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Clint Eastwood Through the Decades

By Ryan O’Toole

With the release of his latest film, Cry Macho, Clint Eastwood has entered his 7th decade in the film industry. At age 91, he has directed 39 films in his long standing career and shows no signs of slowing down. Clint has been a monumental figure in the industry and a constant presence in film for his entire career. The last of his generation, Eastwood continues the classic Hollywood style - a style which was set forth by John Ford and Howard Hawks. He has worked long enough to collaborate alongside these peers, but he’s also been around to witness the emergence of new Hollywood directors, the rise of CGI and blockbuster filmmaking. But, throughout his career, he has seemingly stayed true to himself. He has carved out his own pocket within the industry while constantly reinventing himself throughout his filmmaking.


Below are Clint Eastwood’s 8 essential works that paint the portrait of one of Hollywood’s greatest icons.


The 1960’s: The Good, the Bad and the Ugly


Photo: Mubi — Source


Clint Eastwood technically started acting in the 1950’s, as a role player in 50’s studio films and starring in his own TV show, Rawhide. However, Clint got his first leading role in 1964 with A Fistful of Dollars (1964). This is where Clint cemented himself into the cinematic canon; in Segio Leone’s spaghetti Westerns. Together, they made the Man with No Name Trilogy, A Fistful of Dollars, For a Few Dollars More (1965), and, the pinnacle of their collaboration, Leone’s masterpiece, The Good, the Bad and the Ugly (1966).


Clint’s iconic turn as the Man with No Name in The Good, the Bad and the Ugly catapulted him to stardom and remains one of the most enduring cinematic roles. Contrasting to John Wayne’s idealistic, righteous western characters, Clint Eastwood’s always have a dark underbelly. There is something mysterious and unknowable about Eastwood’s characters which starts with the anti heroes and lone gunman, the Man with No Name.


The 1970’s: Dirty Harry


Photo: The Politic — Source


After becoming a Western icon, Clint Eastwood transposed his antihero into a modern urban setting with the hit film, Dirty Harry (1971), a modern gunslinger who follows his own moral code. Dirty Harry follows Harry Callahan as he tries to catch the murderer based on the Zodiac killer. He is a tough, intimidating force that will stop at nothing to get his man. He has turned the mystery from the Man with No Name into outright violence with Dirty Harry and Harry Callahan remains one of Clint Eastwood’s most memorable roles.


Dirty Harry is a film with a messy history, basically creating the loose cannon cop who would shoot first and ask questions later. Some critics at the time claimed the film was “fascistic, criticizing the film for being too violent and Harry being morally corrupt. This is a criticism Eastwood would try to confront in later entries. The very next film, Magnum Force (1973) almost acts as a condemnation of the idea of a vigilante cop as a way to skirt around the order put in place by the system.


This is also one of Clint’s collaborations with Don Siegel, his biggest creative partner at the time. Together they made 5 films in 10 years including The Beguiled (1971) and Escape from Alcatraz (1979). However 1971, which saw the release of Dirty Harry, also marked a changing point in Clint’s career. He released his directorial debut, Play Misty with Me (1971) and after working with two great directors to craft his image, Sergio Leone and Don Siegel, Clint would soon start to mainly work with his own greatest director for decades to come: Clint Eastwood.


The 1980’s: Honkytonk Man


Photo: Mubi — Source


The 1980’s saw Clint’s continuation from threads earlier in his career — directing two Westerns in the 1970’s High Plains Drifter (1973) and The Outlaw Josey Wales (1976) and continued in the 1980’s with Pale Rider (1985). He also starred in more Dirty Harry movies, even directing the fourth installment, Sudden Impact (1983). — but it also saw him experiment with different genres. He started to make movies outside of the western/action thrillers he was known for with musical biopic Bird (1988) and the military drama Heartbreak Ridge (1986), but it is the criminally underseen Honkytonk Man (1982) that best encapsulates this transitional era for Clint.


Honkytonk Man follows fictional alcoholic singer, Red Stovall, played by Eastwood, as he embarks on a journey with his nephew to get to Nashville and perform in the Grand Ole Opry. Red is a haunted man, seemingly doomed from the start, but he works his way across the country running meeting different people and getting into different situations with his young nephew teaching him life lessons and maturing him along the way, a common theme that appears in later Eastwood movies


The film is set during the Great Depression and is still aesthetically in line with the Westerns that made him. Containing small frontier towns and open landscapes, Clint feels in his wheelhouse, but trying a vastly different style of filmmaking. If his Westerns, High Plains Drifter and The Outlaw Josey Wales were inspired by the works of Howard Hawks, Honkytonk Man is Clint Eastwood’s John Ford movie. Recalling The Grapes of Wrath (1940), Clint balances humor and tragedy in equal measure to create an American odyssey.


The 1990’s: The Bridges of Madison County


Photo: Mubi — Source


The 1990s are perhaps Clint Eastwood’s most fruitful period in his career, successfully making films in a variety of genres, while also offering an introspective look inside the many sides of Eastwood himself. He makes a thinly veiled account of John Huston making The African Queen (1951) in White Hunter, Black Heart (1990), a contemplation on the nature of violence in the Kevin Costner starring A Perfect World (1993), and a conspiracy thriller in Absolute Power (1997). However it is The Bridges of Madison County (1995) that best defines Clint Eastwood in this period.


The Bridges of Madison County shows a softer side of Eastwood. The film chronicles a budding romance between Meryl Streep’s 1960’s housewife and Eastwood’s world weary photographer. It’s a very simple movie focusing on these two characters and, yet, there is a lot of self reflection on Eastwood’s part. It is a film about growing old and about a photographer who isn’t taken seriously, because he is making more commercial work - like covers of magazines. There is a lot of Eastwood in there, being the artist that is being portrayed in the film. But at the same time, there’s a gentle romance between him and Streep that develops throughout the film, and it is absolutely captivating.


