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MacLeod's first movie appearance was a small, uncredited role in The True Story of Lynn Stuart in 1958.
Soon thereafter, he landed a credited role in I Want to Live !, a 1958 prison drama starring Susan Hayward.
He was soon noticed by Blake Edwards, who in 1958 cast him as a neurotic harried navy yeoman in Operation Petticoat with Cary Grant and Tony Curtis.
Operation Petticoat proved to be a breakout role for MacLeod, and he was soon cast in another Edwards comedy, High Time, with Bing Crosby.

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