There is only one Clint Eastwood. Of course, there are actors who have gone on to direct and there are directors and producers who occasionally act, but there is no one in film history who has so seamlessly blended these disciplines at such a high level. Given his stature across domains, Eastwood is singular.
In celebration of his recent 89th birthday, we thought it would be fun to discuss Eastwood’s best work. This will include his work in front of and behind the camera, as well as behind the scenes as a producer. What is Clint Eastwood’s very best film?
Early in his career, Eastwood was one of Hollywood’s most famous leading men. He rose to prominence in Sergio Leone‘s “Dollars Trilogy” throughout the 1960s, “A Fistful of Dollars” (1964), “For a Few Dollars More” (1965) and “The Good, the Bad and the Ugly” (1966). “The Man With No Name” was the first of many iconic characters that set Eastwood on a path to superstardom.
He starred in other 1960s Westerns like “Hang ‘Em High” (1968), but it was the 1970s that saw his most iconic character take shape. Eastwood starred in five “Dirty Harry” films, where he played a San Francisco cop doling out his own renegade brand of justice. The role, and Eastwood generally, would go on to define that variation of hyper masculinity on the big screen.
The 1970s also marked the beginning of Eastwood’s work as a director. He made his directorial debut in 1971 with “Play Misty for Me.” The film was a critical and financial hit and gave Eastwood the runway he used to become one of Hollywood’s most prolific directors. Throughout the 1970s, he would direct himself in films like “High Plains Drifter” (1973) and “The Outlaw Josey Wales” (1976).
Eastwood would continue to direct into the 1980s with movies like “Heartbreak Ridge” (1986) and “Bird” (1988), with each garnering attention from the Academy. “Bird,” the biographical film about the life of Charlie Parker, won the Academy Award for Best Sound in a sign of what was to come for Eastwood.
In 1992, Eastwood directed “Unforgiven,” which tells the story of an aging outlaw who takes on one more job after retiring to a life of farming. Many consider the movie a bona fide masterpiece. The film received nine Oscar nominations and won four, including Best Picture and Best Director for Eastwood. This remains his most awarded film, but he has several others that came close.
The rest of the 1990s include films like “The Rookie” (1990), “The Bridges of Madison County” (1995), “Absolute Power” (1997) and “True Crime” (1999).
In 2003, Eastwood directed “Mystic River,” a murder-mystery that follows a tragic event, bringing a group of childhood friends back together under horrible circumstances. Eastwood was again nominated for Best Picture and Best Director, but the film only scored victories in the acting categories for Sean Penn and Tim Robbins.
The very next year, Eastwood produced, directed and starred in “Million Dollar Baby” (2004). The boxing story wanders between family drama and the difficulty of decisions made with conviction. The film would go on to win four Oscars including Best Picture and Best Actress for Hilary Swank. It is also one of the more commercially successful efforts of Eastwood’s illustrious career, grossing $217M at the global box office.
But no discussion of Eastwood’s commercial appeal would be complete without “American Sniper” (2014). The film became a surprise hit and went on to gross nearly $550M. The film earned six Oscar nominations, including Best Picture and Best Actor for Bradley Cooper.
Late in his career, Eastwood has become quite productive with films like “Letters From Iwo Jima” (2006), “Changeling” (2008), “Invictus” (2009) and “Sully” (2016) all generating at least one Oscar nomination. In a career as long and as storied as Eastwood’s, there are always more notable films, but we want to hear from you!