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On the surface, Oprah Winfrey appears to be one of those rare celebrities who’s impossible to dislike. Yet even so, the legendary talk show host has enraged more than her fair share of famous faces over the years. Take these 20 stars, for example – all of whom seem to have had a bone to pick with the woman dubbed the Queen of All Media.

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20. Ludacris

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“It was like being at someone’s house who doesn’t really want you there.” That’s how Ludacris described his 2005 appearance on The Oprah Winfrey Show to promote Best Picture Oscar winner Crash. The hip-hop star made that shocking revelation in a 2006 interview with GQ magazine, saying that he’d been unfairly targeted after Winfrey had called him out for his questionable lyrics about women.

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Ludacris also claimed that Winfrey was anything but the perfect host off air. In the same GQ interview, the Dirty South rapper alleged that many of his comebacks had been cut out of the broadcast. He added, “Of course, it’s her show, but we were doing a show on racial discrimination, and she gave me a hard time as a rapper when I came on there as an actor.”

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19. Angelina Jolie

Winfrey has unarguably become just as renowned for her humanitarian and philanthropic work as her talk show career. And in the 2000s, she added to her list of many achievements when she opened up a South African boarding school designed to help girls from deprived areas to fulfill their potential. But when Winfrey asked for help from a celebrity to promote the academy, the star in question declined the invitation.

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You see, while Angelina Jolie is no stranger to humanitarianism herself, she reportedly felt as though she couldn’t play a part in Winfrey’s project. The Oscar winner was allegedly upset with the way that the talk show host had appeared to take Jennifer Aniston’s side in the tabloid-baiting love triangle involving Brad Pitt.

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18. Seal

“Kiss from a Rose” singer Seal isn’t particularly renowned for courting controversy. In 2018, though, he made headlines by insinuating that Winfrey had been aware of the Harvey Weinstein scandal long before it became public. The vocalist took to Instagram to post a meme that read, “When you have been part of the problem for decades, but suddenly they all think you’re the solution.”

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Seal also used several photos to back up his point – one of which sees Winfrey planting a kiss on the disgraced producer. He accompanied the meme with the message, “Oh I forgot, that’s right… You’d heard the rumors, but you had no idea [Weinstein] was actually serially assaulting young starry-eyed actresses who in turn had no idea what they were getting into. My bad.” Ouch.

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17. Mo’Nique

Mo’Nique’s feud with Winfrey looks to date all the way back to 2010. In the same year that she won the Oscar for her performance in hard-hitting drama Precious, the actress and comedienne agreed to let Winfrey interview her older brother. And during the conversation, Gerald Imes admitted to sexually abusing Mo’Nique as a youngster, backing up his sister’s previous allegations.

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Yet while Mo’Nique may have been consulted about the interview beforehand, she claims that she wasn’t made aware her mother and father would be sitting in the audience, too. The star believes, moreover, that her parents had never grasped the severity of the situation and that Winfrey had betrayed her trust by inviting them onto the set. For her part, the host apparently told the comedienne that she didn’t know her folks would be present. Mo’Nique has also suggested that Winfrey may have had a hand in her having seemingly been snubbed by Hollywood since her Academy Awards victory.

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16. Whoopi Goldberg

Winfrey and Whoopi Goldberg have thankfully managed to patch up their differences in recent times. However, for roughly three decades, the pair barely spoke. The drama began when Goldberg picked up a Best Actress Oscar nod for her performance in The Color Purple – a moment that biographer Kitty Kelley claims upset co-star Winfrey.

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Interestingly, Goldberg never appeared as a guest on Winfrey’s show following the film’s release, while she was also notably absent from the talk show host’s Legends Ball in 2006. But the two ultimately made amends when they bumped into each other at a Tyler Perry party and learned that their apparent beef was all simply a misunderstanding.

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15. 50 Cent

50 Cent incurred the wrath of the talk show queen in 2006 when he described her as an “Oreo” during a chat with Elle magazine. The rapper argued, too, that while Winfrey had “started out with black women’s views, [she] has been catering to middle-aged white American women for so long that she’s become one herself.” And to add insult to injury, 50 also named a pet dog after the TV host.

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However, the two appeared to make up when 50 guested on Oprah’s Next Chapter in 2012. The rapper explained that he’d been upset by Winfrey’s snubbing of hip-hop, revealing, “I would see moments when you would discuss your feelings on the [rap] culture. And everything that was wrong with the culture was what was on my CD, and I was like, ‘Oh, she doesn’t like me.’”

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14. Randy Jackson

It seems that Winfrey probably shouldn’t expect any Christmas cards from Randy Jackson. And that’s despite the fact that the host invited his mom, Katherine, and father, Joe, onto her show in 2010 in the wake of his brother Michael’s death. However, the King of Pop’s sibling was allegedly left seething by the interview – owing, it appears, to Winfrey’s actions five years beforehand.

