Anna Wintour told Oprah to lose 20 pounds

Oprah Winfrey graced the cover of Vogue magazine in 1998 looking like a lean, mean, talk-show-hosting machine! What you didn't know, though, was that Oprah was a little chunky just before the shoot, and was told by the mag's editor Anna Wintour to drop 20 pounds.

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. I said simply that you might feel more comfortable. She was a trouper! She totally welcomed the idea, and she went on a very stringent diet. It was one of our most successful covers ever.

11 years later, Oprah has admittedly ballooned back up to over 200 pounds. Maybe it's time Anna tells her to drop some poundage again, and reward her with a re-make of her Vogue cover? Talk about incentive.