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Oprah Winfrey
In 2009, Oprah Winfrey singled out a 1988 sit-down with Taylor as her worst interview in 20 years. "It's still painful to watch," the talk show host said. "For many reasonsincluding my bad hair." Still, when the two crossed paths at the 2002 Carousel of Hope gala, it appeared as though they had smoothed things over.