Clint Eastwood has been a prolific filmmaker since his debut in 1955. He has around 200 credits as an actor, director, producer, and even composer, and some of Eastwood’s best movies see him working with the most talented people in Hollywood. With four Academy Awards, a lifetime achievement Oscar, and countless other awards and nominations to his name, it’s safe to say Eastwood’s legacy has been secured for years to come.
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As a director, Eastwood has been able to bring out the best in his actors. His first directing credit was in 1977, and since then, his filmography has included a wide range of projects. From Bronco Billy and Honkytonk Man to Sudden Impact and Gran Torino, he has brought stories featuring an array of fascinating and complex characters to life on-screen. Some of his frequent collaborators include Sondra Locke and Morgan Freeman, but there has been no shortage of standout performances in Eastwood’s movies over the years. The best will stay with viewers long after they’ve finished his movies.
You are watching: 10 Best Performances In Clint Eastwood-Directed Movies
10
Clint Eastwood – Unforgiven (1992)
As William Munny
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What makes Eastwood such a generation-spanning talent is that he’s not only a great director; he’s also an exceptional actor. He’s even directed himself into an Oscar-nominated performance, showcasing the depths of his talent with The Unforgiven. The gritty western took all of Eastwood’s previous experience in the genre and reinvented it for a new decade, so it’s no wonder that it got so much attention at the 65th Academy Awards. And while Eastwood’s movie took home the prizes for Best Picture and Best Director, his performance as William Munny also shines in the 1992 film.
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Eastwood’s performance in The Unforgiven differs from his many previous western roles, where he often plays the gruff hero who saves the day no matter what. William Munny is much more layered, morally conflicted, and has a lot of suppressed emotion as he attempts to navigate his new life away from being an outlaw. Though he lost the leading actor nomination to Al Pacino, this still remains one of the most universally acclaimed and revered roles of his career.
9
Leonardo DiCaprio – J. Edgar (2011)
As J. Edgar Hoover
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J. Edgar follows the life of a very polarizing historical figure, and it rather aptly received polarizing reviews upon its release. But even if parts of Eastwood’s 2011 film miss the mark, Leonardo DiCaprio’s performance as the titular FBI founder doesn’t. DiCaprio masterfully portrays J. Edgar’s life from beginning to end, embodying his paranoia, mannerisms, and even his changing posture as he ages and feels the weight of the world on his shoulders.
DiCaprio is committed to the physicality and voice of his character, and even when the prosthetics don’t quite hold up, he manages to be convincing still.
DiCaprio is committed to the physicality and voice of his character, and even when the prosthetics don’t quite hold up, he manages to be convincing still. The slow pace of the film lends itself to the times in which it’s set, and though lengthy, it’s thorough in its storytelling. This allows DiCaprio to embody Hoover at various stages in his life, and it shows how much he changes over the years. DiCaprio received nominations for a Golden Globe, as well as a Screen Actors Guild Award, for this role.
8
Matt Damon – Invictus (2009)
As Francois Pienaar
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Eastwood showed interest in historical dramas throughout his career, and Invictus is one of his most inspiring stories. It follows Nelson Mandela’s (Morgan Freeman) quest to unite South Africa through the medium of sport — or rugby, to be more specific. As the newly appointed leader of the country, and its first elected black president, Mandela chooses to work with the captain of the South African rugby team, Francois Pienaar (Matt Damon), to create a feeling of togetherness between people of all races throughout the country.
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Damon plays the leader of the Springboks, the team who would eventually win the World Cup in 1995. He was humble and disciplined within his profession, and it’s clear the actor dedicated a lot of time to perfecting his portrayal. His relationship with Mandela provides the emotional grounding of the film, and the two actors work wonderfully together. Damon’s job was not an easy one, with the character he portrayed still alive and well, but he ensured he added his own depth while remaining respectful. He received a well-deserved Oscar nomination for his efforts.
7
Bradley Cooper – American Sniper (2014)
As Chris Kyle
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Another Eastwood movie based on a true story, American Sniper is the harrowing adaptation of an even more harrowing memoir by Chris Kyle, titled American Sniper: The Autobiography of the Most Lethal Sniper in U.S. Military History. Both follow his life as a deployed soldier on four tours of Iraq, and deal with the trauma he experiences upon his return. The brutal action on the battlefield is visceral and resonates with viewers in a deeply disturbing way.
Bradley Cooper’s portrayal of the troubled Chris Kyle is one of his most careful and dedicated roles, as he shows the tragedy of PTSD and survivors’ guilt. His trauma not only affects his day-to-day life, but his family too, and the actor does a powerful job showing his emotional detachment and pent-up stress. The film earned over half a billion dollars at the worldwide box office, and it has been one of Eastwood’s most successful pictures. Cooper was nominated for awards on the circuit, including the Oscar, and his performance is widely regarded as one of his most honest.
6
Ken Watanabe – Letters From Iwo Jima (2006)
As General Kuribayashi
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Part of an ambitious duo of films that are about the same battle but told from different perspectives, Letters From Iwo Jima tells the story of the famed WWII battle from the perspective of the Japanese side. Its companion film, Flags of Our Fathers, tells the story from the American perspective. Unlike many war films, which depict the enemy as faceless oppressors who need to be beaten, Eastwood ensures that the story has more depth and shows the Japanese soldiers’ fears, struggles, and humanity in the face of a ruthless battle.
