11 Times Oprah Made People Uncomfortable

This feature includes references to eating disorders, drug misuse, addiction, child abuse, and sexual assault. 

One of the most famous women in the world, Oprah Winfrey has been in the media for decades. The star hosted "The Oprah Winfrey Show" for 25 years, and during that time she became known for interviewing everyone from eager actors in new relationships to a beleaguered member of the royal family. Oprah was seemingly willing to interview anyone and everyone — the crazier the story, the better.

With that territory comes the occasional uncomfortable interview. Though most of the time Oprah has kept her cool, sometimes her line of questioning has seemingly crossed a line with her subject. Subsequently, there have been a handful of interviews where her guest appeared anxious and uneasy, making the segments disconcerting to watch. Since she's so famous, Oprah has even managed to make some people feel uncomfortable even without inviting them on her show. 

From actors and singers to public figures and athletes, Oprah has put someone on edge in every field of entertainment. Get in the hot seat as we dig into some of those memorable interviews and feuds.

We've all erred in our careers — even media mogul, Oprah Winfrey. On Rob Lowe's podcast, "Literally! With Rob Lowe," she shared one of her biggest missteps in her journalism career, during an interview with Sally Field. The acclaimed actor is professionally known for her performances in films like "Steel Magnolias," "Forrest Gump," and "Mrs. Doubtfire," and personally known for her bygone relationship with Burt Reynolds.

Although the interview was going well, it quickly went awry. "This is when I was younger, and I was not, like, living from the point of view of the surrogate," Oprah said. "... I did feel a responsibility to have to ask the questions that the viewer wanted, and Sally Field was on. My big mistake, I asked her, 'Does Burt sleep with his toupee on?' ... I cringe to even think that I asked that question ... I asked it, and she went cold on me."

It's safe to assume it was the question Field took issue with, not the topic, as she's been candid about her relationship with Reynolds in other interviews. "He was not someone I could be around. He was just not good for me in any way," she told Variety in 2022. Field added that she wasn't anywhere near as important to the actor as he wanted to believe. "He just wanted to have the thing he didn't have," she shared. "I just didn't want to deal with that."

For Jay Leno, the late aughts were defined by multiple major career shifts. In 2009, the legendary comic hosted his last episode of "The Tonight Show," ending his decades-long tenure. Replacing Leno was Conan O'Brien, a choice that surprised many. What was perhaps even more surprising was that after a season of low ratings, O'Brien left "The Tonight Show," and Leno returned as his replacement.

After the controversy, the late-night host sat down with Oprah Winfrey to discuss his feelings about the ordeal. Like her, Leno is used to asking questions rather than answering them, and his unease about the position was apparent. "Did you ever ask yourself, 'Well, am I being selfish?'" Oprah asked. "I don't think so," Leno answered. "I like the job. I like all that goes with it. I fight for the people that work here. I fight to keep the jobs here. Is that selfish?" he continued.

Bringing up the rumors that Leno had sabotaged O'Brien's show to steal it back from him, Oprah made her position clear. "I'm really surprised that so many people are against you because I think that people don't understand the way television works," she said in defense of her friend. Leno added that he prefers to work for someone else, not own his own show, to which Oprah said, "Owning the show's pretty good, too."

In the '90s and early 2000s, few young stars were as popular as Mary-Kate Olsen and Ashley Olsen. The twins' career began when they were infants, with the two sharing the role of Michelle Tanner on "Full House," for the sitcom's entire eight seasons. In 2004, the two appeared on "The Oprah Winfrey Show" for the first time ever, which the host excitedly shared at its onset. However, the interview took an uncomfortable turn near the end, when the host clumsily addressed speculation that Mary-Kate had an eating disorder. "There's a new rumor recently surfaced [that] has really upset you, right?" Oprah asked the Olsen twins. "You know, the one about eating."

Ashley answered by stating, "People are gonna write what they want to write. We try not to read the good or the bad because it just kind of comes with the territory ... Either you're too fat or too skinny." She was then interrupted by Oprah asking, "What size are you, by the way?" leaving both sisters stunned. "Size?" Ashley clarified with wide eyes, seemingly shocked she'd be asked such a question, before quipping, "I'm really short." Mishearing her response, Oprah groaned, "You're not sure? Oh, that's so interesting."

Just months later, the New York Post reported that Mary-Kate was being treated for an eating disorder at a private health facility. Four years later, while refusing to confirm or deny the report, she told Elle, "Everybody is going to go through hard times. It's a part of life."

If you need help with an eating disorder, or know someone who is, help is available. Visit the National Eating Disorders Association website or contact NEDA's Live Helpline at 1-800-931-2237. You can also receive 24/7 Crisis Support via text (send NEDA to 741-741).

