20 Of Oprah’s Most Awkward Interviews Ever

Oprah’s televised talk with Prince Harry and Meghan Markle reminded us all just what a class act she is. But not every interview conducted by the talk show legend has gone so smoothly. From inappropriate jokes to interrogating fans, here’s a look at 20 times Lady O’s chats made us want to hide behind – rather than jump up and down upon – our sofas.

20. Oprah calls out Barbra Streisand’s diva demands

Barbra Streisand sure lived up to her diva reputation in 2003 when she paid a visit to Harpo Studios. The Yentl star famously rocked up in an all-ivory outfit that matched the color of her lapdog. And the singer even insisted that the microphone she used to perform a musical number be spray-painted to complete the uniform look.

Perhaps to Streisand’s surprise, Oprah let audiences know about this bizarre demand. The “Woman in Love” singer then defended herself, responding, “I like simplicity and monochromatic frame. So I thought, just look, if the mic melts in my sweater… In other words, it just makes the focus on the song.” That was Lady O told.

ADVERTISEMENT

19. Oprah describes James Frey as a “false person”

James Frey found out the hard way that you cross Oprah at your peril when he accepted an invitation to appear on her show in 2006. The author’s autobiography A Million Little Pieces had previously been selected for the host’s prestigious Book Club. But just three months after it shot to the top of the bestseller’s list, reports emerged that Frey had told several porkies about his harrowing life story.

It’s fair to say that Oprah wasn’t happy about inadvertently recommending someone she described as a “false person.” She told Frey, “I feel that you conned us all. Do you?” The chat show legend later said sorry to the writer for her character assassination. In fact, she asked him back to Harpo Studios in 2011 where she acknowledged that the book, fabricated in parts though it may have been, had still inspired those struggling with addiction problems.

ADVERTISEMENT

18. Oprah doesn’t think much of Anna Ginsberg’s cooking

After winning $1 million in a national culinary contest, amateur chef Anna Ginsberg was invited on to The Oprah Winfrey Show to further showcase her skills. But the host didn’t appear to be a fan of her take on spinach-stuffed chicken. When asked for her verdict, Oprah replied, “I do like it. I like it very much.” Her expression told a different story, though. To make matters worse, the talk show legend even asked for some seasonings.

ADVERTISEMENT

Oprah later explained this bit of shade throwing when the clip later resurfaced on social media. She wrote on Instagram, “So I was having a moment of trying to decide, ‘Do I want her to have a great time, what is my real moment of truth?’ Because the truth, for me, was that I am used to having salt and pepper on my chicken. That’s just the truth. That’s what I was thinking, ‘This chicken needs some salt and pepper!’”

ADVERTISEMENT

17. The lawyer who talked about his book 29 times

So who does Oprah herself consider the all-time worst interviewee? Well, she didn’t exactly name names when asked the juicy question on Harry Connick Jr.’s eponymous chat show in 2018. But Lady O no doubt got some fans trawling through past episodes to find the shameless mystery lawyer who she referenced.

ADVERTISEMENT

Oprah recalled how this master of self-promotion referred to his new book no fewer than 29 times. She explained, “Every sentence started. ‘In my book, in my book, and if you buy my book,’ and so finally, around the third segment, I said, ‘We all know the name of the book. Audience, tell him the name of the book… So you don’t have to say the name of the book anymore.’”

ADVERTISEMENT

16. Brad Pitt gets interrogated by a fan

Oprah no doubt ended up regretting inviting viewers to take on the interviewer role when Brad Pitt turned up to her set in 2008. While promoting The Curious Case of Benjamin Button alongside Cate Blanchett, the Oscar-winner was asked to field questions from fans through the method of Skype. And one particularly nosy admirer certainly made the most of her opportunity.

ADVERTISEMENT

A woman named Christina immediately made Pitt squirm when she started discussing the star’s relationship with Angelina Jolie. The actor responded, “If you have a partner, it’s great fun, it’s a great thing to go do together. It becomes personal and special in its own right. I’d rather just leave it at that.” Pitt’s request for privacy fell on deaf ears, though, and Christina continued to quiz him about other personal matters, including his various tattoos.

