. The sun literally sets in the background. If Eastwood wanted the perfect swan song, Unforgiven was it.

Instead, Eastwood kept going, although he’s often dealt with finality in his subsequent films. His adaptation of The Bridges of Madison County was about a passionate affair that cannot last. His starring role in Wolfgang Peterson’s In the Line of Fire found him playing a disgraced, aging secret service agent who wants to make amends for a past failure. In Million Dollar Baby, he’s an aging trainer seeking redemption. His World War II drama Letters From Iwo Jima concerned a Japanese general (Ken Watanabe) looking back on his life as his end is nigh. Hereafter was about a group of characters impacted by death. And American Sniper celebrated a soldier (Bradley Cooper) who responded to harrowing circumstances bravely, his life ending in tragedy.

In each of these films, and others, Eastwood suggests that how we leave this world defines our existence. His characters are often flawed, but they’re seeking the perfect high note to end on — as if a well-executed farewell can rewrite the past. It’s the mindset of someone a bit older, with plenty of experiences under his belt, as well as regrets, who wonders what his life will look like once it’s over. When we’re young, the road spreads out far ahead of us, limitless. Later, though, that road feels shorter, with few surprises and possibilities.

That’s the road that Earl travels as he drives from Illinois to different parts of the country to make his drops for the cartel, and the repetition of his journeys have an obvious metaphorical tinge to them. Earl doesn’t have much in his life — his wife left him, his kid hates his guts, he’s broke — and he’s not too fond of newfangled things like millennials and the internet. There’s no glorious sunset in sight.

Earl is the very model of a modern Clint Eastwood character, a spiritual cousin to Gran Torino’s Walt, who’s also a Korean War veteran who’s pretty crotchety about everything. (Unlike Walt, though, Earl is based on a real person, Leo Sharp, who was the subject of a 2014 New York Times piece.) If Earl isn’t racist, per se, he’s nonetheless the type of older guy who hasn’t learned you shouldn’t call black people “negroes” — and he’s a little too chummy with the Mexican help at his flower shop, making ethnic jokes that ought to embarrass him but don’t.

If you find a guy like Earl objectionable, well, that’s your problem. Eastwood has always prided himself on being a man who does what he damn well pleases — sometimes to his detriment. Have we forgotten that he talked to a chair at the 2012 Republican National Convention? He hatched that kooky idea minutes before walking on stage: “I thought, ‘I’ve got to come up with something different.’ So I just started working on it backstage. Then they were calling my name, and I said, ‘Just give me a chair.’” And for those who thought Eastwood humiliated himself in that moment, his response was curt: “Some people loved it.”

For Eastwood — and, I suspect, a lot of his fans — that stubborn to-thine-own-self-be-true attitude is a badge of honor, a principled resistance to the shifting tides of a fickle culture. A longtime Republican, Eastwood evinced sympathy for Donald Trump during the 2016 presidential campaign, telling Esquire, “[H]e’s onto something, because secretly everybody’s getting tired of political correctness, kissing up. That’s the kiss-ass generation we’re in right now. We’re really in a pussy generation. Everybody’s walking on eggshells. We see people accusing people of being racist and all kinds of stuff. When I grew up, those things weren’t called racist. And then when I did Gran Torino, even my associate said, ‘This is a really good script, but it’s politically incorrect.’ And I said, ‘Good. Let me read it tonight.’ The next morning, I came in and I threw it on his desk and I said, ‘We’re starting this immediately.’”

But no matter how much his back-in-my-day stance means to communicate toughness, it’s also self-pitying, and his films often defensively justify an inability to change with the times as an indication of one’s own strong moral foundation. Eastwood’s protagonists stand defiant, despite being out of step — and so his movies’ need to end with that proverbial walk into the sunset suggests an ennobling of these characters, a sanctifying of their ultimate rightness. They don’t require a happy ending, exactly, but their final moments have to adorn them in honor. We have to leave the film thinking well of them.

That’s why The Mule’s ending is so interesting. Again, I won’t reveal anything, but although Earl has the potential to be a get-off-my-lawn kind of guy, the movie seems far more ambivalent about his ultimate rightness. He makes mistakes, and he ends up paying for them. The Mule argues that even someone like Earl can still change — and needs to.

“Everybody thinks older people never learn anything — only school kids and young people,” Eastwood said recently. “Older people, if they keep their mind open, can be just as interested in improving and learning and new knowledge as they go along.” With The Mule, Eastwood seems to be essaying his own ending — one he’s been crafting and rewriting for decades now. No matter all the accolades he’s accrued over the years, his movies grapple with what honor and legacy mean, as if any of us can dictate how we’re remembered once we’re gone. That paradox adds an unexpected poignancy to Eastwood’s films — he, like his characters, is terrified by the lack of control he ultimately has.

One day, Clint Eastwood will die. Until then, he’s trying to master that final fade out.

Here are three other takeaways from The Mule.

#1. Clint Eastwood’s not a half-bad singer.

We now think of Eastwood as a beloved elder statesman of Hollywood — a pillar of the industry — but that wasn’t always the case, especially when he was derided early in his career for being “just” a cowboy actor thanks to Rawhide and his spaghetti westerns. (The jokes would only continue when Eastwood costarred with an orangutan in Every Which Way But Loose.) But as he became a respected actor and Oscar-winning director, Eastwood’s reputation changed. This only makes his brief flirtation with singing even stranger.

