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Split image of an older male celebrity in his 20s wearing a sweater and now in a suit at a red carpet event, showing older celebs.

Clint Eastwood operated in a league of his own and carried a unique charm—something that came through most vividly during his encounter with the late firebrand journalist Barbara Walters. Known for dismantling Hollywood heavyweights and world leaders alike, Walters likely thought she’d flay him just the same.

But that’s not how it played out. The Dirty Harry actor flipped the script, disarming her with quiet confidence until she was the one blushing and stumbling over her words. Born in California in May 1930, Eastwood lived through the Great Depression, which began in 1929 and lasted until 1939, and later served in the Korean War from 1950 to 1953.

He began his acting career after his military service, landing the role of Rowdy Yates in Rawhide (1959–1965). His twenties coincided with his war years, and after returning home, he married model Maggie Johnson. A year later, Eastwood briefly became a model himself.

Perhaps due to a habit formed during his time in uniform, every image of young Eastwood shows him immaculately clean-shaven, with a classic short back and sides—a timeless look that only added to his mystique.

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