After being demoted from anchoring the Baltimore news, Oprah finally found her niche as the co-host of a local morning show called People Are Talking. Then, after hearing that a morning show in Chicago needed a new host, Oprah says she became obsessed with getting the job.
This shot from the original audition tape that got her hired in Chicago is a blast from the past! Needless to say, Oprah got the job. To her surprise, the show was a bit of a disaster at first. But by adding a live audience, Oprah fixed things immediately.
Oprah reveals she and Roger went on a date. "I think it was a date…we went out…we went to a movie…Yeah, I think it was!"
"Roger Ebert told me that syndication would be a good thing for my show," says Oprah. "And there were people who had syndicated his show who were interested in talking to me about it."
"Maybe going national was to help me realize that I have important work," Oprah writes. "Or that this work is important…which is it? And I vacillate between letting this be the most spectacular moment ever and getting goose bumps tomorrow or trying to treat it like an ordinary show. I think I'll end up doing a little bit of both."
The pressure was mounting for Oprah and her small staff to come up with a topic for the big day. The team finally settled on doing a good old fashioned dating show, "How to Marry the Man or Woman of Your Choice." The topic really struck a chord with viewers, making the show a huge success. And, it laid the foundation for what the Oprah Show does best: shows about and with everyday people.
Tina won't be asking Oprah to go on tour anytime soon…but she's still "simply the best"! Read Tina's surprise 20th anniversary message for Oprah.
As a girl, Oprah loved to watch Diana Ross and the Supremes on the Ed Sullivan Show. "I used to stand in front of the bathroom mirror with my brush and pretend I was Diana Ross," Oprah says. "I should have stayed there in front of the mirror with the brush!"
Now Jake is working on a new CD. Sing it, Jake!
The clip was rolled into a show that celebrated some of Oprah's favorite women. That was only the beginning: Mary Tyler Moore had been secretly invited to appear in person! When she walked out on stage, Oprah was absolutely speechless. "I had a happiness headache," she remembers. "My head was pounding after that!"
In her interview with the crown prince of America's "royal family," John shared a memory of his father. "I remember he used to call me Sam to annoy me," John says with a smile. "I'd say, 'My name's not Sam—it's John!' He'd say, 'I'm sorry, Sam.'"
One unanticipated outcome of the John F. Kennedy Jr. interview was a makeover of the Oprah Show set. When the chair left lint all over John's handsome suit, Oprah was mortified and immediately had it recovered in yellow leather—a look that would be used for years.
"I had watched Sidney Poitier win the Academy Award® as a 10-year-old girl. I remember thinking that if he could do that, I wonder what I could do. He has been and is an enormous role model for me."
Oprah felt disappointed with herself after the interview to the point of tears—ugly tears. "I sobbed and cried because I felt I was not good enough for Sidney," she remembers. "I felt like I didn't ask any questions that I should have asked. … I felt like he would never know that I was a smart person with a brain in my head."
Just when Oprah thought she couldn't feel any worse about an interview, the phone rang! It was Sidney calling to tell Oprah he felt the same way.
"It was life-changing," Oprah remembers while speaking to the audience. "I was like, 'Oh my God—"
Mid-sentence, the audience erupts into applause and a puzzled Oprah looks behind her to see what all the cheering is about— a special guest is here to surprise Oprah!
"As an audience, you have seen her vision on your screens. As a friend, I have seen it in action. For 20 years it has remained something to behold. Oprah, congratulations from us all for the past 20 years. May all our best wishes travel with you as your journey continues into the future!"
After taking a moment to wipe her tears, Oprah thanks Sidney and says, "I don't like surprises. I don't know how they kept it from me, because for two months I've been saying, 'No surprises.' But that was worth it!"
Jamie Kennedy, playing the part of an over-the-top Hollywood stylist, transformed one "lucky" viewer from suburban mom to…the dark queen of Goth!
"You can use this look when you pick up your grandkids from kindergarten," Jamie said with a straight face to the bewildered woman. "20 million people are going to see you on Oprah looking like this!"
Right before the interview, Liz asked Oprah not to ask her anything about her relationships. "That's kind of hard to do when you're Elizabeth Taylor and you've been married seven times," Oprah says. Liz's responses were so terse that Oprah couldn't help but tease, "You're so revealing—you just tell everything! I declare, you've got to stop talking so much, Ms. Taylor!"
"To her credit, she later apologized to me," Oprah says. One of the reasons why that interview seemed so painful is because Liz was in a lot of hip pain and back pain at the time.
"I just want to say thank you to everybody who's watched us since you were children. To be able to do this show for 20 years has really been the greatest, biggest, grandest blessing and gift for me and joy of my life. To be able to step into your homes, into your kitchens, into your family rooms, into your bedrooms and feel so embraced is really the greatest honor and privilege. I feel like a part of your lives and for that I will be eternally grateful."