A few years ago, Slate’s Forrest Wickman put together a handy guide to Eastwood’s musical career, which started in the early 1960s with Rawhide’s Clint Eastwood Sings Cowboy Favorites. “It was done in one night,” Eastwood once recalled of the album, adding, “It was an odd choice of things. … It was somebody else’s idea. If it was my idea, I’m sure as hell ain’t taking credit for it.”

Technically, Eastwood’s voice isn’t bad, but the idea of Mr. Gruff emoting in such a sincere way is incredibly odd. The vulnerability in his voice strips away his cool.

But if Cowboy Favorites embarrassed Eastwood, he didn’t let that stop him. Infamously, he starred in 1969’s Paint Your Wagon, a big-screen adaptation of the hit Broadway musical, which received terrible reviews. (“The fact is, Paint Your Wagon doesn’t inspire a review,” Roger Ebert wrote in his pan. “It doesn’t even inspire a put-down. It just lies there in my mind — a big, heavy lump.”) He had much bigger success with his duet with Merle Haggard on “Bar Room Buddies,” which went to No. 1 on the country charts in 1980. (“Well, I think you can say that Merle Haggard had a hit and sort of dragged me along,” Eastwood said in 1985. “I was never terribly knowledgeable about country music.”)

No matter Eastwood’s vocal limitations, he’s always been interested in music. He played piano as a kid, and when he started directing, he’d occasionally compose songs for their soundtracks. For Gran Torino, he sings over the film’s ending credits, his voice a husky whisper.

So while Eastwood may be a little sensitive about his singing, his musical DNA remains in his films. “A lot of the pieces I write are sort of Chopin-esque,” he said in a 2008 interview. “I think that’s one of the biggest influences I have. … I usually play every day. I’m usually writing something every day. I don’t play to perform, though I suppose I could work out some things if I needed to.”

Dirty Harry: Live and on Stage does have a nice ring to it.

#2. Bradley Cooper’s ‘A Star Is Born’ was almost Clint Eastwood’s ‘A Star Is Born.’

There had been three previous film versions of A Star Is Born before director/actor Bradley Cooper released his remake this fall. If that seems like an excessive amount of Star Is Born movies, just remember that we almost had another one years earlier, directed by Clint Eastwood. And it might have happened if Beyoncé hadn’t gotten pregnant.

Back in 2011, Eastwood signed up for the remake alongside the singer after an earlier attempt by director Nick Cassavetes had fallen through. (“I didn’t think I would ever get the opportunity to be the star,” Beyoncé said later that year. “I met with Clint and I was so nervous, and I know that it is the biggest opportunity of my life.”) The trick was figuring out who the male lead would be. Everybody from Johnny Depp to Tom Cruise was approached about the project, but then the film hit a snag when Beyoncé exited after she announced her pregnancy in 2012. It was during this limbo period that Eastwood thought of Cooper, who turned him down. “I just knew I was too young,” Cooper explained this year. “I felt like I hadn’t lived enough.”

Eventually, Eastwood left the film — he and Cooper went on to make American Sniper together — and Cooper decided he wanted to direct A Star Is Born himself. The movie, in which Cooper costars with Lady Gaga, has been an enormous commercial and critical hit, and it looks to be a major Oscar contender. Eastwood, who saw the film early, approves, saying this week, “It’s terrific. … I’m proud of him.”

We’ll have to wonder what an Eastwood Star Is Born would have looked like, although he did get a shot at a musical a few years back with Jersey Boys. That didn’t turn out too good.  

#3. So, who was the real Leo Sharp?

The Mule is based on an actual drug mule, Leo Sharp, whose arrest in 2014 generated local news coverage. This segment on the day of his sentencing — which was the same day he turned 90 — is deeply sad. Make sure you stay until the end for the final, brutal kicker.

Sharp didn’t go through with his threat to take his own life — he died in 2016 — but the novelty of the man’s twilight-years occupation attracted the attention of journalist Sam Dolnick, who wrote about Sharp for The New York Times. Among the interesting tidbits in Dolnick’s profile, this longtime horticulturist was apparently a pretty cool dude in the world of day-lily growers.

“The people who do lilies are way cooler than other plant people,” an Illinois gardener told Dolnick. “He was just a stud. He just had the air. He had 70-year-old swagger.” Funny enough, this is brought up a little in The Mule, where we see Earl enjoying himself with cartel prostitutes. (If you’ve been waiting your whole life for an Eastwood three-way on screen, The Mule is the film of the year.) But among the areas where Sharp’s life and the film differ, Earl doesn’t have dementia, which appears to have significantly taken its toll on Sharp near the end of his life.

Dolnick recounts the day that Sharp was sentenced, and it’s rather upsetting: “He addressed the judge in a soft, croaky voice. ‘I’m really heartbroken I did what I did,’ he said. ‘But it’s done.’ Then he made one, final, strange plea. If he could stay out of jail, he proposed paying off the $500,000 penalty he owed the government by growing Hawaiian papayas. ‘It’s so sweet and delicious,’ he said, his voice nearly breaking.” The judge denied the request, sentencing Sharp to a three-year term. Sharp was released a year later. He was dead a year after that.

This week, Dolnick reflected back on his time reporting on Sharp, whom he only met once. “[A]s a journalist, I was never able to crack Leo Sharp,” he writes. “I spent months chasing the central question at the center of my story: Why did he do it? Was he a dupe? Was he a con man? Was he a criminal mastermind? I have my theories. But journalism can take you only so far. … Even with all my reporting, I couldn’t fully tell you what motivated Mr. Sharp. I don’t think anyone could, not even Leo Sharp himself.”

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Tim Grierson

Tim Grierson is a contributing editor at MEL. He writes about film and pop culture for Screen International, Rolling Stone and Vulture.