Oprah is a lot of things — mogul, iconic life coach, movie producer,
magazine publisher, and spiritual conduit , just to name a few. But you don't whip
up a billion-dollar empire without ruffling some feathers along the way. From actors,
to authors, to musicians and royalty, these are the most controversial Oprah interviews ever.
"You all are gonna have to calm yourselves."
This notorious interview
from The Oprah Winfrey Show wasn't talked about for years after the fact because of
any jaw-dropping revelation or uncomfortable truth bomb — it was just sort of…weird.
"Please welcome Tom Cruise!"
Tom Cruise popped up on the show in 2005 to promote his big-budget remake of The War
of the Worlds. But that was all quickly forgotten after the topic turned to the
relationship he'd recently begun with Dawson's Creek star, Katie Holmes. Oprah could barely
get any actual questions out because of Cruise's physical demonstration of his romantic feelings.
"On the sofa, off the sofa, on the sofa, off the sofa."
An excitable studio audience full of fans ate it
all up — happily screaming at every one of the actor's unpredictable movements.
"Something happened to you!"
"I'm in love."
Critics of the chat weren't so complimentary,
however. The Ringer said it, quote, "rocked Hollywood," claiming that
it transformed the way audiences digest celebrity content — and not in a good way.
According to Oprah.com,
90 million people tuned in for her 1993 primetime interview with Michael Jackson.
It was the pop star's first chat in 14 years, and he used the opportunity to clear
the air on some of the more controversial elements of his lifestyle and appearance.
"That's the most ridiculous, horrifying story I've ever heard. It's crazy."
If viewers wanted answers, they got them. Jackson said that his lighter skin wasn't
the result of cosmetic skin bleaching, but rather the effect of a genetic skin
disease called vitiligo . Nor did he sleep in a "hyperbaric chamber" to look young;
a circulated photo of Jackson laying in the device was real, but he was just testing it
out before donating one to a burn center. He also claimed that the reason he struck
up friendships with children, and hosted them at his home with an on-site amusement park,
was compensation for his own lost childhood, spent performing as a member of the Jackson 5.
"I just simply want to be loved wherever I go."
One thing Jackson refused to discuss on national TV, however,
was his love life. He claimed to be dating Brooke Shields at the time,
at which point Oprah flat out asked Jackson if he was a virgin. He said,
"I'm a gentleman, that's something that's private.
You can call me old-fashioned if you want, but to me that's very personal."
By 1988, two-time Academy Award winner Elizabeth Taylor wasn't the major movie star she once was.
She appeared in the occasional TV show or miniseries, but she still dominated the tabloids
because of her active romantic life — at the time, she'd clocked seven marriages to six men.
"I'm a very committed wife. I should be committed, too, for being married so many times."
The New Yorker reported that when Oprah landed an interview with Taylor, it was the first major
celebrity sitdown for The Oprah Winfrey Show. But the host refused to follow one rule agreed
upon before the chat: no questions about Taylor's love life. When Oprah tried to ask about Taylor's
romances, Taylor replied, quote, "none of your business." And many of her other answers were
short and terse, making for really bad TV. At one point Oprah tried to cut the tension by quipping,
"You're so revealing — you just tell everything! I declare,
you've got to stop talking so much, Ms. Taylor."
While Taylor would call the encounter the, quote,
"worst interview of my life," she later apologized, citing hip and back pain as
the reason for her foul mood. She returned to the show in 1992 in much better spirits.
"It was in all the papers that I had died. I've never had such good reviews."
Oprah's Book Club launched in 1996 — a segment of her talk show that made any
selection an instant bestseller. In 2005, the host picked A Million Little Pieces,
a brutal and painful memoir by James Frey about his years-long struggle with
drug addiction. The work became the bestselling nonfiction book of the year,
and Frey appeared on the show to discuss the story that Oprah called, quote, "gut-wrenching."
