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Oprah Winfrey

When it comes to weight-loss tabloid fodder, Oprah, 57, reigns supreme. Her weight has fluctuated often and drastically, and it’s always been "breaking news." The yo-yoing is partly due to a thyroid condition, which she said she had leaned on as an excuse to eat whatever she wanted in the past.

In the early 2000s, she trimmed down to a fit 160 and thought she had finally conquered her weight issues. But in 2008, she opened up that she had hit 200 pounds—again. In 2010, she announced on her show that she would never diet again.

Next: Drew Carey