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Watch: Oprah Winfrey Jokingly Reveals One “Bad” Career Mistake

When The Oprah Winfrey Show premiered on Sept. 8, 1986, the host had no idea if it would even last a month, let alone 25 years and change the entire media landscape in the process.

“I knew my life was about to change,” Oprah Winfrey reflected in 2025 on her Oprah Daily site. “What I couldn’t have imagined was the force for good the show would become—the impact it would have on me, on my team (the best team in television), and on the millions of lives we touched.”

She had sensed, as a newswoman anchoring AM Chicago who would get reprimanded for empathizing too much with the people she reported on, that she was meant to do more with her voice.

“I never felt comfortable in my own skin,” Winfrey recalled to TIME in 2017. “I always felt like I had a pretend voice when I went on the air.”

So, when Oprah debuted with the episode “How to Marry the Man/Woman of Your Choice,” her authenticity radiated through the screen.

“The talk show really freed me,” she admitted. “I went only from what was in my heart…It was like coming home.”

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Oprah Through the Years

Betting on herself was the first step. And as her eponymous cable network, book club, magazine and everything else stamped with a golden “O” imply, that’s what the 72-year-old billionaire has been doing ever since.

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Even saying goodbye in 2011 to the show that started it all was more of a bridge to her next favorite thing than an ending.

“It holds a space with me that is me and will forever be me until my last breath and beyond,” Winfrey told Entertainment Weekly five years later. “But ‘miss’ is not the word. I cherish everything it represented.”

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And while TV has certainly changed, Winfrey’s interest in moving the needle has not, hence her recent decision to expand The Oprah Podcast to twice-weekly episodes that, since they’re also on YouTube, aren’t all that unlike watching a syndicated talk show.

“I have observed so much from human behavior, how to live a life that is actually meaningful, purposeful, and fills you with a sense of contentment,” she said in an August interview with LinkedIn Editor in Chief Dan Roth. “Being able to do that podcast is an opportunity, at this point, to offer what I’ve learned, what I’ve grown into, a sense of knowingness, a sense of wisdom—in the wisdom seat at 72—to other people.”

So, while Winfrey just can’t stop, won’t stop delving into what makes her guests tick, read on to learn all sorts of new fascinating things about the tastemaker herself:

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1. Oprah was born on January 29, 1954 in Kosciusko, Mississippi to unmarried teen mother Vernita Lee.

Afro American Newspapers/Gado/Getty Images

2. Her first name is actually spelled Orpah on her birth certificate after a biblical figure in the Book of Ruth, but people mispronounced it and Oprah stuck.

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3. She grew up believing Vernon Winfrey was her biological father, however, in 2003, Mississippi farmer and World War II vet Noah Robinson Sr. came forward with a claim that he was her actual father. She refused a paternity test.

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4. Oprah spent the first six years of her life living with her grandmother Hattie Mae Lee, who was so poor that the future media mogul often wore dresses made of potato sack. The unconventional clothing earned her the nickname “Sack Girl” among the local children.

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5. According to Oprah, she used to endure some harrowing physical punishments at the hand of Hattie Mae. “I went to a well to get some water and carry it in a bucket. And I was playing in the water with my fingers, and my grandmother had seen me out the window and she didn’t like it,” she told David Letterman in 2012. “She whipped me so badly that I had welts on my back and the welts would bleed. And then when I put on my Sunday dress, I was bleeding from the welts. And then she was very upset with me because I got blood on the dress. So then I got another whipping for getting blood on the dress.”

Paul Drinkwater/NBCU Photo Bank/NBCUniversal via Getty Images via Getty Images

6. Hattie Mae also taught Oprah how to read by the age of three and would take her to church, where she earned the nickname “The Preacher” for her ability to recite Bible verses.

Jim Smeal/Ron Galella Collection via Getty Images

7. When she was six, she moved to Milwaukee, Wisconsin to live with her mother, who had given birth to another daughter, Patricia, in the six years that Oprah was living with her grandma. Patricia would later die of causes related to a cocaine addiction at the age of 43.

