Oprah Winfrey has conducted tens of thousands of interviews over the course of her prestigious
career, and a few of them stand out for making viewers cringe.
Keep watching to experience the most uncomfortable Oprah interviews ever!
During a 2003 interview with Barbra Streisand, Oprah noticed something was amiss.
Streisand had made a bold sartorial move, wearing a white turtleneck, and also accessorizing
with her tiny, white dog named Sammie.
But that wasn't all.
Oprah bluntly called Streisand out on not only matching her turtleneck to her dog…but
also her microphone, which was also white.
"I want to just say this before we go to...I, I've never, I own this studio, I've been here,
I don't know how many years.
I've never seen a white mic."
As she sat in a Bond villain-esque pose, Streisand promptly corrected Oprah.
"It's actually off-white, to match my off-white sweater."
So, why was Oprah questioning the mic color choice?
Turns out the mic belonged to Oprah, and Streisand had it modified to suit her outfit without
asking.
Oprah lost a mic, and gained one awkward commercial break.
"Okay, so you had the mic sprayed?"
"That's right."
"Okay, we'll be right back, we'll be right back."
In a 2006 interview with the Associated Press, rapper 50 Cent expressed beef with Oprah Winfrey,
claiming she wouldn't have rappers on her show because she, quote, "caters to older
white women."
Cut to six years later, and Fitty's comments were looming large when he sat down with Oprah.
The pair slowly but surely unpacked the rumored feud, and in a moment that saw the rapper
sweating in the hot seat, Oprah confronted him about the fact that he named his dog after
her, saying,
"Okay, but you named your dog Oprah, that was not the compliment."
50 Cent seemed a little embarrassed, but he managed to explain why he chose the name.
"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."
Thankfully, everything was apparently squared away by the end of the conversation.
"So now, do you have greater affection for me?"
"Absolutely."
When Oprah announces a selection for her Book Club, it's all but guaranteed to hit bestseller
lists.
In 2005, she chose James Frey's harrowing memoir A Million Little Pieces, which is about
the author's struggles with alcoholism.
But then the website The Smoking Gun unearthed evidence that Frey had fabricated aspects
of his story.
Oprah invited Frey onto her show to explain himself.
The ensuing conversation makes for seriously nerve-racking viewing as an obviously ticked
off Oprah took aim at the author with precision.
"I wanted to start with the Smoking Gun report titled 'The Man Who Conned Oprah,' and I want
to know, were they right?"
But ultimately this is a story of forgiveness.
In 2011, Oprah invited the author back to her show to make amends, telling him that
despite the falsities in the book, it had helped other people dealing with addiction.
During Oprah's January 2013 interview with disgraced cyclist Lance Armstrong, she confronted
him with incredibly direct questions about his use of performance-enhancing drugs.
One of the most cringe-inducing moments occurred when Armstrong attempted to make a joke about
Betsy Andreu, the wife of his former cycling teammate, Frankie Andreu.
Betsy had publicly criticized Armstrong for lying about his drug use, so Oprah asked Armstrong
about things he'd reportedly said about her.
"I'm gonna take the liberty to say it, and I said, 'Listen, I called you crazy.
I called you a b----.
I called you all these things, but I never called you fat.'"
As Armstrong waited for a laugh from Oprah at what he seemed to consider an amusing anecdote,
the camera instead just cut to a shot of her keeping her gaze sharply fixed on him.
What made this interview so uncomfortable was that, despite Armstrong admitting that
he used illegal substances, he didn't show much remorse for the pain he'd caused others.
Actress and musician Mackenzie Phillips dropped a bombshell during a 2009 Oprah Winfrey Show
appearance.
Along with candidly talking to Oprah about her struggles with drug addiction and her
troubled childhood, Phillips read a passage from her memoir, High on Arrival.
She described a ten-year long incestuous relationship with her father, John Phillips, who was the
leader of the '60s rock band The Mamas & The Papas.
Phillips' revelation spawned conflict within her own family.
In 2016, she returned for a segment on OWN's Where Are They Now, in which she discussed
the terrifying experience wrought by that original interview.
"But then in retrospect, I realized there was some due diligence that I missed doing."
"Like what?"
"Like preparing myself for losing my family."
Oprah had an excruciatingly uncomfortable interview with Hollywood legend Elizabeth
Taylor on February 1st, 1988.
A subdued Taylor was noticeably withholding throughout the conversation.
Prior to the interview, she had requested that there be no questions about her relationships,
a rule that Oprah did not abide by.
The actress replied to one probing inquiry with a terse,
Taylor was so reserved that Oprah couldn't help but tease her by saying,
As recounted on Oprah.com, part of the reason the interview was so awkward was because Taylor
was suffering from hip and back pain at the time.
Despite this memorably awkward exchange, the actress continued to make more appearances
on The Oprah Winfrey Show over the years.
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