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As the 2008 presidential elections heated up, Oprah made her endorsement of current President Barack Obama quite clear. But Roseanne Barr, for one, was not happy about it. “Oprah has given us Swartzenegger [sic] and Dr. Phil. If that was not offensive enough to decent thinking people, now she brings us Obama,” Barr blogged. Then, to Winfrey, she added: “You are a closeted republican and chose Barak [sic] Obama because you do not like other women who actually stand for something to working American Women besides glamour, angels, Hollywood and dieting!” But, in one of her many final season hatchet-burying episodes, Winfrey had Barr on to discuss, among other things, the Obama battle. “I thought maybe you were mad at me because I got mad at you for choosing Barack Obama over Hillary Clinton and I said so. I thought, 'Uh-oh, she's going to really be pissed off at that,’” Barr told Winfrey. The talk-show host replied, “I will assure you, I wasn't even the least bit affected by it… Lots of people were pissed off at the time." (AP Photo) See the Full Story at The Daily Beast
In her 25 years on "The Oprah Winfrey Show," the daytime talk-show billionaire has had rumored conflicts with everyone from the first lady to Oscar winners to a legendary battle with David Letterman. See the best of the worst. (AP Photo/Chris Pizzello, File) See the Full Story at The Daily Beast
Kitty Kelley spent three years and 850 interviews on her unauthorized Oprah biography, released in spring 2010. Kelley said that despite her book's juicy revelations, she couldn't get Barbara Walters, Larry King, Rachael Ray, or Charlie Rose to give her an interview. "Even David Letterman, who's had a 16-year feud with her, said ‘I don't really want to disrupt the relationship I now have with her," Kelley said. Oprah responded to Kelley's book only indirectly, at an awards show where she honored her longtime friend Gayle King. Confessing she'd had a busy week thanks to the publication of "my so-called biography," Oprah said, "Gayle got herself worked out with all my new daddies coming out," a reference to Kelley's claim that Vernon Winfrey isn't her biological father. "This, too, shall pass." (Jeff Christensen/AP Photo) See the Full Story at The Daily Beast
Oprah "had no idea that Michelle was so jealous about the influence she had on Barack," a "friend" told The National Enquirer. The first lady "hated the way her husband would huddle with Oprah over strategy and jump when she called… The jealousy and anger was eating up Michelle. During the campaign, she vowed Oprah would not be a part of the new administration." And thus the talk-show host was frozen out of the president's inner circle, the tabloid claims. But the Obamas and the big O herself have seemingly made up to make history: The couple became the first and the last sitting president and first lady to appear together on "The Oprah Winfrey Show." (Carolyn Kaster/AP Photo) See the Full Story at The Daily Beast
The fray over Frey began when Winfrey picked his memoir "A Million Little Pieces" as the September 2005 selection for her book club. The work topped The New York Times' bestsellers list shortly thereafter. But the more Frey and his work were subjected to scrutiny, the more it became clear the writer had fabricated parts of his memoir—like the key scene, in which he was arrested. Unluckily for him, Oprah's payback was a you-know-what. Frey returned to the show to apologize publicly, and a no-nonsense Oprah told it like it was: "I feel you betrayed millions of readers." She wasn't content, however, just to chastise Frey. She brought on the book's publisher, Nan Talese, and got her to admit that she had never fact-checked the memoir. As her show came to a close in May 2011, Winfrey again sat down with Frey and the two hugged it out. (Ulf Andersen/Getty Images) See the Full Story at The Daily Beast
Think taking sides in celebrity tabloid sagas has no consequence? Think again. Oprah thought that Angelina Jolie, for all her charity work in Africa, would be happy to help promote Oprah's school for girls in South Africa. It was not to be. Oprah was publicly on Team Aniston when Brad Pitt broke up with Jen for Jolie. Oprah declared "it's the last time she'll ask Angelina to help with any of her causes," a source told Star. (Joel Ryan/AP Photo) See the Full Story at The Daily Beast