ADVERTISEMENT

15. Lance Armstrong bombs with an inappropriate joke

Oprah certainly wasn’t impressed with Lance Armstrong’s attempt at humor during their revealing chat in 2013. The cyclist was being interviewed in the wake of the performance-enhancing drug scandal that destroyed both his reputation and his career. But Armstrong didn’t appear to be particularly contrite when questioned about his behavior toward someone who’d called him out, Betsy Andreu.

ADVERTISEMENT

While recalling a chat he’d had with the wife of his ex-teammate Frankie Andreu, Armstrong quipped, “I said, ‘Listen, I called you crazy. I called you a *****. I called you all these things, but I never called you fat.’” The Tour de France winner was obviously expecting Oprah to laugh at that final line. But instead the talk show veteran offered nothing but a stone-cold glare.

ADVERTISEMENT

14. Oprah puts Mackenzie Phillips on the spot

Writing your troubling life story in the privacy of your own home is one thing. Reading it aloud in front of millions of viewers is another thing entirely. Little wonder, then, that Mackenzie Phillips was caught off-guard when she was asked to narrate a passage from her autobiography, High on Arrival, during an appearance on The Oprah Winfrey Show in 2009.

ADVERTISEMENT

Phillips responded, “Wow. This wasn’t exactly how I envisioned this going down, but that’s all right.” The daughter of the singer from The Mamas & the Papas revealed seven years later on Where Are They Now that, actually, it wasn’t all right. She told the show, aired on the Oprah Winfrey Network (OWN), “I felt, here I was with this huge piece of information that maybe wasn’t even fit for public consumption… In retrospect there was some due diligence I missed doing, like preparing myself for losing my family.”

ADVERTISEMENT

13. Oprah responds strangely to Elizabeth Gilbert’s grief

Elizabeth Gilbert’s appearance on Super Soul Conversations in 2019 wasn’t exactly light-hearted in tone. On the promotional trail for her latest book City of Girls, the author opened up about the death of her girlfriend Rayya Elias. Gilbert told the chat show legend how she still leaves voice notes and writes messages to her late partner. Yet the interviewer’s response to this outpouring of grief was deemed as inappropriate by some.

ADVERTISEMENT

After hearing Gilbert discuss her coping mechanisms, Oprah said, “That’s some woo-woo stuff, I got to tell ya. That is some woooooo-woooooo!” This slightly baffling response surprised some fans of the typically articulate talk show host. Toronto writer Kate Carraway commented, “If Oprah Winfrey can’t take in the whole of someone else’s – awkward, maybe freaky – grieving process, what hope is there for the rest of us to understand, or be understood?”

ADVERTISEMENT

12. Oprah gets too nosy with Elizabeth Taylor

Even Lady O herself admits that this 1998 interview with Elizabeth Taylor is “still painful to watch.” But you could argue that the chat show host didn’t make things easy for herself. Taylor had stated beforehand that the subject of her love life was strictly off-limits. But Oprah ignored this request entirely.

ADVERTISEMENT

After being asked a question she considered to be particularly invasive, Taylor replied, “None of your business.” Oprah later sarcastically remarked, “You’re so revealing – you just tell everything! I declare, you’ve got to stop talking so much, Ms. Taylor.” You might be surprised to learn that despite this awkward encounter, the Cleopatra star returned to the Harpo set several times.

ADVERTISEMENT

11. Oprah questions 50 Cent’s choice of pet name

Rapper 50 Cent wasn’t exactly Lady O’s biggest fan in the mid-2000s. While chatting with the Associated Press, Fiddy argued that the chat show host was prejudiced against modern musicians such as himself and that her show catered only to “older white women.” Oh, and he named his dog Oprah, something which didn’t go appreciated by the national treasure, that’s for sure.

