Top 10 Most Controversial Oprah Moments

In August 2023, deadly wildfires ravaged the island of Maui in Hawaii, causing billions in damage and sadly claiming over a hundred lives. In response, Oprah Winfrey and Dwayne Johnson launched the People’s Fund of Maui to raise money for the victims. They announced the fund on social media, kicking it off with $10 million of their own money, but were met with intense criticism. Many wondered why Winfrey, a billionaire, and Johnson, a multimillionaire, were asking everyday people to donate instead of digging deeper into their own pockets. Some suggested they direct their appeals towards their wealthy friends instead. Despite the backlash, Winfrey stood by the fund, calling it a “really strong idea,” although she admitted feeling “vilified online.”

Back in 2004, famous twins Mary-Kate and Ashley Olsen were interviewed on “The Oprah Winfrey Show.” Rumors had been circulating that Mary-Kate was dealing with an eating disorder, and Winfrey brought up the topic during the interview. Ashley quickly dismissed these rumors, however, stating that they weren’t concerned with tabloid gossip. Undeterred, Winfrey probed even further, asking an inappropriate question about their weight that left the teenage sisters visibly uncomfortable. Though there was little public reaction at the time, the interview stirred controversy when it resurfaced in 2021. Internet users slammed Winfrey for the intrusive questions, noting that the twins were minors at the time and Mary-Kate had to seek treatment later that year for an eating disorder.

There have hardly been public declarations of love as exuberant as this one. In 2005, Hollywood action star Tom Cruise appeared on “The Oprah Winfrey Show” to promote his film “War of the Worlds.” The discussion swiftly shifted from the movie to Cruise’s personal life and his recent relationship with actress Katie Holmes. As Cruise expressed his affection for Holmes, he began displaying a series of strange behaviors, including the now-famous moment when he jumped onto the studio couch. It was so bizarre that the typically composed Winfrey appeared to be at a loss for words. The clip immediately went viral, at a time when video-sharing platforms on the internet were still in their infancy.

Oprah Winfrey is undeniably influential, a fact that was demonstrated in the 2008 presidential election. Her endorsement of Barack Obama during the Democratic primaries played a significant role in his eventual win. Despite her clear preference, Winfrey decided not to invite any candidate to her show during the campaigns. This became a hot topic in September 2008 when The Drudge Report alleged there was behind-the-scenes drama about inviting Republican Vice Presidential candidate Sarah Palin. Winfrey refuted these claims, but stood firm on her decision to not interview Palin until after the elections, which she eventually did. This move drew criticism from some fans who accused her of bias, pointing out that she hosted Obama twice on her show before he announced his candidacy.

Michael Jackson’s personal life was the subject of countless bizarre rumors, yet for years, he avoided addressing them. That changed in 1993. That February, Jackson sat for an interview with Oprah Winfrey that attracted over 60 million viewers in the U.S., making it the most-watched TV interview in the country’s history. Winfrey’s questions covered topics like whether Jackson slept in an oxygen chamber, bought the remains of Elephant Man, and if he bleached his skin because he didn’t like being Black. Perhaps the most controversial moment came when Winfrey inquired if Jackson was still a virgin. This interview offered a rare glimpse into Jackson’s private world and was one of the last times audiences saw him before the sexual assault allegations emerged.

Oprah Winfrey has long been open about her weight loss journey. In 1988, she created one of the most unforgettable moments on her show. Winfrey unveiled her new slim figure by whipping off an oversized coat and wheeling out a wagon holding 67 pounds of animal fat, the amount she had lost in less than five months. She achieved this by running 6.5 miles a day and relying solely on a liquid diet. The episode drew huge attention, earning the highest ratings in the show’s history. However, years later, Winfrey expressed regret about it, stating that it was simply an ego trip and admitting that she eventually regained all of the weight.

Author James Frey released his debut novel “A Million Little Pieces” in April 2003. Chronicling his intense experience with substance use disorder and rehabilitation, the book initially received mixed reviews. It wasn’t until September 2005 when Oprah selected “A Million Little Pieces” for her Book Club that it became a cultural phenomenon, topping the New York Times Bestseller List for 15 consecutive weeks. But controversy soon struck. An investigative website alleged that Frey had fabricated major details in the book. Oprah initially stood by Frey, but later invited him on her show, where she grilled him about the allegations before a disappointed audience. Frey ultimated owned up to it, attributing his dishonesty to the same demons that drove him to drugs.

Over its 25-year run, “The Oprah Winfrey Show” featured an incredible variety of guests, from the most beloved celebrities to a gang of skinheads from the KKK. In the 1990s, Winfrey invited the group of klan members, hoping to change their minds about Black people. This apparently backfired, as the men used her highly popular show as a platform to spout their reprehensible ideologies. Realizing this mistake, Oprah decided to steer clear of the sensational tabloid topics that were prevalent in trash TV shows of that era. This marked a turning point for the show, which then began to focus more on uplifting, educational and philanthropic themes.

In 2003, the U.S.-led decision to invade Iraq sparked huge protests around the world and sharply divided public opinion. One of its prominent critics was Oprah Winfrey, who aired a series of controversial anti-war episodes between November 2002 and March 2003. The most notable of these was a two-day special, “The World Speaks Out On Iraq,” featuring highly influential figures like Nelson Mandela and Pope John Paul II, who spoke against the war. Anti-war advocates praised the show, while people who supported the invasion heavily lambasted it. The first part of the special was notably interrupted by a White House press conference, which many saw as an intentional attempt by the Bush administration to silence Winfrey’s anti-war message.

In 1996, Oprah Winfrey welcomed Howard Lyman, a former cattle rancher turned animal rights activist, onto her show. This discussion that day revolved around a controversial practice in the beef industry called rendering, in which animal tissues are ground up to make cattle feed. As this occurred during the “mad cow panic,” Lyman’s revelations prompted Winfrey to declare that she would stop eating hamburgers. Right after the episode aired, beef prices plummeted for almost two weeks, hitting a 10-year low. As a result, a group of Texas cattle ranchers sued Winfrey for $10.3 million, alleging that her remarks caused undue harm to the entire beef industry. Following a highly publicized trial in Texas, the jury found Winfrey not liable for defamation.

What other controversial Oprah moments did not make our list? Let us know in the comments below.