The Most Controversial Oprah Interviews Ever

Oprah Winfrey is a lot of things — mogul, life coach to millions, movie producer, book recommender, magazine publisher, and spiritual conduit to name just a few. She's the American dream in action, having grown up in poverty and suffering numerous traumas to become a journalist, TV personality, and, in the 1980s, the most successful daytime talk show of all time. The Oprah Winfrey Show aired to millions of devoted viewers each day, looking to Winfrey for advice, guidance (and maybe a new car or free stuff) on how to be their best and complete selves. The Oprah show went off the air in 2013, having evolved away from its original premise: standard daytime talk show, where Oprah would interview celebrities, newsmakers, and regular people with a story to tell.

Until the blockbuster, monarchy-rattling 2021 primetime joint interview Winfrey conducted with Prince Harry and Meghan Markle, it was easy to forget that Winfrey is one of the most probing, sensitive, and curious interviewers on TV. Usually the interviews went well and made for great entertainment. Other times, these interviews with headline-grabbers made the news themselves. Here are the most scandalous and salacious interviews Oprah Winfrey ever conducted.

This infamous interview from The Oprah Winfrey Show wasn't talked about and analyzed for years after the fact because of any jaw-dropping revelation or uncomfortable truth bomb — it was just sort of weird, what with a usually well-composed A-list movie star ignoring the unofficial rules of talk show decorum.

Tom Cruise popped up on The Oprah Winfrey Show in 2005, ostensibly to promote his big-budget, big-screen remake of The War of the Worlds, according to The Ringer. That was all quickly forgotten after the topic turned to the relationship he's recently started with Dawson's Creek star Katie Holmes, and goodness, did he like her. Winfrey can barely get any actual questions out because of Cruise's physical demonstration of his romantic feelings. At various times, Cruise jumps out of his seat, throws his arms in the air, pumps his fists, falls to his knee, slaps the ground, squirms, and tries to walk it all off. An excitable studio audience full of Cruise fans loves it — his energy is infectious and they happily scream at every one of the actor's unpredictable movements. "Something happened to you!" a delighted Winfrey exclaims at one point. "I'm in love," Cruise explains. He punctuated that remark, and somehow also proved it, by jumping on Winfrey's yellow couch... twice.

Critics of the chat weren't so sure, however, with The Ringer saying it "rocked Hollywood" and became "a turning point for how we discuss and understand celebrities" — and not in a good way. 

According to Oprah Winfrey's website, 90 million people watched her February 1993 live, primetime interview with Michael Jackson. It was Jackson's first chat in 14 years, and he used the opportunity to dispel rumors and explain some of the more controversial elements of his lifestyle and appearance. If viewers tuned in for answers, they got them. Jackson said that his noticeably and gradually lightening skin wasn't the result of cosmetic and elective skin bleaching, but an 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 working as a member of the Jackson 5.

Jackson also opened up about the abuse he suffered as a child at the hand of his father and former manager, Joe Jackson. One thing Jackson refused to discuss with Winfrey: his love life. He claimed to be dating Brooke Shields, and Winfrey flat out asked Jackson if he was a virgin. "I'm a gentleman, that's something that's private," he said. "You can call me old-fashioned if you want, but to me that's very personal."

By February 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 tabloids and celebrity magazines because of her active romantic life — seven marriages to six men by then, per ABC News.

The New Yorker reported that when Oprah Winfrey landed an interview with Taylor, it was the first major celebrity sitdown for The Oprah Winfrey Show, and it was a big deal, but the host refused to follow one rule agreed upon before the chat: no questions about Taylor's love life. When Winfrey tried to ask about Taylor's romances, Taylor replied "none of your business" and delivered a steely, withering stare. Many of her other replies, according to Oprah, were short and terse, making for bad, boring, and hostile television. At one point Winfrey deftly 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 Winfrey encounter "the worst interview of my life," she apologized, citing hip and back pain as the reason for her mood.

According to History, Oprah Winfrey launched Oprah's Book Club in 1996, a reading-encouraging segment of her talk show that made any selection a bestseller. In September 2005, Winfrey picked A Million Little Pieces, a brutal and painful memoir by James Frey about his years-long struggle with drug addiction. A Million Little Pieces became the bestselling nonfiction book of the year, and Frey appeared on The Oprah Winfrey show to discuss the work that Winfrey called "gut-wrenching."

In January 2006, however, The Smoking Gun ran an exposé, discovering that Frey had made up or juiced large swaths 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 Oprah. "I feel duped," she said (via Today). "But more importantly, I feel that you betrayed millions of readers," she added, also rhetorically asking Frey why he "felt the need to lie." Frey stammered and tried in vain to make excuses, arguing that he'd "altered" a lot of details but that the overall plot of the memoir was true, to which the studio audience responded with boos, gasps, and groans.

The cringeworthy interview was so controversial, Winfrey even later apologized to Frey for not treating him with the empathy she reserved for other guests, regardless of the mistakes they'd made. 

In 2004, NBC announced (via MarketWatch) 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. 

