Oprah Calls Her Biggest Moment a Big Mistake

There have been many memorable moments in the 20 years Oprah Winfrey has been on the air, but the megastar says the biggest one was a huge mistake.

In 1988, Winfrey lost 67 pounds in four months by eating virtually nothing. At the end of her liquid diet, she appeared on her show in a pair of size 10 Calvin Klein jeans pulling a wagon full of fat, representing the 67 pounds. But the minute after the show was over, Winfrey said she started putting the weight back on.

"It's an iconic moment because it was an iconic mistake," Winfrey said in an interview with "Good Morning America." "It was a great, great, great big lesson … I felt so, like, this will never, I will never, ever have a weight issue again."

A week after the show, Winfrey said she put on 10 pounds and couldn't bring herself to attend a party at the home of her friend, Don Johnson.

"I was too embarrassed to go to the party," Winfrey said. "Everybody's going to see me on TV, but I can't go out to a party because everybody's going to see that I gained the weight back."

Winfrey reveals the rest of her top 20 moments in her 20th anniversary DVD which also includes her favorite guests, celebrities and people who have touched her life in her two decades on the air. The DVD contains footage of Winfrey when she was starting out in Baltimore, a personal tour of her home and behind-the-scene footage from the show.

Changing America

Winfrey was 19 when she became the youngest person and first African-American woman to anchor the news in Nashville, Tenn. In 1976, at the age of 22, she became a newscaster at WJZ-TV in Baltimore. Today, Winfrey is one of the most powerful women in the world, with the annual revenue of her businesses estimated at $275 million.

"The greatest running thing for me, aside from you are not alone and you must take responsibility for your own life, is that everybody wants to be validated," Winfrey said. "In every single interview for the 17 hours of that tape (the anniversary DVD), the theme for every single person, regardless of who it is or what the subject is, is 'Do you hear me? And did what I have to say mean anything to you?'"

Through the years, Winfrey has interviewed everyone from the flashiest celebrities, to the everyman and everywoman of Any Town, USA.

In 1987, Winfrey interviewed residents from an all-white county in Georgia, and a virulent explosion of racism ensued with the "n" word used over and over again to Winfrey. She said that was enough.

"I felt in the early years of my career that it was necessary for me as an African-American to challenge anybody who was saying anything about black people," Winfrey said. "And then in the middle of one of those shows -- this is after Forsyth County -- I realized I was not doing myself nor anyone else any good."

Winfrey said she came to the realization when friends of racist guests on her show were cheering the racists on, it was because they were on television.

"Then I thought, well, this is crazy," Winfrey said. "So I decided not to do it anymore."

Oprah's Secrets

It's hard to ask Winfrey a question she has not asked before, but "GMA" gave it a try.

Winfrey was at a loss for who she would kiss other than Steadman Graham, her boyfriend of 18 years, but would "think about it." When asked who Winfrey would marry if she was a man, Winfrey said Selma Hayak.

"I went to interview her (Hayak) for my magazine and I thought it was going to be an hour, two hours," Winfrey said. "Four hours later we were still talking."

Winfrey revealed her secrets to getting through tough days.

"There have been some times, even here, you know, at work, if there's one more thing, I'm going to rip my clothes off and go screaming down the hall," Winfrey said. "When that happens, I go into my closet and I close the door, turn off the lights, and I sit on the floor and breathe until I can calm myself down and go back to something that is real, that is not, you know, the next person standing outside the door waiting to have a meeting."

But even after 20 years, Winfrey said she still has passion for her job.

"Now I feel like we kicked into another gear," Winfrey said. "I feel like, literally, something happened to me when I turned 50. I expected that it was going to be good because Maya Angelou had told me that the 50s are everything you've been meaning to be. That's when it all comes together and you will, you know, finish this decade and say, yeah, that's what it was meant to be."

Tune in to "Good Morning America" on Friday to hear about who she would kiss other than Steadman, her thoughts on Tom Cruise and more on the 20 years of her show.