1. Unforgiven (1992, actor and director)
Eastwood held onto the script for this David Webb Peoples (Blade Runner) revisionist Western for years until he had the wisdom and seriousness to present it in the best light possible. Well worth the wait; As the tale of an elderly reformed gunslinger (Eastwood) coming out of retirement, this is a moving meditation on sin, fate, and redemption. Unforgiven projects a powerful anti-violence message without preaching by challenging the myths of good people and bad people. The actor-director's final foray into the Western genre garnered Oscars for Best Picture, Best Director, Best Editing (Joel Cox), and Best Supporting Actor (for Gene Hackman's astute work as ruthless sheriff Little Bill Daggett). It is indisputably Eastwood's masterpiece.
2. Mystic River (2003, director)
Here we see something completely unexpected from Eastwood: a devastating contemporary crime story set in Boston (adapted from Denis Lehane's novel) that deals with complex themes of pain, anger, and trauma. Sean Penn and Tim Robbins justifiably won best actor and best supporting Actor Oscars the first time a film has won both since 1960's Ben-Hur - as childhood friends torn apart by murder. Mystic River also highlights two of the most fully realized female characters in Eastwood's work, as the wives of Penn and Robbins. Although the director does not appear in the film, he arranged the moving score. He enjoys the special performance of his co-star on The Good, the Bad, and the Ugly, Eli Wallach as a liquor store owner.
3. Million Dollar Baby (2004, actor and director)
This movie was a success for many reasons. For starters, Hilary Swank's transformative commitment to the role of an underrated boxer; she put on nearly 20 pounds of muscle for the performance and dove right into the skin of her character, earning her her second Best Actress Oscar (following 1999's Boys Don't Cry). And then there's Morgan Freeman, who reunited with his director on Unforgiven and won a best supporting actor Oscar for the role of a former boxer who loses sight in one eye, but not the ability to see inside. souls of people Lastly, we have Eastwood, who pours all of his life experience into the portrayal of a tough-love coach, earning him a best actor nomination. Eastwood also earned best picture and best director nods for gracefully guiding a story that takes a sharp left turn midway through and turns into something far more poignant than the female Rocky he first appeared to be.
4. The Outlaw Josey Wales (1976, actor and director)
Premiering on the night of the bicentennial, this cowboy flick pays tribute to the spirit of America's rugged individualism. It's a simple story on its face: a Missouri farmer seeks revenge against the renegade soldiers who murdered his wife and son after the Civil War. But in the hands of Eastwood—who took the directorial reins from co-writer Philip Kaufman (The Right Stuff) early in production—it becomes a rousing picaresque adventure. The high-caliber cast includes Chief Dan George (Little Big Man) and Eastwood's real-life romantic interest, Sondra Locke.
5. The Good, the Bad, and the Ugly (1966, actor)
Almost everything about director Sergio Leone's spaghetti Westerns is super-great: the wordy title, the running time (nearly three hours), Ennio Morricone's instantly evocative score, the jaw-dropping panoramas, and the extreme close-ups. All of this makes Eastwood's mild-mannered performance the perfect foil as the more moral member of a trio of bounty hunters searching for buried gold during the Civil War. Donning his iconic poncho and cigarette, his easy-going charisma ultimately turns out to be as combustible as the explosives he uses to blow up a bridge in the film's most spectacular scenery.
