Oprah’s Biggest Moments

She's a force of nature and about to leave daytime TV. We take a look at key moments in Oprah's decades-long career.

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","id":"2084139","thumbnail_url":"https://nbcots.go-vip.co/wp-content/uploads/2019/09/oprahjumpthumb.jpg?fit=722%2C406","type":"image","focusedSlide":""},{"caption":"Talk show queen Oprah Winfrey has signed off for good. Among the top “Oprah” moments from the past 25 years: Tom Cruise bouncing on Winfrey’s couch to proclaim his love for Katie Holmes in 2005. Check out more surprises, scandals and milestones in Oprah's career.
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Tom Cruise returned to the show Tuesday night for a star-studded double-taping of "Surprise Oprah! A Farewell Spectacular" in Chicago's United Center. The shows will air May 23 and May 24 and ahead of Winfrey's final show. Madonna and Beyonce also stopped by.
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Oprah earned both Academy Award and Golden Globe nominations for best supporting actress for her performance in "The Color Purple." The 1986 film, adapted from Alice Walker's 1982 novel of the same name, ran as a Broadway musical from late 2005 to early 2008.
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In 1988, Oprah wiggled her way into size 10 jeans and dragged a red wagon holding 67 pounds of fat on stage. It represented the weight she lost on a four-month-long liquid diet. She put weight back on as soon as she started eating again, and told "Good Morning America" the wagon bit was "an iconic mistake."
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In 1988, Oprah interviewed Elizabeth Taylor. Before the interview, the seven-times-married Taylor asked that Oprah not ask anything about her love life. To try to break the tension, Oprah teased, "I declare, you've got to stop talking so much, Ms. Taylor!" Here they are in 2002, looking slightly more friendly.
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In 1993, Michael Jackson welcomed Oprah to the Neverland Ranch for his first interview in 14 years. It became known as the "definitive Michael Jackson interview," where Jackson revealed intimate details about his skin color, plastic surgery, relationships and love for children.
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Oprah showed considerable relief after a jury ruled in her favor following a two-month-long defamation trial of the Texas beef industry, claiming it cost them millions of dollars. Oprah had said a guest's account of cattle being fed to other cattle as feed "just stopped me cold from eating another burger."
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Mary Tyler Moore - one of Oprah's early role models -- surprised Ms. O with a live call to the show in 1997. Oprah was stunned when Moore walked on stage. "I am still in awe of a woman whose life is an example of grace and sensitivity," Oprah wrote on her website.
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Dr. Phil first appeared on "Oprah" in the last '90s. Viewers liked him so much that he appeared every week as a "relationship and life-strategy expert." He got his own show in 2002.
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Oprah's Book Club began in 1996 and turned obscure titles into overnight bestsellers. Authors and publishers rejoiced ...
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... with the exception of Jonathan Franzen. When his novel "The Corrections" was selected for the Book Club, Franzen called many of her selections "schmaltzy" and "one-dimensional," and said he wanted to attract a more male audience. His book was promptly kicked out of the club. The author and the interviewer buried the hatchet in September 2010, when Franzen's book "Freedom" became a Book Club pick.
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After it was revealed in 2006 that Book Club author James Frey invented and embellished parts of his so-called memoir, "A Million Little Pieces," Oprah confronted him on the air. "I feel duped," she said. "But more importantly, I feel that you betrayed millions of readers." Frey's career has since recovered, but he lost a book deal in the aftermath.
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Oprah also made Dr. Mehmet Oz a star. The Turkish-American cardiothoracic surgeon first appeared on the show in 2004.
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Food guru Rachael Ray's career got a jump start from Oprah. Her own daytime show premiered in 2006.
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One of Oprah's "favorite spiritual teachers" was a boy with muscular dystrophy. Mattie Stepanek published five books of poetry and advocated for peace. In a 2000 appearance on the show he shared his personal philosophy: "Play after every storm." Stepanek passed away in 2004 at age 14. Here he is with his mother Jeni Stepanek.
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Legendary actor Sidney Poitier visited Oprah's show in 2000, after his autobiography was published. Oprah said she broke down in tears after her interview with him. "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," she wrote on her website.
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Tina Turner and Oprah Winfrey boogie at the 2000 launch party for "O, The Oprah Magazine." Oprah said she had always dreamed of singing onstage with the famously coiffed singer.
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The thing about "O: The Oprah Magazine" is that Oprah is on <i>every single cover</i>. She's shared the front page twice since it's launch in 2000: once with Ellen DeGeneres and once with Michelle Obama. Here's the September 2001 cover.
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Every audience member at a September 2004 show went home with a free Pontiac G6. Oprah said the spectators were selected because each person needed a car. EMTs were standing by in case anyone had heart problems, Oprah said on her website.
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Here's Oprah at the opening ceremony of her $40 million Leadership Academy for Girls School outside Johannesburg, South Africa. The school was rocked by a sex scandal shortly after it opened in 2007. A woman working at the school was charged with sexual assault and later cleared of all charges. Oprah said she was "profoundly disappointed" by the trial's outcome.
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In 2008, Oprah produced "The Secret Life of Bees," based on Sue Monk Kidd's novel. The film is set in South Carolina in 1964 and features Queen Latifah, Alicia Keys and Dakota Fanning.
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Suze Orman first showed up on "Oprah" as a personal finance expert, offering advice on debt, marriage and planning. On one February 2008 show, she gave away a million electronic copies of her book "Woman and Money." Here she is with Oprah and Whoopi Goldberg.
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Mackenzie Phillips, daughter of the Mamas & the Papas' singer Jon Phillips, appeared on Oprah in 2009 and spoke for the first time about her cocaine-fueled, incestuous relationship with her father. Her book, "High on Arrival," describes her struggle with drug abuse and her 10-year-long sexual relationship with her father.
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In May 2009, Oprah teamed up with KFC to promote their new grilled chicken. She said anyone could print a free coupon and get two pieces of chicken, two sides and a biscuit for free. Turns out she underestimated the people's desire for free fast food. Some locations turned people away because they didn't have enough to go around.
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Oprah was an executive producer of "Precious," a brutal drama about abuse and poverty. Here she is with executive producer Tyler Perry and Oscar-nominated star Gabourey Sidibe at the 2009 Toronto Film Festival. "None of us who sees the movie can now walk through the world and allow the Preciouses of the world to be invisible," Winfrey told reporters there.
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The guest list for the final show is being kept a secret, even from Oprah herself. In December 2010, Aussie Hugh Jackman flew down a zip-line cable, colliding with a lighting rig and injuring his right eye. Jackman emerged with a smile, and Oprah offered him a hug and a glass of wine for his trouble.
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Lady Gaga tried to turn Oprah into one of her little monsters in a January 2010 appearance on Oprah's show.
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President George W. Bush sat down with Oprah in November 2010 to discuss his presidency and his past. He spoke about war, Hurricane Katrina and his former alcoholism.
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Oprah's famous best friend, Gayle King, works as editor-at-large for "O: The Oprah Magazine." In a December 2010 interview with Barbara Walters, Oprah addressed rumors that she and King are a couple: "I'm not a lesbian. I'm not even kind of a lesbian." Then, she burst into tears and called to an off-camera minion, "I now need tissue!"
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A show, magazine and production company weren't enough? The Oprah Winfrey Network launched on Jan. 1, 2011. The final episode of "The Oprah Winfrey Show" is set to air May 25, after 25 years on the air.
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