Clint Eastwood Turns 96: 5 Must-Watch Movies From Hollywood Icon's Remarkable Career Amid Retirement News

Released in 1976, The Outlaw Josey Wales features Clint Eastwood both behind and in front of the camera. The western follows Josey Wales, a Missouri farmer whose life is shattered when Union militants kill his family during the Civil War. Driven by revenge, he joins Confederate fighters. But, after his fellow soldiers are killed following their surrender, Wales becomes a fugitive, battling enemies while seeking justice.

Dirty Harry (1971) gave Clint Eastwood one of the most memorable roles of his career. He stars as Inspector Harry Callahan, a fearless San Francisco detective known for his unconventional methods and refusal to play by the book. Armed with his famous .44 Magnum, Callahan pursues a dangerous serial killer, doing whatever he believes is necessary to bring the criminal to justice. Notably, Dirty Harry has four sequels, including Magnum Force, The Enforcer, Sudden Impact, and The Dead Pool.

Released in 1966 and directed by Sergio Leone, The Good, the Bad and the Ugly stars Clint Eastwood as Blondie, the mysterious gunslinger often called the Man with No Name. Set during the Civil War era, the film follows three rivals searching for hidden gold. Eastwood’s character forms a fragile partnership with one of his competitors, Tuco, as they race across the West, each hoping to claim the treasure first.

In Million Dollar Baby (2004), Clint Eastwood plays Frankie Dunn, a veteran boxing trainer carrying years of regret and emotional baggage. His life changes when he agrees to mentor Maggie Fitzgerald, an ambitious 31-year-old aspiring boxer portrayed by Hilary Swank. Beyond starring in the film, Eastwood also directed, produced, and composed its score, making it one of the most personal projects of his career.

In Unforgiven (1992), Clint Eastwood portrays William Munny, a former outlaw who left behind his violent past after falling in love and starting a family. Years later, following his wife's death, Munny struggles to support his two children. Facing financial hardship, he reluctantly accepts a bounty-hunting job, forcing him to confront the life he worked so hard to leave behind.