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8. By 1962, unable to care for her two daughters, Vernita would send Oprah to live with her father Vernon in Nashville, Tennessee. While she was away, Vernita would give birth to another daughter (who she placed for adoption and was later named, coincidentally, Patricia) and a son, Jeffrey. Oprah wouldn’t even learn of Patricia’s existence until 2010. Jeffrey, however, died of AIDS-related causes in 1989.

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9. As she revealed on her talk show in 1986, Oprah was molested by a 19-year-old cousin when she was only nine years old. For years after that, she was also assaulted by an uncle and a family friend. When she opened up about the alleged abuse at the age of 24 to family members, they reportedly did not believe her.

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10. She became pregnant at 14 and prematurely gave birth to a baby boy, who died shortly after being born. The world learned of Oprah’s secret pregnancy in 1990 when a family member sold the story to the National Enquirer. While Oprah didn’t name which family member betrayed her when writing about the experience for O, The Oprah Magazine‘s February 2007 issue, the Associated Press reported it was her deceased half-sister Patricia who, as Oprah wrote, “sat in a room, told them the story of my hidden shame and left their offices $19,000 richer.”

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11. While in high school, Oprah returned to Nashville for good to live with Vernon, where education at East Nashville High School became a priority. There, she was voted Most Popular Girl and joined the speech team, which helped her secure a full scholarship to Tennessee State University.

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12. Her first job as a teenager was working at a grocery store, where she was, ironically, forbidden from speaking with customers.

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13. In 1971, after Oprah won Nashville’s Miss Fire Prevention contest, the pageant’s sponsor, radio station WVOL, offered her a job reading the afternoon headlines on air.

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14. In 1972, she won Miss Black Tennessee and went on to compete in Miss Black America.

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15. At just 19, she became both the youngest news anchor and first Black female anchor for Nashville’s WLAC-TV, leaving TSU, where she was studying communications, to do so.

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16. After an eight-year stint co-hosting a local morning show in Baltimore, Maryland, she relocated to Chicago to take over WLS-TV’s low-rated half-hour morning show, AM Chicago, in 1983. Her first episode aired on January 2, 1984 and, within months, the show went from last place to besting Donahue as the highest-rated talk show in Chicago.

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17. When Oprah received the offer from King World to take her show into national syndication, it was famed movie critic Roger Ebert who convinced her it would be foolish to say no.While on their first of two dates in the mid-‘80s, he grabbed a napkin at the restaurant where they were enjoying dinner and started “jotting down some numbers,” according to a 2005 post on Oprah.com. By his prediction, she would make 40 times what he was making for At the Movies. “He slid the napkin across the table to show Oprah the final tally and she said, ‘Deal done!'” The Oprah Winfrey Show began broadcasting nationally on September 8, 1986.

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18. Before The Oprah Winfrey Show went national, Oprah was already a household name thanks to her work in Steven Spielberg‘s 1985 adaptation of The Color Purple. For her turn as Sofia in the film, Oprah was nominated for Best Supporting Actress at the 1986 Academy Awards.

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19. In 1986, Oprah launched her multimedia production company Harpo Inc. The name is both her name spelled backwards and the name of her The Color Purple character’s husband.

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20. For the first national episode of her show, Oprah wanted Don Johnson, star of Miami Vice (then the biggest show on TV) as her first guest, even going so far as to send him a very expensive pair of rhinestone sunglasses to try and persuade him. But he wasn’t feeling it.Rather than find a back-up star, Oprah had the genius idea to make her show not just about celebrities, but about everyday people, also. “So what we came up with was a show called ‘How to Marry the Man of Your Choice,'” she explained years later.Johnson would eventually appear on her show, during the premiere episode of the final season in 2010. And he made sure to return the glasses. “I know it has taken me about 24 years to get these back to you,” he told her.

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21. In one of Oprah’s most memorable early episodes, after a highly-publicized diet, she arrived on stage in 1988 pulling a wagon full of 67 pounds of animal fat to illustrate exactly how much weight she’d lost.In 2016, she told Entertainment Tonight that the unforgettable moment was also one of her biggest regrets. “Big, big, big, big, big, big, big mistake!” she told the outlet. “When I look at that show, I think it was one of the biggest ego trips of my life.”

