In Appreciation Of: Clint Eastwood At 90

For nearly 60 years, one man has stood tall in Hollywood, creating performances and films that have collectively enriched our cultural imaginations. He is Clint Eastwood, an icon of cinema and for a time the epitome of rugged masculinity.

Whether it is in front of or behind the camera, Clint Eastwood as the actor, director, producer, and musician, continues to show that even after all this time his work continues to leave deep impressions on us. Beneath the seemingly tough exterior lies a prolific artist of great talent, offering movie lovers a rich catalog of films that have forever altered popular culture. 

In celebration of his 90th birthday on May 31st, here is a look back at some of the best, most iconic, and ultimately most affecting works from this enduring star and giant of the movies.

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Dollars Trilogy (1964-1966)

Arriving years removed from the heyday of the classic Western, Sergio Leone’s Dollars trilogy revitalized the genre. Starring then relative unknown Clint Eastwood as “The Man With No Name”,  the series paid homage to the classic roots of the Western while redefining elements that have since gone on to become synonymous with the genre.

Adopting a looser take on the classic portrayal of cowboys Leone allows for the flexibility of the cowboy image beyond traditional good guy or bad guy designations. Such flexibility coupled with a now-iconic Ennio Morricone score and emphasis on the cinematic elements rather than narrative-driven plot combine for a uniquely impactful experience. The trilogy is as much a homage to the classic work of John Ford and Wayne as it is to Akira Kurosawa’s samurai films incorporating similar principles of editing and framing in conveying the bloodshed.

For Eastwood, it is his breakout role, one that would go on to define his minimalist style in front of the camera even into his twilight years. The archetype of the strong but silent type caked in layers of blood, sweat, and grime provides the template for anti-heroes to this day. Despite coming years after the peak of the genre, Eastwood undoubtedly stands right along with the likes of John Wayne in terms of defining what a Western is. – Nate Lam

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Dirty Harry (1971)

“You’ve got to ask yourself one question: Do I feel lucky? Well, do ya punk?” 

 A landmark of 1970s neo-noir and the police thriller genre, Dirty Harry not only cemented Eastwood’s rising star power but affirmed a new type of cop movie for a new age. While elements of the film would certainly be considered politically incorrect today, its lasting effect lies with its no-nonsense, unfiltered, and ultimately charming protagonist, Detective Harry Callahan. 

Coming off his success with Sergio Leone’s spaghetti westerns and the World War II film Kelly’s Heroes, the emergence of Dirty Harry further added to the image of Clint Eastwood, the man’s man. Taut, gritty, suspenseful, and even humorous, the movie remains an entertaining time capsule of San Francisco in the 70’s and the changes in attitudes following the “free love” of the 60’s. 

Featuring an effectively menacing and memorable score from composer Lalo Schifrin, the inaugural film in the Dirty Harry series is without a doubt an American classic, rightfully chosen for preservation in the Library of Congress. And then of course there’s that quote….one that most audiences will recognize, even if they have not seen the film itself. – Michael Vecchio

Escape from Alcatraz (1979)

The infamous federal penitentiary at Alcatraz Island in San Francisco Bay has long been the subject of public fascination, and it has indeed inspired a number of films. With Escape from Alcatraz director Don Siegel (who reunited with Eastwood after Dirty Harry) recounts the true story of inmate Frank Morris who alongside a group of fellow prisoners orchestrated a successful escape from the prison’s walls, only to disappear in the frigid waters of the Bay. Eastwood is quiet and reserved in the role of Frank Morris, and in fact the film features very little dialogue at all; instead there is much use of the silence and natural sounds of prison life to create a portrait of institutionalism. 

As Morris and his conspirators prepare their plan of escape, audiences are met with much tension and uncertainty. Will the group get caught? How will the hawkish warden (Patrick McGoohan) react? And ultimately, can they survive the trip to mainland San Francisco? Rather than create visceral entertainment, the slow build leads to an intellectual satisfaction that keeps viewers guessing throughout. 

It is not a showy movie, nor does it use Eastwood in an over the top way, and yet Escape from Alcatraz finds effectiveness in its slow and contemplative approach. This allows its star to still present a tough guy image without being loud and obnoxious, in the process becoming one of the best prison films ever made. – Michael Vecchio 


The Outlaw Josey Wales (1976)

While his work with Sergio Leone remains Clint Eastwood’s best known Western films, he has indeed appeared in a number of acclaimed and important movies in this dying genre, including Hang ‘Em High (1968), High Plains Drifter (1973) and 1992’s Unforgiven (see below).