But in early 2006, The Smoking Gun ran an exposé , revealing that Frey had made up a large portion
of his so-called memoir. For example, he didn't have any part at all in a story he told about a
fatal train crash that claimed the lives of two teenagers. Weeks after the story broke,
Frey returned to The Oprah Winfrey Show to face angry viewers and a livid host. She said,
"I feel duped. But more importantly, I feel that you betrayed millions of readers."
"I don't know what is true, and I don't know what isn't."
Attempting to explain why he lied within the pages of his book, Frey tried in vain to make excuses,
arguing that he, quote, "altered" a lot of details but that the overall plot of the memoir was true.
The chat was so controversial, Oprah even later apologized to Frey for not treating
him with the empathy she reserved for other guests, regardless of the mistakes they'd made.
"My position and intention was, 'How dare you."
"It really was not a position of, 'Let me hear your story.'"
In 2004,
NBC announced that Late Night host Conan O'Brien would take over The Tonight Show
from Jay Leno...in five years time. But when the time came, NBC didn't want to lose Leno
to a rival network, so they gave him a nightly talk show in primetime. The Jay Leno Show failed,
and The Tonight Show with Conan O'Brien wasn't a ratings hit, so by early 2010, NBC had dismissed
O'Brien and reinstalled Leno at Tonight. Leno became publicly perceived as the villain of this
late night shift — an affable guy on camera, but a cutthroat careerist manipulator behind the scenes.
"We don't hate each other. The media makes a big thing about it."
Oprah invited Leno on to her show to tell his side of the story, but he didn't do much to save face.
He wrote off the Tonight Show drama as a, quote, "huge mess" and then played the victim card,
claiming he felt brutalized by the backlash. He also admitted that when he announced his eventual
retirement in 2004, he wasn't exactly serious about it. Then Leno passive-aggressively argued
that NBC was right to reinstall him, because under O'Brien's poor ratings, he claimed,
"[It marked] the first time in the 60-year history of The Tonight Show
that The Tonight Show would have lost money."
"Yeah, it's hugely embarrassing."
Leno's actions were so unpopular that a poll on
Oprah.com found that 96 percent of the audience sided with O'Brien.
Bestselling author Terry McMillan
based her novel How Stella Got Her Groove Back on her own story. Like the book's main character,
she was a successful, divorced, middle-aged woman who found love again with a man two
decades her junior. According to Oprah.com, in 1995, 43-year-old McMillan took a trip to
Jamaica and fell in love with 20-year-old Jonathan Plummer. Before long, he moved in
and they got married. But they split up in 2005 when Plummer revealed that he was gay, resulting
in a tabloid scandal — with both McMillan and Plummer bad-mouthing each other to the press
and Plummer successfully suing his former wife for spousal support despite their existing prenup.
"Did you feel, obviously, betrayed?"
"Yes. It is betrayal. And deception."
The fight between the two came to a head in public, and Oprah provided the forum,
hosting both parties on a 2005 episode of the show. Shortly after, McMillan sued
Plummer for $40 million, citing emotional distress and destruction of her reputation.
She won, but she never forced Plummer to pay. She ultimately decided to sue because she didn't want
fans to think her feelings toward her ex were born of any form of discrimination. She said,
"I was never trying to sue him for his money. He didn't have any."
Eventually, the two patched things up enough to return to Oprah in 2010 to discuss their divorce.
"I wouldn't trade those years with him for anything.
They were some of the best years of my life. I felt loved. I was loved."
In the spring of 1996,
the United Kingdom experienced an outbreak of what was commonly known as Mad Cow Disease.
Per the FDA, the disease destroys cows' central nervous system, and if humans eat infected beef,
they can contract a deadly variant of the disease. During the Mad Cow scare,
Oprah booked former cattle rancher, Howard Lyman, who had since adopted a vegetarian lifestyle and
gone to work for the Humane Society's Eating with Conscience animal welfare campaign.
He appeared on the show to discuss the threat of Mad Cow to Americans, pointing out that
feeding the remains of Mad Cow-infected cattle to other animals could have facilitated the spread.
And that such practices were common in the U.S. Oprah was stunned, stating,
"It has just stopped me cold from eating another burger."
