“Did You Have To Groom Her?”: 11 Most Uncomfortable ‘Oprah’ Show Moments

Throughout the 25 seasons of hericonic show, Oprah Winfrey has sat with around 28,000 fascinating guests for open and honest interviews. Unfortunately, not every conversation went smoothly or turned out the way she had expected.Oprah—who has been dubbed the Queen of All Media—has made some regrettable choices in front of her live television audience, pushing her guests a little too far to clarify dating rumors or making intrusive questions about their cosmetic procedures.Here are a few uncomfortable interviews that produced some of the most talked-about episodes in television history.This post may includeaffiliate links.

Oprah—who has been dubbed the Queen of All Media—has made some regrettable choices in front of her live television audience, pushing her guests a little too far to clarify dating rumors or making intrusive questions about their cosmetic procedures.

Here are a few uncomfortable interviews that produced some of the most talked-about episodes in television history.

This post may includeaffiliate links.

When Mary-Kate And Ashley Appeared On The Show In 2004

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

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-longtelevision specialback in February 1993.The interview served to improve the “Smooth Criminal” singer’s image in a context in which he facedallegationsof 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.”

In 1993, Oprah Asked Michael Jackson If He Was A Virgin, Then Pressured Him To Answer When He Tried To Skirt Around It

When Robin Williams And Nathan Lane Did A Joint Interview To Promote The Birdcage In 1996

Asking asexual questionto 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.

When The Teenage Mutant Ninja Turtles Appeared On Her Show In 1990

Mistaking an interviewee’s birthmark for a lipstick smudge is one thing. Trying towipe it offon national television is another.While the ex-NFL star laughed about Oprah’s misstep in 2010, he laterrevealedthat 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.

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

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 staranswered, “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, peopleaccusedthe host of trying to humiliate Dolly for her personal choices regarding her appearance.

In 2003, Oprah Pressured Dolly Parton To Reveal What Kind Of Cosmetic Surgery She’d Had Done

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 sarcasticallyteasedElizabeth 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.

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