The Outlaw Josey Wales is then not only a great Clint Eastwood movie but one of the very best Western films of the last 50 years; as the titular antihero, Eastwood capitalizes on the aura of masculinity that initially brought him fame, all the while creating a compelling story of revenge and redemption. Coupled with beautiful and evocative cinematography by Bruce Surtees and a wonderful supporting performance by Chief Dan George, this movie is everything a fan of the Western could ask for. 

Gun battles, horse riding, vengeance, blood, and stunning vistas galore, Eastwood indicates that he learned well from the master Leone in crafting a movie that honors the genre’s roots while forging a new path for stories set in the Old West. In short, The Outlaw Josey Wales is a terrific entry in the pantheon of Western movies, deservedly selected for preservation in the Library of Congress. – Michael Vecchio

Honkytonk Man (1982)

Based on the life of country music pioneer Jimmie Rodgers, Honkytonk Man is not a showy piece, filled with all the glitz and glamour of a country star’s life. Instead, it is an emotionally mature examination of one man’s last attempt at glory. 

As the fictional Red Stovall, Eastwood is a mix of sensitivity and toughness; plagued by tuberculosis that is slowly killing him, he refuses to let the disease write the final chapter of his life story. Accompanied by his young nephew (Kyle Eastwood, Clint’s son), Red knows he may not have much time left, but that is not going to stop him from leaving behind a legacy of musical excellence. 

With a compelling performance and a respectful directorial eye for the time period and the country music genre, Clint Eastwood’s Honkytonk Man may be lesser known amongst his films but is surely amongst his finest efforts on both sides of the camera. – Michael Vecchio

Unforgiven (1992)

If Leone’s Dollars trilogy gave birth to the stoic rough-cut image of Eastwood he is most commonly associated with then Unforgiven is the film that lays it to rest. In what he claims to be his last foray into the Western, Eastwood takes on the mantle of Will Munny – an ex bounty hunter turned pig farmer enticed to do one last ride in the name of vigilante justice (and a handsome cash reward). On paper, this appears to be an Eastwood led farewell tour down his greatest hits and though he does oblige by playing all his trademarks (the steely stares, the gruff line readings, and of course the quick drawing gunmen) he is also willing to deconstruct the romanticism surrounding the genre.

As such Unforgiven acts as a eulogy as given by a graying Eastwood whose face once afforded a rugged handsomeness in his iconic poncho and cowboy hat now replaced with the wrinkles of time and the scars of battles gone by. Fitting perhaps that it is given by the man who kept the genre alive as he broaches the harsh lifestyle of the cowboy, the questionable image of masculinity in modern contexts and the moral toll the act of cold-blooded killing takes on a person beyond the imminent danger. – Nate Lam

The Bridges of Madison County (1995)

Chronicling the tender four-day love affair between a lonely housewife and a traveling photojournalist, The Bridges of Madison County (based on the novel of the same name), does not seem like a typical Clint Eastwood film; after all there is no machismo or dominant alpha male present, but rather a sensitive, soft-spoken, and caring man for him to personify. Yet here is Clint Eastwood again displaying his versatility, and despite not having an abundance of these types of roles, shows that if he wanted to he could indeed be a moving lead in the romance genre. 

With the role of Robert Kincaid, gone is the tough guy with a reluctance to show emotion; instead, we have a delicate and emotional spirit, who meets his true soul mate in the form of Francesca Johnson (Meryl Streep). Although only together for a weekend, what develops between the two defines what it means to find true love. 

Slow-paced, contemplative, and emotionally rewarding, The Bridges of Madison County is a quietly forceful masterwork. As director and star, Eastwood showed with fine craft that the image of the “no tears” man was just one side of his very capable performance toolbox. – Michael Vecchio

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Million Dollar Baby (2004)

The latter stages of Eastwood’s career have seen him morph from the rugged gunslinger to the muted observer. As the world shifts from the antiquated traditionalism that he became a star in, Eastwood has adapted contributing to his extended longevity while providing an interesting divide in his oeuvre. His post-millennium work both in front and behind the camera has been steadfast in his conservative views and hearty American nationalism, an identity that tends to polarize his audiences but where his more recent work (Sully, American Sniper) has been rooted in a sense of heroism, the subject matter in Million Dollar Baby is anything but heroic.  

What begins seemingly as a by the numbers sports movie in the vein of Rocky (another symbol of American triumph against all odds) with Hilary Swank as the down on her luck boxer and Eastwood as her reluctant disgruntled “too old for this shit”  trainer transforms into an effective statement on morality, ethics, and greed. Where other films in Eastwood’s catalog like American Sniper also have something to say, in this case pertaining to the US participation in war and post-traumatic stress disorder, they are often buried within the desire to present these figures as larger than life heroes. Million Dollar Baby’s stance is abundantly clear and it is such a stance that allows the film to deliver its final knockout blow that wins over even Eastwood’s staunchest critics (albeit a punch stuffed with enough emotional sentiment to make Spielberg blush). 

