The Shady Side Of Oprah Winfrey

The inimitable Oprah Winfrey might be known as the Queen of Media, having built up a cross-platform empire — see everything from Oprah Radio and O, The Oprah Magazine to Harpo Films and Oprah.com — worth more than a staggering billion dollars. But you might not necessarily expect the talk show legend to be the Queen of Shade.

After all, the TV personality is renowned for advocating kindness, assisting others both in a financial and self-help sense, and for her compassionate interviewing technique, whether she's interviewing members of the public or members of the royal family. And let's not forget all the multiple Humanitarian Awards she has to go along with all the Emmys.

And yet, even a fairy godmother-like figure, Winfrey still has her moments. From mocking Hollywood legends and belittling supermodels to political quips and family conspiracies, here's a look at 14 times the daytime legend played against type.

As one of Hollywood's most famous gift-givers — who could forget the time she gave each member of her entire chat show's audience a free car? — Oprah Winfrey is inevitably often asked for advice about the perfect present. Unfortunately, as a woman with a reported net worth of $3.5 billion, she's not always in tune with the general public's budget.

In a video clip that circulated on TikTok, Winfrey is asked by a fan about what to get his unwell mother. After racking her brains, the talk show legend suggested a particular red jewelry box she believed retails around the hundred-dollar mark. While that may have been small change to her, $100 was still a significant amount for the man in question. And when he asked if she could recommend something cheaper, the star responded in a rather patronizing fashion, "Lower than $100?"

Although Winfrey did come up with something that cost virtually nothing — a hand-made card featuring a list of 10 loving sentiments — she was still criticized by many viewers for her demeanor. "She said, 'Oh you poor? I got a better gift for you,'" read one sassy comment (via Mirror).

Oprah Winfrey waded into the ongoing argument about the use of weight loss drug Ozempic in 2023 during an episode of Oprah Daily's "The Life You Want: The State of Weight." The talk show legend told a panel of obesity medics that she'd never considered taking it, even when the going got really tough. 

Winfrey explained (via the Independent), "When I first started hearing about the weight loss drugs, at the same time I was going through knee surgery, and I felt, 'I've got to do this on my own.'" "The Color Purple" star was then accused of throwing shade at those who do take it when she added, "Because if I take the drug, that's the easy way out."

"You all know I've been on this journey for most of my life," she went on to add. "My highest weight was 237 pounds. I don't know if there is another public person whose weight struggle has been exploited as much as mine over the years. Shouldn't we all just be more accepting of whatever body you choose to be in? That should be your choice."

Oprah Winfrey's normal people skills were called into question again in 2006 following a cooking segment on her "The Oprah Winfrey Show." The chat show host had invited Anna Ginsberg onto the set after she scooped a colossal $1 million for winning a national culinary contest. Unfortunately, the dish that helped earn her the prize didn't appeal to be Winfrey's taste.

"Do you like it? I hope so," Ginsberg asked about the chicken and spinach stuffing meal she'd just created for one of the world's most famous women. Although Winfrey insisted that she did like it, her face told a different story. And the situation got even more awkward when the Oscar nominee suddenly said, "Did we add salt and pepper? I think we needed salt and pepper."

After the offending clip suddenly went viral several years later, Winfrey decided to issue a defense of her "MasterChef" smackdown on Oprah Daily: "Here's the deal, this is what I was thinking. I always wanted anybody who came on the show no matter what they did to have a good experience. And I also wanted to stay in my own truth while also allowing them to have a good experience ... Because the truth, for me, was that I am used to having salt and pepper on my chicken. That's just the truth."

Purported to be a memoir about his own experiences with addiction, James Frey's "A Million Little Pieces" got the Oprah Winfrey seal of approval in 2005 when it was selected for her prestigious book club. But just a few months later, the author was exposed by The Smoking Gun for fabricating many of his stories, including his apparent criminal activities.

Of course, you mess with America's favorite chat show host at your peril. Incensed at being hoodwinked into promoting what largely turned out to be a work of fiction, Winfrey invited Frey onto her set to give her a piece of her mind: "I don't know what is true and I don't know what isn't," she said, going on to further shade the writer by labeling him as "Mr. Bravado tough guy."

In fact, Winfrey was deemed to be so mean by the general public she felt compelled to ask him back for a third interview. Frey admitted that he'd felt like the victim of an ambush during his previous appearance, but the pair eventually made amends.

In 2013, Oprah Winfrey landed one of the scoops of the year when Lance Armstrong confirmed that all the stories of his performance-enhancing drug use were true. The disgraced cyclist, who'd already lost the majority of his endorsement deals, each and every Tour de France title, and the general respect of the public, revealed in his interview with the talk show legend that he would have found it impossible to achieve his success without resorting to cheating.