ADVERTISEMENT

During his 2012 appearance on Oprah’s Next Chapter, the rapper was inevitably forced to address his choice of pet name. So 50 Cent explained, “At the time, I was just looking at the situation and I saw I was developing negative feelings for someone who doesn’t even know me. And I gave it to the dog, cause I was excited about the dog at the time.”

ADVERTISEMENT

10. Oprah’s unsuccessful therapy session with Terry McMillan

You’d have needed a particularly sharp knife to cut the atmosphere when Terry McMillan graced The Oprah Winfrey Show with her former husband in 2005. The How Stella Got Her Groove Back author had divorced Jonathan Plummer after he revealed that he was a gay man. And the pair spent most of their time on set at daggers drawn.

ADVERTISEMENT

After McMillan discussed the sense of shock she felt on learning of her husband’s true sexuality, Oprah queried whether the one-time couple could ever have a platonic relationship. While Plummer seemed keen, McMillan wasn’t even entertaining the idea. She replied, “No we’re not. We’re not going to be kicking it.”

ADVERTISEMENT

9. Teenage Mutant Ninja Turtles scar fans for life

Oprah invited a whole host of kids to sit in the audience for her interview with the live-action version of Teenage Mutant Ninja Turtles in 1990. And she may well have ended up traumatizing them for life. And that’s because her interview with the heroes in a half-shell, who were also joined by characters Shredder and April O’Neill, soon turned very awkward indeed.

ADVERTISEMENT

Firstly, the pizza-obsessed reptiles start stroking O’Neill’s chin when she admits how attractive she finds them. Then things get even weirder when Raphael and Michelangelo begin talking about “interspecies relationships.” When the cameras cut to the pained young faces in the studio, it appears as though the interview has destroyed every TMNT fan’s childhood.

ADVERTISEMENT

8. Oprah tries to wipe off Drew Brees’ birthmark

Everybody’s favorite chat show host no doubt wanted the ground to swallow her up when she found out exactly why Drew Brees had a red mark on his face. After excitedly greeting the star quarterback on her show in 2010, the host remarked, “Who just kissed you?” Winfrey believed that someone had left a lipstick smudge on Brees’ cheek and even tried to wipe it off. This tactic didn’t exactly work as the blemish in question was a birthmark.

ADVERTISEMENT

To his credit, Brees brushed aside the embarrassing gaffe off at the time. In memoir Coming Back Stronger the NFL star revealed he had no shame about his distinctive feature. He wrote, “Instead of seeing it as a bad thing, I chose to see it as something that made me unique and special. It set me apart from everyone else… Now it’s just a part of who I am.”

ADVERTISEMENT

7. Ludacris felt ostracized by Oprah

In 2005 Ludacris joined several of his Crash co-stars on The Oprah Winfrey Show to promote the future Best Picture Oscar-winner. But the rapper later claimed that he wasn’t treated with as much respect as his fellow actors by the talk show host. In fact, the “Area Codes” hitmaker argued that most of his remarks were cut from the final edit. And he believes that Oprah’s disdain for hip-hop was to blame.

ADVERTISEMENT

Ludacris told GQ magazine in 2006, “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. It was like being at someone’s house who doesn’t really want you there. It was already uncomfortable.”

ADVERTISEMENT

6. Oprah questions the Olsen Twins on their size

You could say that Oprah didn’t cover herself in glory in 2004 when she invited Mary-Kate and Ashley Olsen on to the Harpo set. Then only 17 at the time, the former was questioned about rumors of an eating disorder. And just as the former Full House star was giving her answer, Oprah rudely interrupted to ask an inappropriate question.

ADVERTISEMENT

Much to the twins’ discomfort, Oprah asked, “What size are you, by the way?” After Ashley replied that they were “petite,” the host remarked, “Oh, that’s so interesting. That is so interesting, I’m obsessed with size and you’re like, ‘I really don’t know.’” Lady O’s questionable remarks went fairly unnoticed at the time but drew criticism when the interview found its way onto TikTok 17 years later.

