15. Oprah Winfrey's Head on Anne Margaret's Body

Year: 1989

Before we actually had Photoshop, pictures had to be manipulated the old-fashioned way. And the classic, first example of this in the media world was Oprah Winfrey on the cover of a 1989 TV Guide. Without getting permission from either woman, the magazine grafted the head of Oprah onto the body of '60s star Anne Margaret. Uproarius? Not entirely. But strange? Certainly.

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