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You see, in 2005 Winfrey addressed the subject of pedophilia on several episodes of her hit show. This, of course, just happened to be during the same period when Michael was on trial for child molestation. And Randy believes that Winfrey deliberately scheduled these episodes for that time as a ploy to help put Michael behind bars.

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13. Janet Jackson

What’s more, Winfrey apparently added Janet to the list of Jackson family members that she’s riled when she interviewed Michael’s three children in 2010. Allegedly, the “Rhythm Nation” singer was left angry after hearing about the televised chat and subsequently accused Winfrey of exploiting Prince, Paris and Blanket in a quest for ratings. In fact, she reportedly even tried to stop the interview from going ahead.

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And according to the National Enquirer, Janet and Winfrey were at loggerheads shortly before the chat took place. The tabloid reported, “The two women had a blistering blow-up during a telephone call on the day that the show was taped. When Oprah made it clear that she was going ahead with the interview, Janet screamed, ‘Oprah, you make me sick!’”

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12. Rachael Ray

Another daytime talk show stalwart is said to have started an all-out war with Winfrey in 2007. In that year, gossip site TMZ reported that celebrity chef Rachael Ray had made all sorts of derogatory comments about the star during a drunken night out. Perhaps the most damning, however, was the claim that Winfrey had been in “slave drag” while appearing in the 1998 film Beloved.

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Yes, the seemingly mild-mannered Ray reportedly argued that Winfrey had an issue with “being black” as she continued to get more “loud and aggressive.” The star also allegedly described Winfrey as a “demanding b***h,” according to the National Enquirer. Nevertheless, Ray’s camp was quick to deny that such inflammatory insults had ever been uttered.

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11. Chris Brown

In the wake of Chris Brown’s attack on then-girlfriend Rihanna in 2009, Winfrey hosted an episode of her show that tackled the issue of domestic violence. And following the transmission, the R&B singer told People magazine that he felt as though he’d been thrown under the bus. He said, “I did a lot of stuff for [Winfrey], like going to Africa and performing for her school. She could have been more helpful, like, ‘Okay, I’m going to help both of these people out.’”

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A Winfrey representative responded to Brown, however, through a statement that read, “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.” That didn’t placate Brown, who told radio station Hot 97, “As a young black man myself, I need older black male role models to step in and kind of mold me. Not people-bashing me, ’cause that’s not how you learn from mistakes.”

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10. Jonathan Franzen

Winfrey’s relationship with Jonathan Franzen has been turbulent, to say the least. In 2001 the author kicked things off by describing the host’s famous book club as “schmaltzy” and “one-dimensional” while in conversation with Salon. Franzen even took umbrage with Winfrey’s decision to select one of his own novels, The Corrections, telling the website, “I see this as my book, my creation, and I didn’t want that logo of corporate ownership over it.”

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But Franzen later changed his tune and even accepted an offer to appear on Winfrey’s show. He said to The New York Times, “I said things that ended up hurting [Winfrey’s] feelings… I feel bad because the person being hurt is actually a really good person for American writing and reading.”

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9. Roseanne Barr

Roseanne Barr is certainly no stranger to the celebrity feud, and in 2008 she added Winfrey to her list of targets. In particular, the motormouthed comedienne criticized the TV legend for favoring Barack Obama over Hillary Clinton in the Democratic presidential primaries. And on her official website, Barr described Winfrey as a “closeted Republican” who didn’t like “other women who actually stand for something to working American women besides glamour, angels, Hollywood and dieting.”

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However, less than 24 hours later, Barr said sorry for her harsh words towards Winfrey. She wrote, “I got upset because I felt Oprah was adding to the divisiveness in this country. I am sorry, Oprah, I really do admire and love you for all the good you do and have done in this country and the world at large.”

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8. Ice Cube

“She’s had damn rapists, child molesters and lying authors on her show. And if I’m not a rags-to-riches story for her, who is?” It seems fair to say that Ice Cube isn’t particularly happy about seemingly being constantly snubbed by the Queen of All Media. Yes, the rapper has never been asked to be a part of Winfrey’s show, and in 2006 he told FHM that he believes she has a “problem with hip-hop.”

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Ice Cube also referred to the specific occasion when his co-stars Eve and Cedric the Entertainer were both invited to promote the movie Barbershop on the show – but he wasn’t. Yet Eve’s appearance perhaps undermines his argument that Winfrey hates hip-hop. And the media mogul herself even later told MTV, “I’m not opposed to rap. I’m opposed to being marginalized as a woman.”

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7. Joan Rivers

The late great Joan Rivers was never one to hold back, and she certainly lived up to her cutting reputation when she interviewed Winfrey on The Tonight Show in 1985. In her cookbook, Food Health and Happiness, Winfrey recalled the incident – which just so happened to take place during her national TV debut – writing, “I was starting to settle in. And then it happened. Joan interrupted with perhaps the only question I hadn’t prepared for: ‘So, how’d you gain the weight?’”

