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Paulll

The first actor/actress that comes to mind..

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Charles Laughton

Next:  another leading man without typical leading man good-looks

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Kirk Douglas in "Paths of Glory" (1957) = banned in France due to depiction of the French Army

Next: a dictator

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Claudio Spadaro in TEA WITH MUSSOLINI (1999)

Next: a singer turned actor/actress

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Piper Laurie (in "Tim")

Next: another person who played the older half of a May December romance

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Dick Van Dyke in The Art of Love (1965)

Next:  another directed by Norman Jewison

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