Just hours after her hamburger-damning declaration, the price of beef futures
plummeted, and stayed low for two months. One Texas rancher lost an estimated $6.7 million
and organized a class action libel lawsuit against Oprah and
her show's producers for damaging the reputation of American beef.
"I'm not a manipulator, I'm not a liar, I did not say that to destroy the beef industry."
After a six-week trial, during which time production of The Oprah Winfrey
Show relocated to Texas, Oprah won in what she called a, quote, "victory for free speech."
When people tune in to a tell-all TV interview with a celebrity, they expect to be shocked. But
viewers were still likely unprepared for what happened when former One Day at a Time star
Mackenize Phillips appeared on the show in 2009 to promote her upcoming memoir High on Arrival.
"Here I was with this huge piece of information that
maybe wasn't even fit for public consumption."
She read aloud a passage describing how after waking up from a substance-induced blackout,
she discovered her father, John Phillips of the Mamas and the Papas, assaulting her.
She was 18 years old. When Mackenzie confronted him, he denied the incident,
but thus began — in parallel to a powerful drug addiction — a decade-long series of assaults.
While the revelation was deeply troubling, what really upset viewers is when Mackenzie said that
by the time she turned 29, the dynamic with her father had turned consensual,
to the point where the '60s rock star allegedly fantasized about secretly marrying his daughter.
Mackenzie finally walked away when she became pregnant and didn't know
if the father was her husband or her own dad. She ultimately terminated
the pregnancy. Her father passed away in 2001, eight years before she went public.
"I would have handled that interview completely differently,
had it not been a book that is published."
But Mackenzie's claims weren't just controversial to the show audience.
Her own family members cast doubt on the shocking allegations. As of 2017,
Mackenzie still claimed to be struggling with family fallout.
Lance Armstrong's story was an inspiring
tale of perseverance and human achievement. From 1999 to 2005, Armstrong won the grueling,
weeks-long Tour de France an unprecedented seven consecutive times. Even more impressive:
He did it after a cancer diagnosis and recovery. But Armstrong's athletic feat was soured when,
just after his 2005 Tour de France win and retirement from cycling, a French newspaper
published evidence that suggested Armstrong had used banned performance enhancers.
He denied the charge, something he would repeatedly do over the next three years,
as multiple teammates came forward to admit that they'd doped alongside Armstrong.
The writing was seemingly on the wall, but it was no less shocking when Armstrong finally
confessed to what amounted to cheating, on Oprah's Next Chapter, in 2013.
"Did you ever take banned substances to enhance your cycling performance?"
"Yes."
Oprah then asked whether he had used those substances to secure his record
seven Tour de France titles.
"In all seven of your Tour de France victories,
did you ever take banned substances or blood dope?"
"Yes."
Armstrong went from sports hero to public pariah in that instant. He said on the show,
"I'll spend the rest of my life trying to earn back trust and apologize to people."
As there are two young royal couples today,
so it was back in the '80s. Earning almost as much media coverage as Charles and Diana, there existed
Prince Andrew and the Duchess of York, Sarah Ferguson. Ferguson sat down with Oprah in 1996 to
discuss the harsh realities of life in Buckingham Palace. Just after her ten-year marriage to Prince
Andrew ended, Ferguson told Oprah that royal life was less "fairytale" and more of a joyless
slog adhering to meaningless rules. Of Buckingham Palace, for instance, she said,
"All the windows have to be only open only a certain amount so they are all in line,
and so of course, I'd come in and fling open all the windows. No, that was wrong."
Ferguson also detailed the nasty treatment she endured from the media, revealing,
"I must explain that the British press at the moment is completely
and utterly cruel and abusive. […] It is very cruel and very painful when you
are going to try and find the feelings within to be on such a public stage."
Ferguson would return to Oprah to express herself whenever scandal broke, such as when
she was caught accepting a bribe, and when she wasn't invited to William and Kate's wedding.
"The best is yet to come. Certainly. I guaran-damn-tee that for you."
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