Vogue editor Anna Wintour recently revealed in a 60 Minutes interview that she had even "strongly encouraged" Oprah to lose 20 pounds for her 1998 Vogue cover, according to The Insider.

And like a good cover model, Oprah obliged.

"It was a very gentle suggestion," Wintour said. "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 trooper!"