Oprah and Al Gore

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Season 15: "Season Premiere: Vice President Al Gore"
By the time Oprah's season premiere aired on September 11, 2000, the race between Vice President Al Gore and Texas Governor George W. Bush was the closest presidential race in 20 years.

Vice President Gore's interview was also the first time Oprah had ever interviewed a politician running for office. "I've stayed away from politicians really for one main reason: I never felt I could have a real honest conversation with them. To me, there seems to be this wall that exists between the people and the authentic part of the candidate," she said. "I thought, 'Well, okay, 15 years. I need to try to penetrate that wall.'"

The week after Vice President Gore's appearance, Oprah sat down with George W. Bush. "What we hope is that at the end of these two shows, you'll be able to answer for yourself some of the bigger questions, like 'Who do you trust?'" she said.