Clint Eastwood Holds An Oscars Record That Still Hasn't Been Broken

When Clint Eastwood became a familiar face to U.S. television viewers via his portrayal of ramrod Rowdy Yates in the CBS Western drama "Rawhide," no one save for maybe his mother saw his handsome mug on their television screen and said, "This man is going to be a transformational figure in motion pictures." No one could've predicted that he'd fly to Spain during his 1964 hiatus from "Rawhide" and make a one-of-a-kind Western with an upstart Italian director named Sergio Leone, thus launching an entire subgenre that would turn him into an international movie star. They certainly couldn't have guessed that he'd also redefine the cop film as a due-process-flouting hardass named Harry Callahan. And then to become a celebrated filmmaker in his own right? Crazy talk.

Clint Eastwood has defied expectations and categorization. At the moment that he was riding high on Westerns and his Dirty Harry persona, he turned around and made his directorial debut with "Play Misty for Me," a deeply unnerving thriller where he stars as a caddish Bay Area radio DJ who attracts potentially fatal attention from a devoted listener (the great Jessica Walter). From that point forward, critics and audiences had to take him seriously as an artist — though he didn't always make it easy with lunkheaded movies like "The Gauntlet," "Every Which Way But Loose" and "Any Which Way You Can."

The Academy of Motion Picture Arts and Sciences was hesitant to embrace Eastwood, but he finally forced the issue with "Unforgiven," a revisionist Western that earned rave reviews and grossed $101 million at the U.S. box office. He won Best Picture and Best Director at the 1993 ceremony, which felt like a coronation. But Eastwood wasn't done. And a decade later, he'd set an Oscar record that stands to this day.

Were it not for Peter Jackson's "The Lord of the Rings: The Return of the King" hitting its Oscar victory lap in 2004, Eastwood probably would've won Best Picture and Best Director for his adaptation of Dennis Lehane's neo-noir novel "Mystic River," for which he'd received some of the best reviews of his career. The timing wasn't right that year, but he wound up getting a favorable Oscar draw the next year when he made the deeply sad "Million Dollar Baby."

The boxing melodrama about a talented woman boxer (Hilary Swank) whose career and life are derailed by a cruel twist of fate faced stiff competition from Martin Scorsese's "The Aviator," but came out on top at the 2005 Academy Awards. The film won four Oscars, but its most notable triumph was Eastwood's second Best Director trophy. At the age of 74, Eastwood became the oldest helmer to win the award, placing himself six years ahead of previous record-holder Roman Polanski, who was 68 when he won in 2003 for "The Pianist."

With masters like Steven Spielberg (78), Martin Scorsese (82), and Francis Ford Coppola (85) still active, Eastwood's record isn't necessarily safe. Then again, if Eastwood can make a film as good as "Juror #2" at the age of 94, he's as much a threat to break that record as any of his peers.