Making fun of a birthmark. Asking about a guest's dress size. Oprah
seriously made these celebs uncomfortable!
Everybody makes mistakes, including Oprah Winfrey. On Rob Lowe's podcast,
"Literally! With Rob Lowe," she shared one of the biggest missteps of her journalism career, which
happened 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 she is
personally known for her bygone relationship with Burt Reynolds. On Lowe's podcast, Oprah explained,
"This is when I was younger [...] 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 that specific question Field took issue with and not the overall topic,
as she's been candid about her relationship with Reynolds in other interviews.
Lance Armstrong is best known for his cycling career. During his peak,
he won the Tour De France an unprecedented seven times in a row, though it was later discovered
that he had been using performance-enhancing drugs. After this information came to light,
he was 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, he 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 admitted to a number of things, including:
"Did you ever take banned substances to enhance your cycling performance?"
"Did you ever blood dope or use blood transfusions
to enhance your cycling performance?" "Did you ever use any other banned
substances, like testosterone, cortisone, or human growth hormone?"
"Yes."
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 following the scandal. He also took
the opportunity to reflect on his discussion with Oprah. He stated:
"That interview came at
an interesting time and a difficult time, and maybe in a lot of ways came too soon."
Regardless, he admitted that he knew legal trouble was coming and that he had to publicly come clean.
Author James Frey's acclaimed memoir about his personal experiences with addiction,
titled "A Million Little Pieces," was published in 2003. Selecting
the bestseller for her book club, Oprah Winfrey told her audience,
"It's a gut-wrenching memoir that is raw and it's so real."
But 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. She stated:
"I don't know what is true, and I don't know what isn't."
Frey was clearly uncomfortable during the interview. Feeling deceived,
Oprah was in an unusual state herself. She later reflected on the controversial chat, saying,
"I was pretty defensive. I was defending my turf."
Oprah felt responsible for every single viewer who had bought the book. However,
upon reflection, she realized that she had lost
her ability to interrogate her subject without judgment. As she explained,
"I've always tried to [...] see that person as
a human being and look at them with some sense of compassion."
"And I did not do that with James Frey."
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, and I was surprised by it."
NFL quarterback Drew Brees is best known for his talent on the football field. He
even earned MVP after winning the 2010 Super Bowl. Upon his historic win, Brees visited
"The Oprah Winfrey Show" for an interview. But after both Brees and Oprah sat down,
the host leaned over to her guest, wiped his cheek, and asked who kissed him,
mistaking the mark on his face for some lipstick. 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, you know, which I was obviously born with,
I got all kinds of comments when I was a kid."
He continued to explain that he dealt with the teasing, but it eventually turned
into a badge of honor. In fact, some fans mark their own faces as an homage to him.
"I guess we come full circle from, you know, from maybe a little bit of bullying when I
was a kid because of the birthmark and now you know people wanting to emulate that."
In 2005, to promote the movie "Crash," Oprah had the cast of the Oscar-winning film and director
Paul Haggis on her show. While most of the film's stars 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,
accusing her of editing out many of his responses in favor of her own. He explained,
"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."
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. He lamented,
"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."
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. He explained,
"She was completely against everything that was
in my music. So she ain't never going to have me on that show."
The rapper added that he was eager to be interviewed by the TV host because
it would 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,
and he and Oprah eventually enjoyed the chat he'd always dreamed of. He told People,
"We finally met, and my grandmother and I went on the show. 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."
Another rapper who found fault with Oprah is Ice Cube. In 2006,
he complained to FHM that the media mogul made him feel left out. He shared,
"I've been involved in three projects pitched to her, but I've never been asked to participate."
Ice Cube also noted that he's never been asked to be interviewed by Oprah. 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 Ice Cube wasn't invited to her
prestigious Legends Ball in 2006 despite his production company seemingly being involved,
Eisner suggested there must have been some conflict between the two. However,
Ice Cube claims he's unaware of any problem and still has yet to speak with her about it.
"I'm fine with that, you know, I've gotten this far without Oprah, so, I'm not worried about it."
Still, Ice Cube said that it would've been nice to represent his company's
work if he had been invited. As of 2023, he still is yet to be interviewed by Oprah.
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
film … 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. She stated,
"So now nobody's going to touch Mo'Nique because Oprah Winfrey said nothing."
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 she had respect
for Oprah's considerate approach, her feelings soon changed once she saw ads revealing that
her mom, dad, and other brother were also featured in the episode. She explained,
"Had Oprah Winfrey said, I'm gonna have your mother,' I would've said, 'Shut it down.'"
Elizabeth Taylor is one of the 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.
Prior to their meeting, Taylor told the host she wouldn't answer any questions
about her romantic history. So when Oprah attempted to broach the off-limits topic,
Taylor quipped, "None of your business." The host 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."
Unfortunately, this didn't work. Later reflecting on the interview, Oprah shared on Oprah.com,
"It's still painful to watch. For many reasons — including my bad hair."
In 2009, legendary comic Jay Leno 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. Oprah asked,
"Did you ever ask yourself, 'Well, am I being selfish?'"
Leno was quick to suggest that he considers whether he's being selfish or not daily,
and in this instance, he didn't think he acted out of selfishness. He explained,
["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." https://youtu.be/nHdCWKSPSP8?t=149]
Bringing up the rumors that Leno had sabotaged O'Brien's show to steal it back from him,
Oprah made her position clear, stating:
"I'm really surprised that so many people are against
you because I think that people don't understand the way television works."
In the '90s and early 2000s, few young stars were as popular as Mary-Kate and
Ashley Olsen. Their careers began when they were infants sharing the role of
Michelle Tanner on "Full House" for the sitcom's entire eight-season run. In 2004,
the two appeared on "The Oprah Winfrey Show" for the first time, but the interview took
an uncomfortable turn when the host addressed speculation that Mary-Kate had an eating disorder.
"I know there's a new rumor has recently surfaced that has really upset you, right?
You know, the one about eating."
After an awkward pause, 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."
But she was interrupted by Oprah.
"What size are you, by the way?"
"Size?"
The twins were shocked Oprah even asked such a question.
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.