Though she wasn’t the first to speculate that Oprah Winfrey and Gayle King are more than best friends, out lesbian Rosie O’Donnell told Howard Stern that the Winfrey and her longtime friend are “the emotional equivalent” of a gay couple, even if she doesn’t know if they’re “doing each other.” O’Donnell added: “I don't mean it to be an insult either.” But rumors began flying that Oprah didn’t like it. “Rosie should know better,” a Winfrey associate allegedly told the Chicago Sun-Times. But there seemed to be no hard feelings when Winfrey announced that O’Donnell would return to the hosting seat on a new series on Winfrey’s OWN and is taking over Winfrey’s longtime studio. The boss took to Twitter to set the story straight. “There's no feud between Rosie and me,” Winfrey tweeted. “I get so sick of people trying to create fights and feuds when women are in business. Don't buy into it.” (AP Photo) See the Full Story at The Daily Beast
In 2001, when Jonathan Franzen's wildly popular novel "The Corrections" was selected for Oprah's Book Club, Franzen, though not entirely bothered by the book's selection, was not necessarily happy about it, either. "She's picked some good books," Franzen said of Oprah in an interview posted on Powells.com, "but she's picked enough schmaltzy, one-dimensional ones that I cringe." Salon.com's Laura Miller described the novelist's slight this way: "Oprah's selection of 'The Corrections' was a bold, generous choice for a book that is also bold and generous. If the author has on this occasion lacked the nerve and imagination of his creation, well, writers are human beings, too, and sometimes they screw up. The books are what matter, if we could just manage to remember that." Nearly a decade after the controversy, Winfrey announced Franzen's novel "Freedom" would be an Oprah Book Club selection and a few months later, the two sat down on "The Oprah Winfrey Show" to hash out their differences. "The big thing I learned from the experience, was to have more respect for television," Franzen admitted during the December 2010 episode. (Stuart Ramson/AP Photo) See the Full Story at The Daily Beast
In the wake of the tragic death of pop legend Michael Jackson, his three children were thrust into the media spotlight. Oprah interviewed the children and Jackson’s youngest sister Janet wasn’t happy about it. According to the New York Daily News, she “didn’t think the kids should have done it.” The National Enquirer also made similar claims, alleging a source told the tabloid that Janet was “furious” that Winfrey “took advantage” of Michael's children for ratings, using them as “pawns.” On the day the show was filmed in 2009, Jackson reportedly called Oprah and told her, “You make me sick!” Neither Winfrey nor Jackson confirmed the rumors, but nine months later, Jackson appeared on "The Oprah Winfrey Show" to talk about her brother’s passing and her niece and nephews. "They're dealing with it," Jackson told Oprah. (Kevin Mazur, WireImage/Getty Images) See the Full Story at The Daily Beast
As the 2008 presidential elections heated up, Oprah made her endorsement of current President Barack Obama quite clear. But Roseanne Barr, for one, was not happy about it. “Oprah has given us Swartzenegger [sic] and Dr. Phil. If that was not offensive enough to decent thinking people, now she brings us Obama,” Barr blogged. Then, to Winfrey, she added: “You are a closeted republican and chose Barak [sic] Obama because you do not like other women who actually stand for something to working American Women besides glamour, angels, Hollywood and dieting!” But, in one of her many final season hatchet-burying episodes, Winfrey had Barr on to discuss, among other things, the Obama battle. “I thought maybe you were mad at me because I got mad at you for choosing Barack Obama over Hillary Clinton and I said so. I thought, 'Uh-oh, she's going to really be pissed off at that,’” Barr told Winfrey. The talk-show host replied, “I will assure you, I wasn't even the least bit affected by it… Lots of people were pissed off at the time." (AP Photo) See the Full Story at The Daily Beast
Chris Brown was upset last year when Oprah dedicated an entire show to domestic violence and "all the Rihannas of the world." He expressed his displeasure (rather inartfully) when he told People, "I commend Oprah on being like, 'This is a problem,' but it was a slap in my face." Brown had performed at Oprah's girls' school in South Africa, and thought that would have earned him a reprieve from her scrutiny after he allegedly hit his then-girlfriend Rhianna. The talk-show host's spokeswoman responded, "Oprah is very appreciative that Chris Brown performed at her school, but she takes domestic abuse very seriously... She hopes he gets the counseling he needs." Brown went on to tell New York’s Hot 97 radio station that he hoped Winfrey would "reach out to me and talk to Rihanna... not even to be on the show; just make it about helping. Because at the end of the day I thought we had that type of relationship where it could be like that." (Katy Winn/AP Photo) See the Full Story at The Daily Beast