Evidently the film had its desired effect taking home multiple awards including Best Picture and Best Director for Eastwood.  Perhaps more importantly though, Million Dollar Baby demonstrates Eastwood’s ability to defy expectations. Classic roles over a 60-year career have established a myriad of labels to the man but that capacity to demonstrate a new trick from time to time is what makes him a fascinating figure to watch. – Nate Lam

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Gran Torino (2008)

The first mainstream film to star Hmong actors (an ethnic group from Southeast Asia), Gran Torino features the typical badass Eastwood performance, who showed that even as a senior he could be quite intimidating. But beyond the gruff and bigoted central character of Walt Kowalski, Gran Torino is ultimately about the need for tolerance and redemption, reminding the audience that no one is necessarily too old to change. 

Although Walt remains a largely discriminatory and antiquated man, struggling to find meaning in an ever-changing modern world, a relationship with his young Hmong neighbor Thao begins to transform his racist mindset. Attempting to protect the teenager from a vicious street gang, Walt does not exactly display affection in the most traditional way, but in his own rough manner gives Thao and his family an unexpected gift: hope for a better tomorrow. 

As the consensus on Rotten Tomatoes states, Gran Torino “is a humorous, touching, and intriguing old-school parable.” With the message that hearts and minds of stone can change, and that fighting for something noble can lead to that very change, it is a movie that although like its central character is not perfect, strives to generate a wider conversation on the importance of erasing the barriers built between us. – Michael Vecchio

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The Mule (2018)

With The Mule, Eastwood returned to the director’s chair and also stars as the eponymous drug trafficker (the first time he performed both duties since 2008’s Gran Torino) in a film whose heart is centered around themes of nostalgia, redemption and confronting the past. This is very much a movie built around Clint Eastwood who delivers a sensitive and charming performance and is perhaps not surprisingly, quite spry in the title role. 

 Like the character Earl Stone, Eastwood acknowledges his age and the limitations it brings, realistically creating a portrait of a man out of his depth; there is nothing artificial in his performance, for indeed what we see is an old man playing an old man with sincerity and charm. 

For fans, The Mule will not be seen as a groundbreaking classic in his vast filmography, but it is still very much a stirringly solid entry into his canon of work. Anchored by his assured direction and undeniable star power, even at this elderly age, the movie succeeds as an entertaining and thought-provoking viewing. – Michael Vecchio


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Flags of our Fathers/ Letters from Iwo Jima (2006)

The decisive American victory at the Battle of Iwo Jima in 1945 set the stage for the end of the Pacific Theatre in World War II; in 2006 Clint Eastwood fashioned a pair of films that aimed to spotlight this ever-important and savage battle, Flags of our Fathers and Letters from Iwo Jima. A unique approach to filmmaking, Eastwood essentially told the same story in two films, but from the American perspective in one and the Japanese one in the other. 

In the case of Letters from Iwo Jima, audiences not only see the plight of the Japanese people and the consequences of rigid ultranationalism but begin to understand that at the human level, these so-called enemies were just as scared, vulnerable and plagued with guilt as their American counterparts

The brilliance of Eastwood’s two films is their focus on the humanity at the core of such wars, and the acknowledgment that good and evil is not simply one-sided. Indeed viewing these films gives no indicators of who was “good or bad”, but rather a sad look on the continued absurdity of armed conflict and the souls who paid with their lives for it. – Michael Vecchio

Changeling (2008)

Poignant, tragic, and even infuriating Changeling is a well-rounded work of historical drama, brought to life not only by Eastwood’s sensitive direction but a bravura and emotional lead performance from Angelina Jolie in an Academy Award-nominated role. 

Based on a series of child abductions and murders in 1928 Los Angeles, the film tells the story of young mother Christine Collins and the disappearance of her 9-year-old son Walter; initially fear turns to joy when the LAPD announces they have found the boy unharmed. When Christine is reunited with him however, it is clear that the boy whom the police claim is Walter is really someone else. Thus begins a protracted battle between the LAPD and the ailing mother, desperate to find her real son as the authorities continue to make her question her own sanity. 

Although Changeling deals with distressing material, it is constantly stubborn in its message of hope; Christine may realistically know that she will never see Walter again, but her hope keeps her going. It is precisely this hope that moves all those who help her, fighting not just for Walter but for justice and truth to prevail. With its themes on the dangers of corruption (political and within police ranks), the rights of women, and crimes against children, Changeling is ultimately an intelligently layered film that undoubtedly leaves a profound impression on its viewers and confirms Eastwood’s prowess as a cinematic storyteller. – Michael Vecchio 

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