Oprah Winfrey invited Leno on to her show to tell his side of the story (via EW), and he didn't do much to save face. He wrote off the Tonight Show drama as "a huge mess" and then played the victim card, claiming he felt "sucker-punched" by the backlash. He also admitted that when he announced his eventual retirement in 2004, it was "a white lie." Then Leno circuitously and passive-aggressively argued that NBC was right to reinstall him because under O'Brien's poor ratings, it marked "the first time in the 60-year history of The Tonight Show that The Tonight Show would have lost money.

Leno's actions in the whole debacle were so unpopular that a poll on Winfrey's website conducted in conjunction with the interview 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 with McMillan and they married. They split up in 2005 when Plummer revealed that he was gay. That resulted 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 having signed a prenuptial agreement.

The fight between McMillan and Plummer came to a head publicly, and Oprah Winfrey provided the forum, hosting both on a November 2005 episode of The Oprah Winfrey Show, which allowed McMillan to confront Plummer and let out all of the pain and anger she'd been feeling. Shortly after, McMillan sued Plummer for $40 million, citing emotional distress and destruction of her reputation. She won, but didn't force Plummer to pay. She ultimately decided to sue because she didn't want the world to think her feelings toward her ex-husband were born of homophobia. "I was never trying to sue him for his money," she said. "He didn't have any." Eventually, the two patched things up enough to return to Oprah in 2010 to discuss their divorce.

In the spring of 1996, according to CBS News, the United Kingdom experienced an outbreak of bovine spongiform encephalopathy. More 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 called Creutzfeldt-Jakob disease. During the Mad Cow scare, The Oprah Winfrey Show booked Howard Lyman (above). The former cattle rancher had adopted a vegetarian lifestyle and went to work for the Humane Society's Eating with Conscience animal welfare campaign, and he appeared on the show to discuss the threat of Mad Cow to Americans. He pointed out (via The Independent) 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. Winfrey was left stunned. "It has just stopped me cold from eating another burger," she said.

The host's influence on her millions of viewers was such that just hours after her hamburger-damning declaration, the price of beef futures plummeted, and stayed low for two months. One Texas rancher, Paul Engler, lost an estimated $6.7 million and organized a class action libel lawsuit against Winfrey and her show's producers for besmirching American beef. (After a six-week trial, during which time production of The Oprah Winfrey Show relocated to Texas, she won.)

When people tune in to a tell-all TV interview with a celebrity known for their outlandish behavior and well-documented drug use, they expect to be shocked. Viewers of The Oprah Winfrey Show still likely weren't prepared for what happened when former One Day at a Time star and Mackenize Phillips appeared on the daytime show in 2009 (via CNN) to promote and discuss her soon-to-be-released memoir High on Arrival. 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, raping her. When Mackenzie confronted him, he denied assault and said they'd "made love," and thus began, in parallel to a powerful drug addiction, a 10-year-long series of assaults.

While that's all deeply troubling, what really upset The Oprah Winfrey Show 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. What prompted Mackenzie to walk away was when she got pregnant and didn't know if the father was her husband or her own father. She ultimately terminated the pregnancy.

Mackenzie's claims weren't just controversial to Oprah's audience. Her own family members, including her stepmother, Genevieve Waite, and half-siblings, Chynna and Bijou Phillips, cast doubt on the shocking claims. As of 2017, Mackenzie still claimed to be struggling with family fallout from her revelations. 

The story of Lance Armstrong was an inspiring tale of perseverance and human achievement. From 1999 to 2005, Armstrong won the Tour de France, a grueling weeks-long bicycle race, an unprecedented seven consecutive times. Even more impressive: He did it after a cancer diagnosis and recovery, according to ESPN. Armstrong's athletic feat was soured when, just after his 2005 Tour de France win and retirement from cycling, French newspaper L'Equipe published evidence that suggested Armstrong had used banned performance enhancing substances. 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 confessed to taking PEDs, and thus cheating, to Oprah Winfrey in January 2013 on Oprah's Next Chapter. Armstrong gave a quick "yes" to a rapid-fire series of questions from Winfrey, which included, "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 went from sports hero to public pariah in that instant. "I'll spend the rest of my life trying to earn back trust and apologize to people," Armstrong said on Oprah's Next Chapter (via BBC).

As there are two young royal couples today — Prince William and the Duchess of Cambridge, and Prince Harry and Meghan Markle — so it was back in the 1980s. Earning almost as much media coverage as Prince Charles and Princess Diana were Prince Andrew and the Duchess of York, Sarah Ferguson. And like how Markle's shocking accusations of royal family hostility and racism discussed in a 2021 interview with Oprah Winfrey, Ferguson sat down with Oprah in 1996 to discuss the harsh realities of life in Buckingham Palace. Just after Ferguson's ten-year marriage to Prince Andrew ended, she told Winfrey that royal life was "not a fairy tale," more of a joyless slog adhering to nitpick rules. Of Buckingham Palace, for instance, "the windows have to be open in only a certain amount so they are all in line, and I'd come in and throw open all the windows. And no, that was wrong," she said (via People).

Ferguson also detailed the nasty treatment she endured from the English media. "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." Ferguson would return to Winfrey's show 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.