The 1990’s: Unforgiven


Photo: The Guardian — Source


I originally wanted to keep this list to one movie per decade, but as I got to the 90s, I loved The Bridges of Madison County too much to not include it. But it is also impossible to talk about Clint Eastwood without talking about Unforgiven (1992). It is perhaps Clint Eastwood’s magnum opus, the centerpiece to a long and storied filmography. If The Bridges of Madison County is a self reflection of Eastwood as an artist, Unforgiven is a self reflection of Eastwood as an icon. It is a direct response to the western image he has crafted over the decades he has been making movies.


Unforgiven is about an aging ex-gunfighter, William Munny, who is pulled back in to do one last job: to seek revenge and kill two cowboys. The film is another contemplation on the nature of violence and the morality of vigilante justice. As William Munny contemplates his violent past and is haunted by those he has killed, it is easy to see Eastwood contemplating the same about his own past. He has made an icon out of the gunslinger who plays by his own rules, but as he is growing older, he is now reflecting on his role in that violence.


Unforgiven is one of the greatest classic westerns ever made, rivaling the best of Howard Hawks and John Ford. If the classic western genre died in the 1970s, Unforgiven is the final nail in the coffin as if to say, “We’ve done it. We’ve reached the top of the mountain and no one will top this” Unforgiven is the finest send off that Eastwood could ever hope for and remains the last classic western he has made. And it would be a fitting swan song for Eastwood as an artist, an aging actor-director who was pulled back in to do one last job. And yet, Eastwood has continued to tirelessly keep working, making 23 more films since Unforgiven.


2000’s: Mystic River


Photo: The Telegraph — Source


The 2000’s saw a change in the way Clint Eastwood’s films were perceived by the public. The more commercial adult dramas he was making started to align more with the kinds of films the Academy enjoyed. For a lot of people, this era in Clint’s filmography will be remembered as the Oscar bait era. He won his second Best Picture and Best Director trophy for Million Dollar Baby (2004) — his first being Unforgiven. And in this era, he made his WWII duology Letters From Iwo Jima (2006) and Flags of Our Fathers (2006), Gran Torino (2008), and Invictus (2009). But I think the best of Clint’s Oscar movies is his first, Mystic River (2003).


Mystic River is a mystery crime movie about three men who grew up together and their fractured lives. The story centers around the murder of one of the men’s (Sean Penn’s Jimmy Markum) daughter - a role which won Penn his first Best Actor Oscar. It is another Clint film about the nature of violence, a consistent theme in his oeuvre, and the haunting effect it has on those it touches. It is a film about broken men and broken families as they confront their past. On its surface, it may seem similar to a lot of Clint’s earlier movies, and yet, the style is completely different. It is not an action packed movie like the Dirty Harry movies, or a classical Hollywood film like Unforgiven. It is a haunted, stark movie about trauma and grief that pushes Clint in an entirely new direction.


2010’s: Sully


Photo: The Hollywood Reporter — Source


Clint Eastwood’s Oscar bait era continued into the 2010’s with films like J. Edgar (2011) and American Sniper (2014). And it felt like audiences had grown a little stale of this kind of Clint Eastwood movie. He was no longer making the commercial adult dramas he had found success with in the 1990’s instead choosing to make more prestige dramas. And then, in 2016, Clint Eastwood released, Sully, a ripped-from-the-headline movie about pilot Chesley “Sully”Sullenburger, his forced water landing on the Hudson, and the investigation that followed.


Sully was a return to form for Clint Eastwood, returning to the Howard Hawks school of classical Hollywood. Eastwood, along with a brilliantly cast, stoic Tom Hanks, is able to craft a deceptively simple, solid adult drama. It is a story that finds the extraordinary in the ordinary. Sully is a man that was just doing his job to the best of his ability and is later questioned to no end on how he could have done better. Hanks is brilliant in this as the humble, hardworking pilot full of gravitas, but it is the sturdy framework constructed around him that gives this film the life it needs. Eastwood, like Sully, is a no nonsense man, simply doing his job to the best of his ability.


Sully acted as a bit of a career revival for Clint Eastwood and started his run of well crafted dramas like The Mule (2018) and Richard Jewell (2019) that follow. He reentered people’s lives and offered a new era for audiences to love.


2020’s: Cry Macho


Photo: ABC — Source


Now in his 7th decade, Clint is still reckoning with his own image and Cry Macho (2021) acts as a career retrospective for an aging Clint Eastwood. Cry Macho is a movie about an old ranch hand, Mike, who is hired by his old boss to go into Mexico and bring back his kid. Clint plays Mike who bonds with the kid, Rafo, on their journey back to the United States as they evade the police and Rafo’s mother who try to take Rafo back. Along the way, Mike meets a Mexican diner owner, Marta, and a romance blossoms between the two of them. It is a near plotless movie that is really about Mike and his relationship with Rafo and Marta, examining the aging cowboy as he tries to settle down.


Cry Macho is a great summation of a lot of Eastwood’s career, combining the western aesthetic and iconography from The Good, the Bad and the Ugly and Unforgiven, the road movie elements from Honkytonk Man and the gentle romance from The Bridges of Madison County. It is a gentler self reflection over something like Unforgiven, choosing long stretches of tranquility over violence. And while it is not an entirely new zone for Eastwood to be operating in, it is a great culmination to a decades long career.


I have no idea if Clint Eastwood will ever stop making movies, but if he does, he will leave behind an incredible legacy fitting for one of cinema’s greatest icons.