Elizabeth Taylor is one of the world's greatest and most famous actors of all time. With two Oscars and seven husbands, Taylor was as great an artist as she was an intriguing public figure. It's no wonder journalists like Oprah Winfrey were clamoring for an opportunity to interview her. However, the interview didn't turn out to be quite what Oprah, or perhaps anyone, anticipated.

Prior to their meeting, Taylor told the host she wouldn't answer any questions about her romantic history. Oprah's response was, "That's kind of hard to do when you're Elizabeth Taylor and you've been married seven times." When she attempted to broach the off-limits topic, Taylor quipped, "None of your business." Oprah tried to cut the tension by joking, "You're so revealing — you just tell everything! I declare, you've got to stop talking so much, Ms. Taylor." It didn't work.

Upon review, the interview was as bad for Oprah as it was for viewers. As she shared on Oprah.com, "It's still painful to watch. For many reasons — including my bad hair." The interviewer excused some of the awkward discomforts of the exchange by noting that Taylor was in physical pain with her back and hip during the interview. "To her credit, she later apologized to me," Oprah added.

Lance Armstrong is best known for his cycling career, having won the Tour De France an unprecedented seven times in a row at his peak. But it was later discovered that he had been using performance-enhancing drugs, and he was subsequently stripped of all his Tour titles. In 2013, Armstrong sat down for an episode of "Oprah's Next Chapter," to confess his transgressions to her and the world.

Visibly nervous, Armstrong entered the conversation with a vow to be completely honest in his answers. Oprah asked the cyclist a series of yes or no questions relating to the types of performance-enhancing drugs he used to achieve his sports victories. He answered yes to a number of difficult questions such as, "Did you ever blood dope or use blood transfusions to enhance your cycling performance?" and, "Did you ever use any other banned substances, like testosterone, cortisone, or human growth hormone?" He also asserted his belief that he couldn't have enjoyed his winning streak without the enhancement of such drugs. 

Six years after the interview, Armstrong appeared on "Today" to update those interested in his life post-scandal, as well as to reflect on his discussion with Oprah. "That interview came at an interesting time, and at a difficult time, and maybe in a lot of ways came too soon ... At that point in my life, I wasn't gonna be able to lie. I was gonna have to be honest," he said of the interview.

Many people lie, but few people are confronted about their lies by Oprah Winfrey. In 2003, author James Frey's acclaimed memoir, "A Million Little Pieces," was published, about his personal experiences with addiction. Selecting the bestseller for her book club, she told her audience (via Los Angeles Times), "It's a gut-wrenching memoir that is raw and it's so real." Just a few years later, The Smoking Gun released a piece accusing Frey of lying about his story, prompting Oprah to invite him onto her show to discuss the accusations. "I don't know what is true, and I don't know what isn't," she began.

Frey was clearly uncomfortable during the interview. Feeling deceived, his interviewer was in an unusual state herself. "I was pretty defensive," she later reflected about the controversial chat. "I was defending my turf, and I was defending every single viewer who had bought that book." Oprah added that upon reflection, she lost her ability to interrogate her subject without judgment. "I've always tried to ... see [the interview subject] as a human being and look at them with some sense of compassion, and I did not do that [with] James Frey," she said.

In 2011, the two sat down for another conversation. This time it was revealed that Oprah had regretted the interview, and had called the writer years later to apologize for it. "We had a nice conversation, and I really appreciated it," Frey told her. 

NFL quarterback, Drew Brees is best known for his talent on the football field, even earning MVP after winning the 2010 Super Bowl. Upon his historic win, Brees didn't go to Disneyland. Instead, he visited "The Oprah Winfrey Show" to sit down with its eponymous host. But what should have been a standard segment, began with an uncomfortable moment that could've easily sent the entire interview awry. 

After both Brees and Oprah sat down, the host leaned over to her guest, wiped at his cheek, and asked, "All right, who just kissed you?" seemingly mistaking the mark on Brees's face for something that can be easily removed. As Brees has noted before, he has a birthmark on his right cheek, and he was visibly uneasy after Oprah took an unsolicited pass at his face.

Though Brees didn't address the moment publicly, he has shared how his birthmark affected him growing up. "Because of my birthmark ... I got all kinds of comments when I was a kid," he told CNN. "Wipe that whatever off your face ... people called me spot. Whatever. I think they were trying to be malicious," he added. He continued that he dealt with the teasing, but it eventually turned into a badge of honor. Speaking about how fans mark their own faces as an homage to him, he said, "I guess we come full circle from [bullying] ... because of the birthmark to people wanting to emulate that."