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22. In 1993, Oprah sat down with Michael Jackson for an interview that broadcast live from his Neverland Ranch. It was the entertainer’s first interview in 14 years and, as such, it really brought in the viewers.Taking place before any allegations of sexual abuse had been made, the interview became the fourth most-watched event in American TV history and the most watched interview ever, with an audience of 90 million worldwide.

Vera Anderson/WireImage

23. While interviewing four mothers with past drug problems alongside Washington Post reporter Patrice Gaines on her show in 1995, Oprah admitted on-air that she’d smoked crack cocaine in her 20s.”Let me say this, and this is probably one of the hardest things I’ve ever said,” she said, her voice cracking. “But I was involved with a man in my 20s who introduced me to the same drug that you’ve been talking about and, like Patrice, I always felt that the drug itself is not the problem but that I was addicted to the man. I can’t think of anything I wouldn’t have done for that man.”

Alberto E. Rodriguez/Getty Images for Disney

24. In 1996, Oprah launched the Oprah’s Book Club segment on her show. Proving how much power her endorsement carried, each new book she announced as the latest in her club would go on to become a best-seller and the term “The Oprah Effect” was coined.

Kevork Djansezian/NBCU Photo Bank/NBCUniversal via Getty Images via Getty Images

25. When official book club selection A Million Little Pieces was proven to be a fabrication by author James Frey in 2006, Oprah brought the author and his publisher Nan Talese onto her show to publicly chastise them.She told James that by fabricating part of his purported true story of addiction and recover, he’d “betrayed millions of readers,” before forcing Nan to admit that she’d not done anything to fact-check the book heralded as “brutally honest” in its press release. Three years later, Oprah would apologize to James for confronting him so publicly.

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26. After a 1996 episode about mad cow disease in which Oprah claimed she’d been stopped cold from ever eating another burger, she and her guest Howard Lyman found themselves sued by Texas cattleman in 1998 for “false defamation of perishable food” and “business disparagement.”The claim argued that Oprah’s comments had caused cattle prices to fall, costing beef producers $11 million. After jurors sided with her and rejected the lawsuit, Oprah said, “Free speech not only lives, it rocks,” adding, “I’m still off hamburgers.”

Bryan Bedder/Getty Images for THR

27. In preparation for the trial, Oprah hired the services of Phil McGraw and his legal consulting firm Courtroom Sciences, Inc. (the inspiration for the current CBS drama Bull) to help her analyze the jury. After her victory, she was so impressed with his services that she invited him on her show. So, what we’re saying is that you have Texas cattle farmers to thank for the Dr. Phil show.

KENA BETANCUR/AFP via Getty Images

28. The popularity of The Oprah Winfrey Show in its heyday is also responsible for launching (or boosting) the careers of Dr. Oz, Rachael Ray, Iyanla Vanzant, Nate Berkus, Suze Orman, and, of course, BFF Gayle King.

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29. When Ellen DeGeneres chose to publicly come out as a lesbian on Oprah’s show in 1997, just before her sitcom character did the same to her therapist, played by the talk show host, it earned Oprah some not-so-positive reactions. “I played the therapist on that show… and got the most and worst hate mail of my entire career after doing it, like ‘Go back to Africa’ hate mail,” she admitted in a 2013 episode of her show Oprah’s Next Chapter.

Paras Griffin/Getty Images for Oprah

30. After the Ellen moment, Oprah and Gayle began facing never-ending rumors that they are gay. In the August 2006 issue of O, the mogul shut the chatter down once and for all.”I understand why people think we’re gay,” she wrote. “There isn’t a definition in our culture for this kind of bond between women. So I get why people have to label it—how can you be this close without it being sexual? I’ve told nearly everything there is to tell. All my stuff is out there. People think I’d be so ashamed of being gay that I wouldn’t admit it? Oh, please.”

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