The Best Movie Ever: Clint Eastwood

The Best Clint Eastwood Movie Ever

Clint Eastwood is one of the few remaining motion picture icons we have left: an unforgettable on-screen presence and a hardworking, celebrated filmmaker whose latest movie – Jersey Boys, opening this weekend – will be his 33rd feature film to date. He has starred in and/or directed some of the most important, groundbreaking, critically-acclaimed and financially successful movies in the history of the cinema. But here at Best Movie Ever it's our job to look at Clint Eastwood's massive filmography and decide, once and for all, which of his films is the best.

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Joining us in our task are CraveOnline's intrepid film critics William Bibbiani, Witney Seibold, Fred Topel and Brian Formo, who have each selected a different film from a different decade as Clint Eastwood's masterwork. They each have their reasons, as you shall soon see below. Take a look at their arguments and then vote for your own Clint Eastwood favorites at the bottom of the page, to help us finally single out The Best Clint Eastwood Movie Ever.

William Bibbiani:

High Plains Drifter

Clint Eastwood the actor may be known for  confident, steely performances that solidified the American ideal of a contemporary (now, seemingly historical) hero, but as a director he's always come across as a deconstructionist. He set himself up as an icon only to repeatedly tear himself down, finding within that macho exterior something lacking. Sometimes he located an unexpected tenderness, but his greatest accomplishment may have been when he looked within the façade of the western ideal he himself to beautifully typified and identified something truly vile. You could argue that The Good, The Bad and the Ugly is a better western, and you could argue that Unforgiven is more classically complex, but High Plains Drifter still feels like his most singular contribution in front of and behind the camera.

It is a simple set-up: the town of Lago's sheriff is dead and the culprits are eventually coming back. Later, a man with a suspicious but non-specific resemblance to their fallen protector arrives, and makes the town – in the common parlance – his bitch. He beats, murders and even rapes his way into the position of the community's alpha male, so much so that when danger finally does return, no matter how much they fear this mysterious stranger they turn to him for protection from the outlaws. He agrees in return for a fascistic control over the townsfolk, which takes the form of further bullying and increasingly maddening demands, like painting the whole town red and renaming it "Hell." 

There's a simple emotion that comes across throughout High Plains Drifter that nevertheless makes it feel atypically personal compared to many other entries in the western genre: disdain. Whether Clint Eastwood was actively trying to destroy his image I cannot say, but here he takes a familiar tale and warps it into a grotesquery of violence and sadism, and dares to take a stand and claim that his most "anti" hero on record may be entirely in the right, even as he challenges all preconceived notions of the noble American frontier. High Plains Drifter is an angry but clearly calculated outburst that became – to me, at least – his most distinctive film. I would even go so far as to say that it is the best Clint Eastwood movie ever.

Brian Formo:


Clint Eastwood has been involved in more than just a fistful of good-to-great films. He's so iconic in the Sergio Leone spaghetti western trilogy that his method of minimal growl-speech has been adopted by seemingly every male hero/anti-hero from Kurt Russell's Snake to Christian Bale's Batman. Behind the camera he's given us Play Misty for Me, The Outlaw Josey Wales, Unforgiven, A Perfect World, The Bridges of Madison County, Mystic River, Million Dollar Baby, Letters From Iwo Jima and even deconstructed his own persona in Gran Torino. For the "Best Clint Eastwood Movie Ever", however, I'm going to choose a film where Eastwood deconstructs a different, electric persona through his own lens: Bird, which could lovingly be re-titled The Outlaw Charlie Parker.

Western films and jazz music have an engine for newness that runs parallel. They've both had to be re-invented to stay relevant. The western story moved from the hero who holds down order in a town, to the anti-hero drifter who passes through town with his own burdens and secrets. Then it shifted to modern areas of Mexico, Texas, etc. where rifles, saloons and ten-gallon hats weren't out of place. And then it finally appropriated into modern police procedurals. Jazz went from swing, to beebop, to free jazz and then into hip-hop samples.