A little drink has been the downfall of so many. Rachael Ray was having dinner with friends in a Los Angeles restaurant and, after reportedly downing four glasses of red wine, got a little loose-lipped about Oprah, who runs her show's syndication company. Ray started complaining about Oprah, talking about a portrait of the talk-show host that hangs in the lobby of Harpo Productions in Chicago. In the picture, Oprah faces away from the camera, her back exposed and covered with (fake) scars, while wearing a pre-Civil War-style skirt. "Why is she wearing slave drag?" Ray blabbed. "She obviously has problems being black." Ray's camp denied she made the comments. Shortly thereafter, Oprah's best friend Gayle King appeared on Ray's show and the two talked about tabloid rumors. "The one with Oprah just broke my heart," Ray said. "It really did. It killed me, I’m like,‘No! We like each other!'" (Chris Pizzello/AP Photo) See the Full Story at The Daily Beast
Oprah snubbed Whoopi Goldberg when Winfrey hosted her Legends Ball to honor successful black women and didn't invite the comedienne. Both parties said there was no dispute between them, but Whoopi's absence felt significant, given that the pair worked together on The Color Purple and that far lesser stars like Brandy and Audra McDonald showed up. As her show came to a close, Oprah invited the cast of "The Color Purple" on her show for a reunion, including Goldberg. On the episode, Winfrey recalled running into Goldberg at director Tyler Perry's home the summer prior when "The View" co-host came up to her and said, "Can I just ask you something? Did I do something to you? All these years, we've been disconnected, and I just want to know, did I do something?" Oprah recalled replying, "You think I'm mad at you? I thought you were mad at me." (Evan Agostini/AP Photo) See the Full Story at The Daily Beast
Joan Rivers reportedly told friends that she wished she'd been contacted by Oprah biographer Kitty Kelley—she could have offered some real dirt. "Oprah—if she don't need you, she don't know you!" an unnamed friend quoted Rivers as saying, in The National Enquirer. The friend said Rivers thinks the talk-show host is "completely opportunistic," and her "real gift is exploiting people's suffering and emotions and turning them into TV ratings." (Charles Sykes/AP Photo) See the Full Story at The Daily Beast
"Precious" star Mo'Nique was furious when Oprah interviewed the Oscar-winning actress' brother Gerald Imes, who Mo'Nique says molested her. Mo'Nique thought the interview went too easy on Imes, and that he got away with mischaracterizing what happened. Imes was planning to write a book about his childhood, thereby profiting from the actress' pain. Eventually, Mo'Nique forgave Oprah, but her family, of course, is another story. (Mark Terrill/AP Photo) See the Full Story at The Daily Beast
David Letterman is known for his feuds, but none has lasted as long as his nearly two-decade tangle with Oprah. By most accounts, it started when Letterman hosted the Oscars in 1995, and used her name for his failed "Uma, Oprah; Oprah, Uma" joke. In 2005, Letterman finally settled the skirmish when Oprah went on his show as a guest and told him, "I want you to know, it's really over, whatever you thought was happening." But is it? Last September, Letterman told Jon Stewart that the feud actually began when he was having lunch in the same restaurant as Oprah and Steadman while on vacation. As a gag, the late-night host told the waiter that Winfrey’s table was picking up his check; but apparently, Oprah didn't think the joke was funny. "I spent the last 12 to 15 years kissing up to Oprah,” Letterman admitted on "Late Show" this month after he wasn't invited to Winfrey's finale extravaganza in Chicago. “Honest to God. Every day, I get out of bed and I think, What can I do to suck up to Oprah?" In regard to his lack of invite, Letterman said he was "crushed. Disappointed and crushed. I want to bask in the glory that is Oprah, who doesn’t?" (MJames Devaney, WireImage/Getty Images) See the Full Story at The Daily Beast
Oprah took rapper Ludacris to task for his musical misogyny, asking him why he peppers his songs liberally with words like "bitches" and "hos." Ludacris had gone on her show to promote his work in the film "Crash." Of the interview, Ludacris told GQ magazine "she gave me a hard time as a rapper when I came on there as an actor… It was like being at someone's house who doesn't really want you there." Oprah has been given grief by many in the hip-hop world for ignoring their music and for instead pandering to Middle American housewives. Oprah told MTV, "I'm not opposed to rap. I'm opposed to being marginalized as a woman." (Donald Traill/AP Photo) See the Full Story at The Daily Beast