ADVERTISEMENT

5. Oprah grills friend Jay Leno

Oprah could never be accused of giving her friends special treatment. In 2010 she sat down with Jay Leno, a longtime pal, in the wake of his talk show drama with Conan O’Brien. And the media mogul soon let her guest know that she didn’t approve of him ousting the red-haired comedian from his position on The Tonight Show.

ADVERTISEMENT

“Did you ever ask yourself, ‘Am I being selfish?’” was just one of the tough questions Oprah posed to Leno during the course of their interview. She also asked him, “Were you embarrassed about how all of this transpired?” and “Do you think celebrities will still come on your show?” The look on Leno’s face suggested he hadn’t been expecting such a tough ride.

ADVERTISEMENT

4. Oprah questions Whitney Houston’s vocal care

In 2009 Whitney Houston joined Oprah for what would sadly prove to be one of her final in-depth interviews. Just three years before her tragic death, The Bodyguard star opened up about her issues with substance abuse and her marriage to Bobby Brown. The talk show host appeared sympathetic throughout but couldn’t resist from asking one question which seemed to raise Houston’s hackles.

ADVERTISEMENT

The awkward moment occurred when Oprah referred to a report about how disgusted fans were that Houston had failed to look after her “national treasure” vocal range. Visibly taken aback, the singer could only offer “Wow,” in response. Houston’s voice was also called into question during a breathless interview with Good Morning America shortly after. The “So Emotional” hitmaker blamed her chat with Lady O for wearing her out.

ADVERTISEMENT

3. Oprah asks Michael Jackson if he’s a virgin

One of the most memorable interviews of Oprah’s career came in 1993 when she visited the Neverland Ranch for a candid talk with Michael Jackson. And she soon proved once again that she wasn’t afraid to pose the questions others wouldn’t dare. As well as grilling the King of Pop on his ever-changing skin tone, the chat show legend also asked whether he was a virgin.

ADVERTISEMENT

As you would expect, Jackson didn’t take too kindly to such a query, replying, “How can you ask me that? I’m a gentleman.” Unfortunately for Oprah, Elizabeth Taylor, the woman she’d later describe as one of her hardest interviewees, soon interrupted proceedings. And the Hollywood legend ensured that her BFF didn’t have to answer any more tough questions.

ADVERTISEMENT

2. Oprah is fat-shamed by Joan Rivers

You could say that Oprah endured a baptism of fire when she made her national TV debut in 1985 on The Tonight Show. The star had prepared for every possible question she could think of, but she was understandably thrown when Joan Rivers asked, “So how’d you gain the weight?” In her Food, Health and Happiness book, Oprah recalled how she felt at the time, writing, “The studio started spinning. The word ‘fat’ reverberated in my brain.”

ADVERTISEMENT

Oprah went on to add, “Joan sat behind Johnny’s big wooden desk, telling me that she didn’t want to hear my excuses and that I shouldn’t have let this happen… She 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.” According to the National Enquirer newspaper, Rivers continued to hold a grudge against Lady O, reportedly describing her as “completely opportunistic.”

ADVERTISEMENT

1. Tom Cruise’s sofa jumping

Tom Cruise’s 2005 interview with Oprah should have been a relatively straightforward one to help promote his latest movie, War of the Worlds. Instead, it turned into a baffling display of public affection which has gone down in infamy. As you no doubt remember, when asked about his burgeoning romance with Katie Holmes, Cruise didn’t just gush about the Dawson’s Creek star. He leapt onto the sofa like an excitable child.

ADVERTISEMENT

Oprah could only remark, “He’s gone, he’s gone, the boy is gone,” during Cruise’s bizarre fist-pumping, couch-jumping explosion. Although those in the studio cheered in support, everyone watching at home was left utterly bemused. As website The Ringer noted more than a decade later, “Instead of making people think he was a romantic, Cruise just made people think he was weird.”

ADVERTISEMENT
ADVERTISEMENT
ADVERTISEMENT