Rather interviewed Hillary Clinton several times throughout his career: in 1993, for example, he talked to the First Lady about the healthcare program she and President Clinton were working to pass through Congress. In May 1999, he sat with with her in another exclusive interview, her first wide-ranging one in almost a year. As producer Dana Roberson remembers, there was a lot of competition to get the interview as all the networks were wooing the First Lady at a time when many wondered if she would run for the U.S. Senate.

This interview also illustrates some of Rather's interviewing skills, as he was able to ease the tension and make the First Lady comfortable.