12 of Oprah Winfrey's Most Controversial Interviews – From Cindy Crawford to Michael Jackson

Cindy Crawford broke her silence nearly four decades after her "awkward" interview with Oprah Winfrey on The Oprah Winfrey Show.

In the new Apple TV+ documentary series The Super Models, Crawford recalled the 1986 interview she had when she was starting in the fashion industry. The model, now 57, revisited the time Winfrey asked to display her physique – something she did not expect from the host.

"When you look at it through today's eyes when Oprah's like, 'Stand up and show me your body. Like, show us why you're worthy of being here,'" she continued. "In the moment, I didn't recognize it. Only when I look back at it, and I was like, 'Oh my gosh. That was so not OK, really.' Especially from Oprah."

Like Crawford, Elizabeth Taylor did not have the best experience during her interview with Winfrey.

Before the February 1, 1998 discussion, the Father of the Bride actress reportedly set preconditions prior to her appearance to promote her book, Elizabeth Takes Off, which Winfrey refused to follow. Instead of focusing on the book alone, the host asked her about her romantic entanglements.

Taylor, who died on March 23, 2011, asked Winfrey not to speak about her past relationships and told her, "None of your business."

"You're so revealing — you just tell everything! I declare, you've got to stop talking so much, Ms. Taylor," Winfrey quipped to ease the awkward and tense moment.

When Jay Leno suffered backlash for allegedly "stealing" The Tonight Show from Conan O'Brien after The Jay Leno Show flopped, Winfrey invited him to her show so he could share his side of the story.

The now-73-year-old host said during his appearance that he felt "sucker-punched" by the criticisms and that his announced retirement was a white lie. Leno tried to defend himself throughout the interview, but a poll conducted on Oprah.com revealed that 96 percent of the audience sided with Conan.

Embattled cyclist Lance Armstrong tried to clear his name when he spoke to Winfrey about using performance-enhancing drugs.

The host asked him several questions, including "Did you ever take banned substances to enhance your cycling performance?" and "In all seven of your Tour de France victories, did you ever take banned substances or blood dope?"

Armstrong quickly answered "yes" to the queries, admitting his wrongdoing and proclaiming he would spend the rest of his life apologizing to people.

The cyclist insisted that he was not doping when he returned in 2009, but the U.S. Anti-Doping Agency CEO, Travis Tygart, said Armstrong lied again.

"Just contrary to the evidence...His blood tests in 2009, 2010 — expert reports based on the variation of his blood values — from those tests, one to a million chance that it was due to something other than doping," said the CEO.

Winfrey's audience was shocked when Mackenzie Phillips detailed her relationship with her father.

In the 2009 interview, Phillips revealed that John Phillips raped her following a substance-induced blackout. She confronted her father about it, but he denied it and insisted they made love.

After the incident, the 10-year assault began.

"It didn't happen every day, it didn't happen every week, but it certainly happened many times," she told Winfrey. "If you're me, you box it away. It's one of those things where you tell yourself don't look. There's a video reel playing in my head, and I've spent 30 years trying not to look."

When she turned 29, the relationship reportedly turned consensual as she suddenly felt love for her father. However, her pregnancy – which she terminated – led her to walk away.

The interview attracted criticism not only from Winfrey's audience but also from Phillips' family.

On March 7, 2021, CBS aired the initial broadcast of Prince Harry and Meghan Markle's tell-all interview with Winfrey. The highly-anticipated discussion left fans enraged, as the couple targeted the royal family for the first time in public.

It also stirred controversies because of Prince Harry and Meghan's accusations against the royals, including the racism that reportedly lingered around them and their eldest child, Archie, when they were still in the U.K.

They also spoke about the rifts within Prince Harry's family, including his feud with his older brother, Prince William.

After the interview, Buckingham Palace expressed the royal family members' sadness over the couple's alleged challenging years.

"The issues raised, particularly that of race, are concerning," the palace said. "While some recollections may vary, they are taken very seriously and will be addressed by the family privately. Harry, Meghan and Archie will always be much-loved family members."

Winfrey launched Oprah's Book Club in 1996 and welcomed James Frey's book, A Million Little Pieces, in September 2005. The memoir contains his stories about his drug and alcohol addictions and what happened during his time at a treatment center.

The host promoted the book and said she could not put down the "gut-wrenching memoir that is raw and it's so real…"

But in January 2006, The Smoking Gun dropped a shocking exposé about how the American writer exaggerated and fabricated a huge part of the book.

Weeks later, the author returned to The Oprah Winfrey Show to face everyone and apologize for the deception.

"I don't have a whole lot of respect for the genre," he explained during his reappearance. "I think most writers of memoirs, and this is a very unpopular statement, do what I did."

Michael Jackson tried to set the record straight in his 90-minute interview with Winfrey, but he ended up sparking more unanswered questions.

The lengthy discussion, which drew over 90 million viewers, featured several revelations by the "Smooth Criminal" singer, including his admission to cosmetic surgery, his vitiligo diagnosis and his relationship with his father.

Terry McMillan and Jonathan Plummer's tirades against each other continued on a Winfrey-hosted forum in a November 2005 episode of The Oprah Winfrey Show. The host allowed the How Stella Got Her Groove Back author to confront her gay ex-husband for the distress and damages he caused.

"I told him him, 'We're not gonna be sitting on a rocking chair on the back porch together,'" McMillan said at one point in the discussion. "My attitude is this: happiness is as long as it lasts, and as long as two people work to make it work. And Jonathan was young, and I said, 'You know what? I didn't want to steal your 20s from you.'"

The estranged couple eventually patched things up after going through a legal battle and returned to Winfrey's show in 2010.

In 2005, the wild Tom Cruise surprised the viewers of Winfrey's show when he appeared with full-blast energy by jumping on the couch and punching the floor while confessing his love for Katie Holmes.

"What has happened to you?" Winfrey asked, to which Cruise responded, "I'm in love."

In Seth Rogen's book Yearbook, the comedian wrote that the Mission: Impossible actor told him it was a coordinated effort and a "heavily edited" appearance to shed a negative light on him.

"They're scrambling and they're doing everything they can to discredit me so I won't hurt sales anymore," Cruise reportedly added.

In 1996, Sarah Ferguson sat down with Winfrey and shared what her life looked like inside Buckingham Palace. At that time, her marriage to Prince Andrew ended. The Duchess of York said her royal life was not a fairy-tale.

"I must explain that the British press at the moment is completely and utterly cruel and abusive and so invade," she said. "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."