When Mary-Kate and Ashley Olsen attended the Oprah Winfrey Show, the then 18-year-olds expressed their concerns about people speculating about them having an eating disorder.

“I know a new rumor [that’s] recently surfaced has really upset you, right?” the TV host told the sisters. “You know, the one about eating.”

“It’s either ‘you’re too fat’ or ‘you’re too skinny.’ People are going to write what they want. We try not to read the good or the bad,” the twin sisters replied.

For some reason, Oprah thought, “What size are you, by the way?” was a relevant follow-up question. 

The controversial clip was unearthed in 2021, with many people pointing out that the question made the sisters feel uneasy.

In 1986, Oprah asked Cindy Crawford to stand up so everyone could look at her body. She even suggested that Elite Model Management Founder John Casablancas had “groomed her.”

Crawford called out the talk-show host for objectifying her body on Apple TV’s docuseries, The Super Models, which premiered 37 years after the infamous interview.

"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,'" the model said. "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.”

The interview was removed from Oprah’s YouTube channel following social media backlash.

Another question that didn’t age well is whether or not someone is a virgin.

But that’s exactly what Oprah asked during a live, hour-long television special back in February 1993.

The interview served to improve the “Smooth Criminal” singer’s image in a context in which he faced allegations of sleeping in an oxygen chamber and having bought the Elephant Man’s remains.

Still, it came with a cost: Jackson couldn’t avoid the interviewer’s interest in his sex life. 

“How could you ask me that question?” he said in response. “It’s something that’s private.”

"Are you worried about being typecast?" Oprah asked Lane about his role in the movie The Birdcage, in which he stars alongside Robin Williams and plays the main attraction of a drag club in South Beach.

Reflecting on the awkward question, Lane said “I don't think Oprah was trying to out me, but I said to Robin beforehand: 'I'm not prepared. I'm so scared of going out there and talking to Oprah. I'm not prepared to discuss that I'm gay on national television, I'm not ready.’”

Robin responded by saying “Oh, it's alright, don't worry about it, we don't have to talk about it, we won't talk about it.”

Sadly, he was wrong.

Lane, 67, publicly came out in 1999, three years after the interview.

Asking a sexual question to a man dressed in a Teenage Mutant Ninja Turtles costume is rather bizarre in itself, and even more so with children present in the audience.

You can probably guess that their parents never took them to the studio again.

Mistaking an interviewee's birthmark for a lipstick smudge is one thing. Trying to wipe it off on national television is another.

While the ex-NFL star laughed about Oprah's misstep in 2010, he later revealed that he suffered bullying during his childhood as a consequence of the mark on his cheek and he used to be ashamed of it.

Fortunately, things have changed since. In his book, he shared that he has learned to appreciate his mark as a feature that makes him unique, which is why he’d never have it removed.

“It's just a part of who I am. I wouldn't  consider cutting off my arm; neither would I cut off my birthmark,” he wrote.

It’s no secret that many celebrities have gone under the knife to feel more confident in their own skin.

Still, not everyone feels comfortable with sharing their experiences in the surgery room.

When Oprah asked Dolly Parton how she maintained such a young image, the country star answered, “I don’t know. I’m a cartoon, so I just look the same all the time.”

The talk show host insisted on the idea of plastic surgery, making Dolly laugh uncomfortably and confirm that she had gotten cosmetic procedures done in the past.

After the video resurfaced, people accused the host of trying to humiliate Dolly for her personal choices regarding her appearance.

It’s not uncommon for celebrities to be guarded about their dating life, especially in highly publicized interviews. This didn’t exactly sit well with Oprah.

“You’re so revealing. You just tell everything. You gotta stop talking so much,” the host sarcastically teased Elizabeth Taylor after she refused to give details about her love life. 

Oprah isn’t too proud of this moment, especially considering that the actress had asked her to avoid questions about her relationships prior to the interview.

“It’s still painful to watch. For many reasons—including my bad hair,” the talk show host said of the cringy 1988 interview.

To this day, Oprah regrets asking Sally Field whether her partner, actor Burt Reynolds, slept “with his toupée on.”

"I even say now, I cringe to even think that I asked that question. But I asked it because the producers are like, 'You have to ask, you have to ask, you have to ask. That's what everybody wants to know’,” Oprah said in 2021 about the interview.

In retrospect, she understands why Field went cold on her.

“I deserved it, because that is such an inappropriate question.”

Longtime fan Christina called Oprah’s show in 2008 to ask Brad Pitt a very important question: what was the meaning behind his iceman tattoo?

“I know you’ve got one on your tummy. Don’t make me go there,” she said on a video call.

If things weren’t already awkward enough, Oprah asked the Oscar winner to show his tattoo in front of everyone.

In 2003, the songstress was proud to rock her white turtleneck and walk around the Oprah Winfrey studio carrying her matching white dog, Sammie, and white microphone.

The host wasn’t a fan of her all-white-everything look. “I just want to say… I own this studio. I’ve been here I don’t know how many years, and I’ve never seen a white microphone,” she told her guest.

Streisand corrected her by saying it was actually “off-white,” and that she enjoyed “monochromatic frames.”

“So you had the mic sprayed?” the host continued.

“That’s right,” Streisand said, concluding the tense interaction.