10 Uncomfortable Or Awkward Interview Moments From "Oprah"

Being a talk show host requires great interview skills. However, among the hundreds or even thousands of interviews they conduct, many hosts occasionally ask a question that they probably shouldn't have.


The past few years, viewers have been reflecting on these cringey or uncomfortable moments from hosts like David Letterman, Ellen DeGeneres, and Jimmy Fallon. Sometimes, even the celebs themselves chime in. Recently, Cindy Crawford reflected on her experience on The Oprah Winfrey Show, and it had a lot of fans side-eyeing other moments from the long-running series.

closeup of young Cindy Crawford
WLS-TV Chicago / Via youtube.com

Here are 10 awkward, cringey, or uncomfortable moments from The Oprah Winfrey Show:

Warning: Some entries mention eating disorders.

1.When Oprah interviewed Cindy Crawford and Elite Model Management founder John Casablancas in 1986, she had the young model stand up so the audience could see her body.

Screenshots of Cindy on Oprah's show
WLS-TV Chicago / Via youtube.com

Here's the full clip, with this part starting at the 0:53 mark:

Reflecting on the encounter 37 years later on Apple TV+'s The Super Models, Cindy said, "I was like the chattel or a child, be seen and not heard."

Closeup of Cindy Crawford
Apple TV+

"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,'" she 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."

2.When Mary-Kate and Ashley appeared on the show in 2004, Oprah brought up rumors that they had eating disorders. After the 18-year-olds told her they tried "not to read the good or the bad" things people wrote about them, she asked what clothing sizes they wore.

Closeup of the Olsen twins
Harpo Productions

Here's the full clip:

Harpo Productions / Via tiktok.com

3.When Robin Williams and Nathan Lane did a joint interview to promote The Birdcage in 1996, Oprah brought up potential rumors about Nathan's sexuality since he played an openly gay character in the film. At the time, he wasn't ready to discuss his sexuality publicly, so Robin quickly changed the topic by making a joke.

"Girl, you changed just in the middle of that sentence!"
Harpo Productions

On a 2023 episode of Sunday Sitdown with Willie Geist, Nathan 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.' And [Robin] said, 'Oh, it's alright, don't worry about it, we don't have to talk about it, we won't talk about it.'"

Closeup of Nathan Lane
NBC / Via youtube.com

He then said that Robin "sort of swoops in and diverts Oprah and goes off on a tangent and protects [him] because he was a saint."

Watch the full clips from both interviews in this compilation below:

Harpo Productions / NBC / Via tiktok.com

4.When NFL quarterback Drew Brees visited her show in 2010, Oprah mistakenly thought his birthmark was a woman's lipstick print, so she tried to wipe it off.

"There's a big 'ol kiss right there."

Here's the full clip:

5.In 1988, Elizabeth Taylor playfully shut down Oprah's attempts to get her to address dating rumors, and Oprah teased her about her refusal to give a straight answer.

Elizabeth Taylor and Oprah
WLS-TV Chicago / Via youtube.com

Watch the full clip below:

Reflecting on the interview — which she called her "worst" — years later, Oprah told Oprah.com, "It's still painful to watch. For many reasons — including my bad hair."

Closeup of Oprah
WLS-TV Chicago / Via youtube.com

Explaining that, before the interview, the actor asked her to stay away from questions about her relationships, Oprah said, "That's kind of hard to do when you're Elizabeth Taylor, and you've been married seven times... To her credit, she later apologized to me."

6.In 1993, Oprah asked Michael Jackson if he was a virgin, then pressured him to answer when he tried to skirt around it.

Closeup of Michael Jackson
Harpo Productions / Via youtube.com
"So you're not going to answer it?"
Harpo Productions / Via youtube.com

Watch the full clip below:

7.When the Teenage Mutant Ninja Turtles appeared on her show in 1990, Oprah asked them a relationship question about their human friend April in front of an audience filled with children.

"Do you sometimes wish that April was a turtle?"
Harpo Productions / Via youtube.com

The children in the audience were seemingly horrified.

Closeup of kids in the audience
Harpo Productions / Via youtube.com

Here's the full clip:

8.In 2003, Oprah pressured Dolly Parton to reveal what kind of cosmetic surgery she'd had done.

"some tucks and pulls and sucks."
Harpo Productions / Via youtube.com

Here's the full clip:

9.When Brad Pitt and Cate Blanchett did a joint interview in 2008, a viewer called in to ask about the meaning behind his tattoos.

"No, I won't, but, uh"

When Brad declined to talk about them, Oprah asked the fan for more details.

"What are you talking about?"

Watch the full clip below:

10.And finally, on a 2021 episode of Literally! With Rob Lowe, Oprah said that she made a "big mistake" when she asked Sally Field, "Does Burt [Reynolds, Sally's then-partner] sleep with his toupee on?" Then, the actor "went cold."

Closeup of Sally Field and Burt Reynolds
Ron Galella / Ron Galella Collection via Getty Images, Team Coco Podcasts / Via youtube.com

Oprah said, "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.' ... She shut down, and I could not get in again."