Anna Wintour Dishes on Telling Oprah Winfrey to Lose 20 Pounds for 1998 Vogue Cover

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Notorious Vogue editor-in-chief Anna Wintour finally admitted to requesting Oprah to lose weight for her 1998 Vogue cover shoot.

Telling the talk show host to drop 20 pounds for her cover, Wintour revealed on 60 Minutes, “It was a very gentle suggestion. I went to Chicago to visit Oprah, and I suggested that it might be an idea that she lose a little bit of weight.”

Oprah appeared on the October 1998 cover with the headline: “Oprah! A Major Movie, An Amazing Makeover.”

“She was a trooper,” Wintour added. “She totally welcomed the idea, and she went on a very stringent diet. And it was one of our most successful covers ever.”