Even though he has a career in cinema spanning over half a century, Clint Eastwood has shown no signs of slowing down at age 86. Sully, his 35th film as a director, is opening this weekend to positive word of mouth. In a career as expansive as any filmmaker today, Eastwood’s directorial track record is full of peaks and valleys. From gritty westerns to historical dramas, each film in his canon has something worthwhile. With that said, a few of his films have helped to define his legacy. Here are the five films that stand head and shoulders above the rest as his most important and defining directing efforts. At the risk of sounding redundant, Unforgiven was left off this list.
Play Misty for Me (1971)
For an actor who had already been defined as the definition of male machismo as The Man With No Name, Eastwood’s directorial debut was a surprising departure. His role as a stalked radio DJ is a subversive deconstruction of his established tough guy image. Made under the tutelage of his mentor/collaborator Don Siegel, Eastwood’s character is a rarity for him because he spends much of the film in a lose-lose situation. With a nail-biting climax, Eastwood made his presence known as a director who could produce tension and suspense out of a simple premise.
The Outlaw Josey Wales (1976)
At the core of many of Eastwood’s westerns is the nature of violence. Nowhere is this more fascinatingly explored than in The Outlaw Josey Wales. A post-Civil War revenge story, the film centers on a revenge driven farmer who joins up with Confederate renegades. While it’s a revenge film, it possesses an interesting dichotomy given that it’s also a call for pacifism. Equally revisionist and with outstanding cinematography by Bruce Surtees, The Outlaw Josey Wales is a benchmark for someone so tied to the hip of the genre.
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Bird (1988)
Eastwood’s recent films centering on historical figures (J. Edgar, American Sniper) have felt emotionally hollow. Bird is an exception, a mostly factual tribute to both the titular musician and the jazz genre. The back and forth narrative does a brilliant job in showing the life of tortured artist Charlie Parker. Masterfully portrayed by Forrest Whitaker, Parker’s world was dour and dark and Eastwood certainly taps into that aesthetic. It’s a touching movie that’s made with equal parts anger, enthusiasm and sadness.
Mystic River (2003)
Mystic River is a film that took multiple viewings for me to appreciate its value. Upon first view, I found the film to be rather cold and off-putting. Its dark subject matter, visceral lead performances, and methodical pace muddled the messages Eastwood wanted to convey. When I sat down to watch it once again for this, I realized that absence does make the heart grow fonder. It’s a film about how murder can bring old acquaintances closer and how the past affects the actions of some in the present. More than that, it combines a family drama with an involving detective story. Through this investigation, we delve into the minds of the three main characters and learn that not all wounds heal with the passage of time.
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Letters From Iwo Jima (2006)
A companion piece to Flags of our Fathers, Letters from Iwo Jima depicts the same battle from the Japanese perspective. The Japanese aren’t hidden in the shadows like most war epics, instead they’re well-developed protagonists caught in hell on earth. It’s a non-jingoistic take on war, with a sense of imposing dread before every battle scene. Unlike American Sniper, the film appears to regret the existence of war rather than choosing to glorify it. Eastwood presents the conflict as subjective from a completely impartial perspective. After The Outlaw Josey Wales, this is my favorite of Eastwood’s filmography.
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