Winfrey seemed taken aback by many of his revelations, even letting out a gasp of incredulity when Armstrong stated that he didn't feel like he was gaining an unfair advantage over his rivals, insinuating that his fellow competitors were also adopting similar methods.

But while promoting the face-to-face chat, the TV personality didn't seem entirely convinced that Armstrong had told the truth, the whole truth, and nothing but the truth. Speaking to "CBS This Morning," Winfrey argued that the sportsman "did not come clean in the manner I expected ... I feel that he answered the questions in a way that he was ready."

Before emerging victorious in the 2016 presidential election, Donald Trump claimed that none other than Oprah Winfrey would be his first choice for the role of vice president back in 1999. Unsurprisingly, considering her endorsements for Barack Obama and then Hillary Clinton, the talk show legend wasn't interested in playing second fiddle to the business tycoon.

When asked about Trump's comment during an appearance on "Jimmy Kimmel Live" (via The Daily Beast), a humble Winfrey claimed that it was only a joke. But if an offer truly was put on the table, she would respond, "Donald, I'm with her."

After Kimmel argued that she would win the presidential race over both Clinton and Trump, Winfrey insisted she had no political ambitions: "... The one thing that I know for sure, sure, sure, is I will never run for office." But after acknowledging that she had no qualifications for the job, the billionaire — perhaps suddenly remembering who was in the real running — appeared to have a sudden change of heart: "I'm feeling pretty qualified. After this year, I'm feeling really qualified."

In 2009, Oprah Winfrey dedicated an entire episode of her eponymous chat show to domestic violence. The star felt compelled to address the subject following the news that Rihanna had reunited with Chris Brown, the R&B singer who'd only recently been charged for assaulting her. "Love doesn't hurt," the talk show legend said (via MTV) before adding, "and if a man hits you once, he will hit you again. I don't care what his plea is; he will hit you again."

Of course, not everyone appreciated the episode, which Winfrey explicitly stated was dedicated "to all the Rihannas of the world." Brown told People (via Entertainment Weekly), in a rather unfortunate use of words, that it felt like "a slap in my face." He continued, "I did a lot of stuff for her, 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.'"

To her credit, Winfrey refused to placate Brown. A representative for the billionaire sent Entertainment Weekly the response, "Oprah is very appreciative that Chris Brown performed at her school but she takes domestic abuse very seriously." The statement concluded with some advice, which could also be construed as the perfect bit of shade. "She hopes he gets the counseling he needs."

In 2004, Mary-Kate and Ashley Olsen, then only 17 years old, were invited to appear on "The Oprah Winfrey Show" to promote their big-screen vehicle, "New York Minute." Considering their young age, you may have expected the talk show host to be a little more sensitive when it came to the sensitive issue of weight — there were rumors at the time that Mary-Kate had developed an eating disorder. Instead, Winfrey went all guns blazing.

When asked specifically about the gossip, Ashley responded, "Yeah, you know people are going to write what they're going to write. We try not to read the good or the bad because it just comes with the territory. Either you're too fat, too skinny and people are just gonna write what they ..." But before the former "Full House" star could finish her sentence, Winfrey waded in with, "What size are you, by the way?"

Taken aback by the rather blunt line of questioning, the twins refused to give an exact figure, with Mary-Kate simply replying that she and her sister had always been petite. "That's so interesting," Winfrey responded with a hint of sarcasm before adding, "I'm obsessed with size and you're like, 'I really don't know!' The talk show legend wasn't called out at the time, but she did face widespread criticism when the clip resurfaced in 2021.

For most authors, getting selected for "The Oprah Winfrey Show" book club is the stuff of dreams. But back in 2004, Jonathan Franzen treated the honor like an affront to his craft. On learning that the talk show icon had chosen "The Corrections" for an upcoming episode, the author told NPR expressed concerns that he'd be misunderstood by such a populist show, arguing, "I feel like I'm solidly in the high-art literary tradition."

Soon after, Franzen questioned Winfrey's general taste in a chat with Powell's bookstore (via The New York Times): "She's picked some good books, but she's picked enough schmaltzy, one-dimensional ones that I cringe, myself." Of course, the ungrateful writer soon found out that revenge is a dish best served as an ice-cold retraction.

On learning about his snobbery, Winfrey issued a public statement (via Vox) that read, "Jonathan Franzen will not be on 'The Oprah Winfrey' show because he is seemingly uncomfortable and conflicted about being chosen as a book club selection. It is never my intention to make anyone uncomfortable or cause anyone conflict. We have decided to skip the dinner and we're moving on to the next book." Franzen, the first ever writer Winfrey had disinvited, later apologized to the billionaire, and in 2010, she selected his novel "Freedom" as a book club pick. This time around, the author kept schtum.