In 2005, to promote the movie "Crash," Oprah invited the cast of the Oscar-winning film and director Paul Haggis onto her show. While most of the film's stars like Don Cheadle, Sandra Bullock, Thandiwe Newton, Matt Dillon, and Terrance Howard seemed pleased to be invited, Ludacris was unhappy with the outcome of the interview. Particularly in how, as he saw it, the host took aim at his music. 

The rapper spoke about his distaste for Oprah's treatment of him in a later interview with GQ and accused her of having edited out many of his responses, in favor of her own. "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," he said. Discussing the issue further, he added that he wasn't originally even part of the ensemble interview, but was added in at the last minute. "Since I wasn't invited at first, it was like being at someone's house who doesn't really want you there. It was already uncomfortable," he lamented.

The star further suggested that the talk show host had a particular problem with rappers — an accusation she's previously denied. "I don't see why people like Chris Rock and Dave Chappelle ... it's okay for them to go on 'Oprah,'" he mused. "They speak the same language as I do, but they do it through comedy, so I guess that's acceptable to her."

Ludacris isn't the only rapper who's felt some ice from Oprah. 50 Cent, who ascended to incredible heights of fame thanks to his 2003 album "Get Rich or Die Tryin'" once told The Guardian that Oprah wasn't a fan of his. "She was completely against everything that was in my music. So she ain't never going to have me on that show ... So I just said: 'OK, if we can't be friends, then at least let's be enemies,'" he said. The rapper explained that he was eager to be interviewed by the TV show host to make his grandmother happy. However, Oprah allegedly resisted inviting 50 on her show because she objected to the violent and misogynistic aspects of his lyrics. 

Apparently, the two later became friends. Eventually, he and Oprah even enjoyed the chat he'd always dreamed of. "We finally met, and my grandmother and I went on the show," he told People. "That was an amazing moment for me." Still, the pair have apparently never discussed the more negative elements of his lyrics. Speaking to The Guardian, he defended his lyrics, stating, "The truth is, all things come from your experience. Like, I got shot nine times and I wrote music about it." 

He was later uncomfortable with Oprah again when she signed on to play a role in a documentary about one of the women who accused Russel Simmons of sexual abuse. Per XXL, 50 was placated when Oprah dropped out of the film in 2020.

Another rapper to find fault with Oprah is Ice Cube. In 2006, he griped to FHM (via ABC News) that the media mogul made him feel left out. "I've been involved in three projects pitched to her, but I've never been asked to participate," he shared. Though Cube rose to fame as part of the rap act, N.W.A., he is also known for his acting career, having starred in films like "Friday," "Ride Along," and "Are We There Yet?" as well as all their sequels. Cube noted that he's also never been asked to be interviewed by Oprah. "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?" he questioned. 

During a 2008 episode of "Conversations with Michael Eisner," the eponymous host grilled the rapper on what he thought Oprah's problem was with him. Pointing out that Cube wasn't invited to her prestigious Legends Ball in 2006, despite his production company seemingly being involved behind the scenes, Michael Eisner suggested there must have been some conflict between the two. "I don't know," he responded. "I haven't had a conversation with her ... I'm fine with that, I've gotten this far without Oprah, so, I'm not worried about it. [But] it would have been nice to show that my company did bring that show to America." As of 2022, Cube is still yet to be interviewed by her.

The 2009 Oscar-winning film, "Precious," featured Mo'Nique as an actor and Oprah Winfrey as an executive producer. During a conversation on FOX Soul in 2022, the star alleged that she felt pressured by the film's production team to campaign for an Oscar for her performance in the movie. As she saw it, this meant doing additional work to promote the movie, without compensation. Allegedly, as a result of this, Mo'Nique was called difficult – and she claimed that Oprah hardly rushed to her defense about it. "So now nobody's going to touch Mo'Nique because Oprah Winfrey said nothing," she stated. Thankfully, she still took home the Best Supporting Actress Oscar for her performance.

A year later, Oprah invited Mo'Nique's brother on her show to discuss the allegations that he had sexually abused his sister as a child. During an interview with Comedy Hype, the comedian revealed that after turning down an invite to join the episode, the host then asked for Mo'Nique's blessings before moving forward with it. Although Mo'Nique had respect for Oprah's considerate approach, her feelings soon changed once she saw adverts for the episode which revealed that her mom, dad, and other brother were also featured in the episode. She felt betrayed. "Had Oprah Winfrey said, I'm gonna have your mother [on],' I would've said, 'Shut it down. I don't want the world seeing how greedy my mother is.'" As of 2022, the actor and the interviewer haven't resolved their differences.

If you or someone you know may be the victim of child abuse, please contact the Childhelp National Child Abuse Hotline at 1-800-4-A-Child (1-800-422-4453) or contact their live chat services.

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).