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For the premiere, the show's producers tried rigorously to book Miami Vice's Don Johnson as the first guest, even trying to bribe him with Dom Pérignon and a pair of rhinestone sunglasses.

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Winfrey claims her worst interviewing experience was with Elizabeth Taylor in the show's second season.

Just before the interview, Taylor asked Winfrey not to ask any questions about her relationships.

Winfrey found this to be a challenge considering Taylor had been married seven times.

Taylor returned to the show in 1992, apologized to Winfrey and told her that she was in excruciating back and hip pain at the time.

During the interview, Jackson attempted to dispel many of the rumors surrounding him and told Winfrey he suffered from the skin-pigment disorder known as vitiligo when asked about the change in the color of his skin.