Ludacris was left ruing the day he agreed to appear on "The Oprah Winfrey Show" after its host essentially treated him like a naughty schoolboy. The rapper had joined several other castmates from the Oscar-winning "Crash" on the 2005 episode. But instead of discussing his acting abilities, Winfrey was more interested in castigating him for his lyrical flow.

Winfrey, who's famously not a fan of the hip-hop genre, took Ludacris to task for both his fondness for the N-word and the kind of rhymes that could be seen as misogynistic. The "Area Codes" hitmaker later told GQ that the aired conversation was more than a little one-sided: "She edited out a lot of my comments while keeping her own in. 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."

And Winfrey's schooling didn't end once the cameras stopped rolling, as Ludacris explained: "After the taping, she pulled me into a room and we had a five-minute conversation. What I got was that by having rappers on her show, she feels like she is empowering them." As with many of her celebrity feuds, Winfrey has since patched things up with the man born Christopher Brian Bridges.

Cindy Crawford appeared on "The Oprah Winfrey Show" nearly a dozen times during its decade-spanning run. But the "Fair Game" star doesn't appear to have forgiven its host for how she was treated on her debut.

During the opening episode of the Apple TV+ documentary "The Super Models" (via ET), Crawford recalls how uncomfortable she felt when she first met Winfrey in 1986. The fashion icon, aged just 20 at the time, was appearing alongside Elite Modeling Agency's John Casablancas. And she was left feeling like a child when the talk show legend completely ignored her and instead asked her rep if she always had such a body. 

And things only got worse, as Crawford explained, "When you look at it through today's eyes, Oprah's like, 'Stand up and show me your body. Show us why you're worthy of being here.' In the moment I didn't recognize it, and watching it back I was like, 'Oh, my gosh. That was so not okay, really.' Especially from Oprah." Winfrey was later defended by longtime friend Gayle King, who told ET, "It's not Oprah's thing to humiliate or make anybody feel badly." Eventually, the star deleted the clip from her YouTube channel. 

It turns out that Oprah Winfrey can sometimes stick her oar in when it's most definitely not wanted. In 2010, she asked Mo'Nique for her permission to record an episode of her self-titled chat show featuring the brother who'd molested the "Precious" star as a child. The Academy Award winner did give her blessing but was still left astounded when she tuned in to see various other family members also being interviewed.

Mo'Nique claimed to The Hollywood Reporter that she'd specifically told Winfrey beforehand about the strained relationship she had with her mom, in particular: "We weren't even speaking. Then I see the show and I can tell that my mother is trying to make a dollar. I know my family." She reportedly then tried to call the billionaire out on her sneakiness, but none of her calls were returned.

The comedian finally got to confront Winfrey at an Oscars party four years later, where the latter pleaded ignorance. Mo'Nique recalled hearing, "I'm going to look into your mother and father being on the show, because I didn't know anything about that ... If I've done anything to offend you, I apologize.'" But this wasn't enough to placate the wounded star who believed that Winfrey still wasn't telling the whole story.

Oprah Winfrey was accused of being heartless by her own stepmother after being "kicked out" of the five-bedroom south Nashville home she'd shared with the star's father for 14 years. Indeed, in 2014, former high school vice-principal Barbara Winfrey told Daily Mail that her life had been deliberately ruined by the talk show legend following a bitter divorce with Vernon Winfrey.

"Oprah's a billionaire three times over, her help live better than this," Barbara pointed out, adding, "She said publicly that she offered to sell the house and give me the proceeds, but that's a lie, she never said that.
 Oprah owns property all over the world so there is no reason to sell this house other than to spite me, it's a personal vendetta.'"

Legal papers obtained by the publication claim that Oprah was involved in a conspiracy to separate her father and stepmother, and essentially make the latter homeless. "What she has done is nothing short of evil, but she doesn't scare me, her actions cause me to disrespect her," Barbara stated.

In 1988, Oprah Winfrey bagged what she no doubt expected to be one of the juiciest celebrity interviews she'd ever conduct. After all, screen legend Elizabeth Taylor had seen and done it all during a decade-spanning Hollywood career in which she'd also walked down the aisle on no fewer than eight occasions (and twice to the same man).

However, the expected tell-all never came to fruition. In fact, the "Cleopatra" star barely said a word during her chat with Winfrey. And it didn't help matters, either, that the talk show host reneged on her promise to avoid the subject of Taylor's eventful romantic life. "None of your business," the Hollywood icon fired back (via The New Yorker) after one particularly intrusive question.

After receiving little more than one-word answers, a clearly frustrated Winfrey then mocked the extremely reticent Taylor with the sarcastic remark (via Oprah), "You're so revealing — you just tell everything! I declare, you've got to stop talking so much, Ms. Taylor." The Academy Award winner obviously didn't appreciate the quip, later remarking that her meeting with Winfrey spawned "the worst interview of my life."