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Ken Watanabe plays the commander of the Japanese forces stationed on Iwo Jima, and he does so with the utmost class, poise and compassion. He humanizes a character who would otherwise be relegated to a one-dimensional antagonist, as he tries to rally his troops during a time of great adversity. He leads the soldiers just as he leads the film, with bravery and dignity. The film holds 91% on Rotten Tomatoes, which, no doubt, is in some part due to Watanabe’s strong and powerful performance.
5
Meryl Streep – The Bridges of Madison County (1995)
As Francesca Johnson
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The heartbreaking film The Bridges of Madison County sees Meryl Streep as a homemaker and mother, who has spent her life being dutiful and loyal but missed out on passion and adventure. Romance is not often at the very center of Eastwood’s films, but this story, based on Robert James Waller’s novel of the same name, is unapologetically emotional and romantic. Streep and Eastwood have incredible chemistry in their scenes, and seeing slightly older actors in romantic lead roles felt groundbreaking at the time.
In typical Streep fashion, the three-time Oscar winner gives it her all. The longing, the passion, and the burning emotion can be felt in each look and touch the characters share. Her heartbreak and dedication to her responsibilities are all visible through the tears she sheds and the way her voice breaks. The film was a big success and received a lot of recognition during awards season, including another Academy Award nomination for Streep. Her artistry and the connection between the actors can be seen in one specific rain scene, which is filled with so much pain, despite lacking any dialogue.
4
Tim Robbins – Mystic River (2003)
As Dave Boyle
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This dark and troubling crime drama, Mystic River, was an emotional roller coaster, and its story is told in a way that sees tension building slowly but surely. The subject matter is difficult, as it deals with child abuse, murder, and the impact of tragedy on individuals and communities. Mystic River received many nominations for its lead actors — Sean Penn, Marcia Gay Harden, and Tim Robbins — as well as for Eastwood’s directing and Best Picture. Penn and Robbins both won multiple awards, including Oscars in their respective categories.
Though he plays this harrowing role with subtlety, Tim Robbins masterfully conveys how broken his character is inside.
Dave Boyle is the shattered heart of the film, a victim of horrific maltreatment in his childhood, which explains why he is now a deeply troubled adult. Though he plays this harrowing role with subtlety, Tim Robbins masterfully conveys how broken his character is inside. The constant suppression of emotions that’s required to carry on with one’s life after such torment is something Robbins was able to show in his chilling performance.
3
Morgan Freeman – Million Dollar Baby (2004)
As Eddie “Scrap-Iron” Dupris
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As one of the greatest and most prolific actors in cinema, Morgan Freeman has given the world many memorable performances throughout his long and illustrious career. It was quite surprising that his first —and so far, only — Oscar was for Million Dollar Baby at the 2005 ceremony. The award was well-deserved, but it was long overdue. In Freeman’s role as a former boxer and close confidant to Eastwood’s Frankie Dunn, he’s the moral compass of the story, as well as its narrator.
He shares many scenes with Eastwood, who has a more jaded and gruff personality, while Eddie tries to see the good in people and make a positive impact. As a loving mentor figure to Maggie, he can display his caring side, but his inner toughness and strength come out when they have to. In a film that starts out as an underdog sports movie but then sees a much more dramatic turn of events, Freeman serves as the emotional anchor that viewers can depend on when it all gets to be too much.
2
Gene Hackman – Unforgiven (1992)
As Little Bill Daggett
The foil to Eastwood’s conflicted hero, Bill Munny, Gene Hackman plays the brutish and ruthless sheriff who is as corrupt as he is evil in Unforgiven. Further subverting the traditional roles seen in westerns, Hackman goes against the grain and becomes the main antagonist of the movie, despite holding an official position of a law enforcer. He is seen brutally beating, torturing and killing people, all in the name of law and order. His chilling portrayal is layered and not just that of a typical one-dimensional bad guy.
Embracing and highlighting the character’s many flaws but adding context and a particular thought-process to them, Hackman makes his character one of the more interesting and complex villains of the western genre. He doesn’t simply point and shoot, but considers everything to be done for a reason, as part of his plan. His scenes with Eastwood, Freeman and Richard Harris show his calm yet terrifying demeanor in a way that solidifies him as one of the most compelling characters in the film. He received widespread praise for the role, which earned him an Academy Award, among other accolades.
1
Hilary Swank – Million Dollar Baby (2004)
As Maggie Fitzgerald
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Audiences gravitated towards Million Dollar Baby, with its empowering story of an ambitious female boxer who finds success when mentored by a reluctant legend of the sport. Maggie pursues Frankie Dunn, who tells her she is too old, not talented enough, and that he does not want to work with a female boxer. But, through her grit, determination, and physical prowess, she finally manages to get him on side, with a little help from Freeman. What follows is a lot of grueling training, graphic fights, and many moments of both physical and mental strength. Then tragedy strikes.
Hilary Swank had to do it all for this role. From Maggie’s quiet resolve in the face of adversity early in the movie, to the physicality required for her boxing sequences, her performance is an impressive and powerful one. But the depths Swank reaches after the accident happens and her character’s life is changed forever cement her performance as one of the best of her career. She received her second Oscar and swept the board at almost all the other ceremonies. Most importantly, she created a beloved character that lands among Clint Eastwood’s most memorable.
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