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“[Rivers] wagged her flawlessly manicured finger at me, pointed out that I was still ‘a single girl’ and challenged me to come back 15 pounds lighter next time she hosted,” Winfrey continued. And Rivers didn’t go any easier on the star over the years, either. Indeed, an insider reportedly once told the National Enquirer that the comedienne believed Winfrey was “the biggest phony in the world.”

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6. David Letterman

In 1995 David Letterman publicly made Winfrey an enemy with a jibe at her expense while hosting the Oscars. He didn’t help matters, either, when he introduced a sarcastic segment on his late-night hit called Oprah Log. Yet Letterman claims that his beef with Winfrey actually began long before the Academy Awards incident.

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In 2010, you see, Letterman told The Daily Show’s Jon Stewart that he had first encountered Winfrey when he was having lunch on vacation with his girlfriend. The star admitted that as a joke he had told the waiter, “Oh, this woman right over there [Winfrey] has been kind enough to take care of our check. We got a free lunch, and that’s where it started.” Finally, though, the pair patched up their differences in 2005.

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5. James Frey

James Frey no doubt rues the day that he ever agreed to appear on The Oprah Winfrey Show. By then, the writer had already topped The New York Times’ Best Sellers list with his 2005 semi-fictionalized memoir A Million Little Pieces – largely thanks to Winfrey’s seal of approval. However, after Frey graced the show, website The Smoking Gun decided to research his story, with the investigation ultimately discovering that much of the information presented in the book as fact had been entirely fabricated.

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Then, when Frey returned to the show at the start of 2006 to explain his actions, Winfrey said that he’d “betrayed millions of readers.” The TV icon embarrassed the author’s publisher, Nan Talese, to boot when she also appeared on set to justify the book being marketed as an autobiography. Talese would later criticize Winfrey for her “fiercely bad manners.”

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4. M.I.A.

In 2009 Winfrey met pop provocateuse M.I.A. at a Time magazine party honoring some of the 21st century’s most influential people. Yet it seems that their encounter didn’t exactly go swimmingly. Recalling the incident in a 2015 interview with Rolling Stone, M.I.A. said that she had asked Winfrey to help shine the spotlight on the oppressive regime of her native Sri Lanka. However, it’s claimed that the TV icon had little interest in talking to someone who had previously been so “rude to Lady Gaga.”

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M.I.A. alleged, “[Winfrey] shut me down. She took that photo of me, but she was just like, ‘I can’t talk to you because you’re crazy and you’re a terrorist.’ And I’m like, ‘I’m not. I’m a Tamil, and there are people dying in my country. And you have to, like, look at it because you’re f**king Oprah, and every American told me you’re going to save the world.’”

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3. Iyanla Vanzant

Iyanla Vanzant apparently clashed with Winfrey in 1998 following a misunderstanding about a new talk show. After appearing on the host’s series to promote her book In The Meantime, the inspirational speaker subsequently became a protégée of the TV legend. But unfamiliar with how the industry worked, Vanzant ended up cutting her ties with Winfrey when she approached the other woman to help her launch her own vehicle.

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Vanzant told syndicated U.S. radio show The Breakfast Club, “I was just being naive and stupid and asking, but it wasn’t received well. And that created a breakdown in communication. But we were able to repair that. It took 11 years… They didn’t think I was ready [for my own show], but that was never communicated to me.”

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2. Toni Braxton

Toni Braxton certainly didn’t appreciate Winfrey’s opinion when she went bankrupt for the first – but not the last – time. In particular, the R&B singer was chastised by Winfrey for possessing Gucci cookware in her kitchen at a time of serious financial trouble. And Braxton hit back as a result, calling the TV star “so frickin’ mean” in a 2012 episode of Behind The Music.

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In fact, Braxton even went on to claim that Winfrey had made a damaging impact on her career. Several years later, however, the chart-topping singer appeared to let bygones be bygones. In any case, Braxton agreed to portray unsung hero Darlene Love in a TV movie biopic screened on Winfrey’s OWN network.

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1. Anjelica Huston

Winfrey doesn’t appear to be a particularly gracious loser, according to Anjelica Huston. In an interview with New York magazine, the actress revealed that Winfrey had reportedly snubbed her ever since the pair had gone head to head in the same Oscars category in 1986. On that occasion, Huston ended up winning the Best Supporting Actress gong for her turn in Prizzi’s Honor – and apparently Winfrey has never forgiven her for it, either.

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Huston added, “The only encounter I’ve had with Oprah was when I was at a party for the Academy Awards [at] a private residence. I was talking to Clint Eastwood, and [Winfrey] literally came between us with her back to me. So all of the sudden I was confronted with the back of Oprah’s head. Nobody else would dislike me so much as to literally, physically come in between the person I was talking with that way.”

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