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#15: Elizabeth Taylor (March 4, 1992)
Oprah's first interview in 1988 with Elizabeth Taylor was legendary alright—legendarily bad! Right before the interview Liz announced she wouldn't talk about her famous relationships, and gave short answers to all of Oprah's questions. Oprah later found out Liz was in excruciating back and hip pain at the time.

In their second interview four years later, the queen of Hollywood was finally ready to open up about her marriage (her eighth) to construction worker Larry Fortensky, her close friendship with Michael Jackson, her time in rehab and her tireless work as an AIDS activist.
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