'Diet Dreams Come True' (1988)

Winfrey has had a long, public battle with her weight. Perhaps the most famous of her weight-loss stories happened in a 1988 episode of her talk show when she famously wore a pair of size 10 Calvin Klein Jeans -- her smallest size in years -- while wheeling a wagon loaded with animal fat to represent the 67 pounds she had lost on a liquid protein diet. Winfrey, who is no longer a size 10, has since called this episode her "biggest, fattest" mistake. She also told Barbara Walters in a 2010 TV special that "I think I did myself a great disservice focusing so much on the external body features ... What I've learned is that overeating for me is about being out of balance and being disconnected and using that as a comfort for the stress."
Charles Bennett / Associated Press
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