Oprah auditions for her new job

The magic all began back in 1973. Only 19 at the time, Oprah got her television start covering local news in Nashville. She then moved on to Baltimore to become an anchorwoman for the evening news. From the beginning, Oprah says she preferred telling people's stories to reporting straight-up news.

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.
Roger Ebert plants the seed for syndication

Although Oprah's never told this story publicly, she says film critic Roger Ebert played an important role in syndicating her show.

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."
The first 'Oprah Show'

Less than two years after Oprah debuted on A.M. Chicago, The Oprah Winfrey Show was born. At midnight on September 8, 1986—exactly eight hours before her very first national television show—Oprah wrote an auspicious journal entry. "I keep wondering how my life will change, if it will change, and what all this means. Why have I been so blessed?"

"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.
'Oprah Show' footage from the archives"

Women still talk about the 1989 show, "Alaskan Men." Oprah and her staff loaded up a plane with handsome, single Alaskan men—all looking for wives. And when they arrived at the airport in Chicago, it was as if the Beatles had landed! Eager bachelorettes stormed the airport to get first dibs on the Alaskan men. "It was fun…it was thrilling!" says Oprah.
Tina Turner

While on tour, Tina Turner invited Oprah to join her on stage for a taste of rock-stardom. Before their brief performance, Oprah was so nervous, her knees were literally knocking together! She says the unnerving experience taught her to seize the moment.

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.
Oprah's supreme makeover

Looking back over the years, Oprah says there have been a handful of moments that simply make her cringe! Topping that list of embarrassing moments is the time Oprah dressed up as one of her biggest heroes, Diana Ross.

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!"
The car giveaway

It doesn't get any bigger than this! According to TV Guide , this moment made television history. For the spectacular launch of the show's 19th season , nearly 300 deserving audience members received brand-new cars. Oprah was on pins and needles before the big surprise. "It was a secret so big, I did not even tell Stedman," she says. "I couldn't sleep the whole week before, I was so excited!"
Stevie Wonder surprises his biggest fan

One of Stevie Wonder's biggest fans got the surprise of a lifetime during the Oprah Show's Wildest Dreams season. Jake Simpson, the reigning Star Search Grand Champion, came on the show expecting to talk about his big win. Little did he know his music idol was hiding behind a curtain wall on the set. As Jake began to perform, the curtains parted to reveal Stevie, leaving Jake speechless—but not breathless. Sharing the spotlight, the two sang "Isn't She Lovely" together, fulfilling Jake's once-in-a-lifetime dream.

Now Jake is working on a new CD. Sing it, Jake!
Mary Tyler Moore surprises Oprah

As a young, aspiring newswoman in the '70s, Oprah wanted to be Mary Tyler Moore. To help Oprah live out that fantasy just a little bit, her producers recreated the opening to The Mary Tyler Moore Show replacing Miss Mary with Oprah!

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!"
Oprah wheels out the 'fat wagon'

The show Oprah considers her "biggest, fattest" mistake is also the highest-ranking episode in 20 years! To represent her recent 67-pound weight loss, Oprah wheeled a wagon of fat onto the stage. "I had literally starved myself for four months—not a morsel of food—to get into that pair of size 10 Calvin Klein jeans," Oprah remembers. "Two hours after that show, I started eating to celebrate—of course, within two days those jeans no longer fit!"
Oprah interviews John F. Kennedy Jr.

Oprah says she will always remember John F. Kennedy Jr. for his humility and graciousness. "His mother raised him right!" she says.

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.
Oprah's interview with Sidney Poitier

Oprah says that she never had a show make her break down crying afterward—until she interviewed Sidney Poitier.

"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!
Sidney Poitier surprises Oprah.

Sidney Poitier is here and has a special message to celebrate Oprah's 20 years on air! "In these last 20 years, America's media industry would have been considerably less vibrant without the genius of Oprah Winfrey," he reads from his letter.

"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!"
A 'lucky' viewer gets a makeover from prankster Jamie Kennedy

A few years ago, we did something we'd never done before—we gave viewers awful makeovers! Prankster Jamie Kennedy helped us set up the gag—what happened next was one of our best practical jokes ever….

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!"

Oprah interviews Elizabeth Taylor

Looking back over 20 years, there's only one interview that Oprah calls her worst: Elizabeth Taylor. "It's still painful to watch," she says, "For many reasons—including my bad hair."

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.
Oprah thanks her viewers.

A message of appreciation from Oprah:

"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."