Oprah Winfrey may be the most beloved celebrity of all time. She took her successful talk show and transformed it into an entire lifestyle brand. Along the way, Oprah has used her platform to propel various authors, celebrities, and projects to greater success. On top of that, she is renowned as a philanthropist and has donated millions of dollars to charity.
Not everyone loves Oprah, though. In fact, there are some celebrities that can’t stand her. Here’s a definitive list of the celebs secretly holding major grudges against Oprah.
David Letterman
You might expect David Letterman and Oprah to get along because they are both beloved talk show hosts and entertainers. However, they have a pretty ancient beef, along with different stories of how it got started.
In an interview with Jon Stewart, Letterman revealed that their feud started even before he made a joke about Oprah’s name when he hosted the Academy Awards in 1995.
“This predates the Academy Awards. She hated me long before then,” Letterman said. “She was with Steadman, I was with my then-girlfriend Regina. We were both at a restaurant having lunch on vacation. I said to Regina, ‘Oh, this is hilarious, I’m gonna make Oprah buy us lunch.’”
Letterman told the water, “Oh, this woman right over there has been kind enough to take care of our check,” and even waved at Oprah when he left.
“We got a free lunch and that’s where it started,” he said.
Meanwhile, Oprah told CBS that the beef came from her feeling uncomfortable as a guest on Letterman’s show. She avoided speaking to him for 16 years after that, all while Letterman kept making jokes about her on his show.
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Whoopi Goldberg
If we’re being honest, most beefs boil down to simple misunderstanding. And that’s definitely the case when it comes to Oprah and Whoopi Goldberg.
According to Kitty Kelley’s biography of Oprah, Oprah began snubbing Goldberg after she was nominated for an Academy Award for The Color Purple. Oprah’s performance in the same film was overlooked by the Academy.
Whatever the reason, Whoopi was never invited to Oprah’s show again and was not part of Oprah’s Legends Ball.
But when they ran into each other at a Tyler Perry house party in 2010, Oprah confessed she thought Goldberg was mad at her.
“I’m going to try not to cry,” Oprah said when she revealed the story of their reunion to the public, according to Oprah.com. She explained that Whoopi asked her, “Did I do something to you? All these years, we’ve been disconnected, and I just want to know, did I do something?”
“You think I’m mad at you?” Oprah said. “I thought you were mad at me.”
In other words, it was a decades-old misunderstanding! And it seems this pair has finally made up.
Chris Brown
Some of these celebrity feuds are more one-sided than others. And there are some where it’s clear that Oprah was 100% right.
That’s the case with musician Chris Brown. After he assaulted Rihanna in 2009, Oprah aired a special domestic violence episode and did not mince her words at all. Addressing Rihanna, Oprah made it clear: “He will hit you again.”
Afterward, Brown told People that he considered this “a slap in my face.” He was angry that Oprah wanted to help Rihanna only and not the both of them. And Brown brought up that “he did a lot of stuff for [Oprah], like going to Africa and performing for her school.”
Oprah politely rebuked that she takes domestic violence very seriously.
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Seal
Being as famous as Oprah means making many famous friends. But what happens when those friends do the unthinkable?
That was on Seal’s mind when he posted multiple photos of Oprah and Harvey Weinstein on his Instagram. And he went so far as to caption the photos with, “Oh I forgot, that’s right… you’d heard the rumors but you had no idea he was actually serially assaulting young starry-eyed actresses who in turn had no idea what they were getting into. My bad.”
According to Business Insider, Seal later walked his statements back, but the damage was done.
Angelina Jolie
Many of these beefs with Oprah come down to a case of “he said, she said.” And that seems to be what happened with Oprah and Angelina Jolie.
When the talk show mogul was launching the Oprah Winfrey Leadership Academy for Girls, she invited Jolie to help with the launch. But according to an insider (via Fox News) familiar with the beef, Jolie refused. Allegedly, it was because she saw Oprah as taking Jennifer Aniston’s side when the Friends star split with Brad Pitt.
Regardless of the cause, the source claims Oprah will never ask Jolie to help with anything else.
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50 Cent
Oprah’s fame eventually reached a kind of critical mass. Her thoughts and opinions shaped entire generations’ perspectives. And rapper 50 Cent had some objection to some of those thoughts, going so far as to name his dog “Oprah” as a form of revenge.
What made him so mad? In a 2006 issue of Elle magazine (via TMZ), 50 Cent called Oprah someone who “started out with black women’s views but has been catering to middle-aged white American women for so long that she’s become one herself.”
They had a breakthrough six years later on an episode of Oprah’s Next Chapter. There, 50 Cent admitted that he took Oprah’s disdain for rap and rap culture as a rejection of him and his lifestyle. And he felt, “If I can’t be your friend, at least let me be your enemy.”
Ludacris
In fact, Oprah’s disdain for rap and hip-hop has created more than one beef. And her disdain is at the center of the beef that Ludacris has with the famous talk show host.
Back in 2004, Oprah invited Ludacris on her show ostensibly to promote his new movie Crash. Instead of focusing on his thoughts, though, the interview was heavily edited and cut out most of the singer’s remarks.
He later told GQ that he gleaned a sad truth from talking with Oprah after the interview.
“What I got was that by having rappers on her show, she feels like she’s empowering them… It was like being at someone’s house who doesn’t really want you there. It was already uncomfortable.”
Ludacris also felt Oprah was a hypocrite because she disliked his use of offensive language in his music while she still invited comedians who use such language (such as Chris Rock and Dave Chapelle) on her show. He concluded, “They speak the same language as I do, but they do it through comedy, so I guess that’s acceptable to her.”
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Roseanne Barr
Of all the beefs on this list, Roseanne Barr’s beef with Oprah may be the weirdest. But that has everything to do with how much Barr has changed over the years.
Back in 2008, Oprah endorsed Barack Obama for the Democratic presidential candidacy instead of Hillary Clinton. This unhinged Barr, who used her personal website to unload on Oprah.
According to Fox News, Barr called Oprah “a closeted Republican” who opposed Hillary Clinton “because you do not like other women who actually stand for something to working American Women besides glamour, angels, Hollywood and dieting.”
Barr apologized the next day on the same site, claiming that she loves Oprah and merely got carried away by her preference for Hillary Clinton over Barack Obama. But Roseanne Barr would later become one of President Trump’s biggest fans and cheerleaders even as she shared right-wing conspiracy theories via Twitter.
In other words, her beef against Oprah as “a closeted Republican” may have been a classic case of projection!