It's obvious in Bird that Clint Eastwood loves Charlie Parker's music. Clint Eastwood is a "failed" jazz musician in that his own piano career never took off, but his son, Kyle, is an accomplished jazz bassist. In Bird, his impatient gunslinging fans might moan that he films Parker's (Forest Whitaker) performances for too long. That's a ridiculous notion. Parker's fire came from inside. His performances were his preferred vessel to drift, alone.

in Bird, Eastwood and Whitaker made a biopic of a great artist with a drug addiction (Parker became addicted to morphine after an accident as a teenager and later substituted it for heroin) but they brilliantly sidestep the simpler film of greatness squandered. Instead, Parker's addiction is shown as a burden that he feels he must carry as he drifts, much like the guilt of an outlaw who wanders in isolation from town to town, saloon to saloon. Eastwood's career has shown a loving gravitation to the drifter. But his best achievement might have been showing a drifter who drifts without moving. Now, that's jazz.

Fred Topel:

In the Line of Fire

Despite the breadth of Clint Eastwood’s work as an actor and director, this was actually an easy pick for me. It’s not one he directed, and it’s not even one of his landmark westerns. Although The Good, The Bad and The Ugly is an unimpeachable western epic, it’s an Eastwood movie with which I grew up in my lifetime that proved itself the ultimate classic.

I suppose when In the Line of Fire came out, it was a gimmick. Let’s put an aging action hero in the lead and watch him lose his breath running, etc. Eastwood carried the part with grace and this was long before The Expendables. John Malkovich is a national treasure for his landmark villain performance here. He’s seductively menacing in his speech, and amazingly we feel suspense for him when he drops his bullet at the presidential dinner. 

In the Line of Fire remains indubitably watchable 21 years later. There’s only two action scenes, but the phone calls between Malkovich and Eastwood are the real set pieces. Highly quotable lines like “rendezvous with my ass” and “I know things about people” remain part of my vocabulary years later. Rene Russo once again shows she can play with the boys. Though overtly dealing with sexism, that seems about right for 1993 government detail and she was always my hero. This Best Movie Ever pick is dedicated to my childhood best friend Timothy Mummert, whose enthusiasm for In the Line of Fire made it “our” film. 

Witney Seibold:

Mystic River

Even if Clint Eastwood had never acted in any movies, he would still be something of a Hollywood legend. With nearly 40 directing credits to his name, Eastwood has a surprisingly consistent track record. Sure, there are some duds in the bunch (I know no one who is intensely fond of Midnight in the Garden of Good and Evil, for instance), but his sheer volume of output guarantees that at least some of them ought to stick. As an actor, I would say that Dirty Harry is perhaps Eastwood's best film. He embodies the a badass, right-wing segment of the 1970s that could never exist today, and is yet still ineffably cool. But when it comes to his best, most complex, most thoughtful work, I will choose a directorial effort of his. 

As such, I will select Mystic River as Clint Eastwood's best film, which I know is an unpopular choice. (I haven't seen Unforgiven, and you can give me grief for that in the comments section below.) Mystic River is a modern crime epic which is essentially about the small moral turns that lead to the birth of an outright crime lord. When his daughter is killed (perhaps), Sean Penn becomes convinced that the local nutcase (Tim Robbins) is to blame. His quest for vengeance becomes so strong that he begins to ignore evidence to the contrary. But at some point along the way, Penn seems to shift from an obsessed dad hellbent on vengeance into an astute businessman who seems to be increasingly comfortable within a life of crime. 

We've all seen films about crime bosses, but it's rare that we get such a stark, not to mention modern, genesis of the notion. It's a gorgeously dour, beautifully pessimistic dissection of moral decay, all within the bounds of a small American town. Eastwood has always shown a propensity for deconstructing the myth of macho (indeed, isn't that what Unforgiven is about?), and I feel that Mystic River displays a deconstruction of the modern movie crime boss in a way few films of the '00s approached. 

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